TY  - JOUR
AU  - Tasić, Gordana
AU  - Mitrović, Nikola
AU  - Simić, Milena
AU  - Koravović, Mladen
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Jovanović, Miloš
AU  - Ivković, Branka
AU  - Savić, Vladimir
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5556
AB  - Hydantoin derivatives are versatile structural motifs found in natural products
and various compounds with different biological or other properties. Due to
their importance in both organic and medicinal chemistry, a number of synthetic procedures have been developed. In this article, a novel methodology
utilizing N-Boc protected amino acid amides for their preparation has been
described. The cyclisation process was accomplished using solid supported
PPh3 and CBr 4 as reagents affording substituted hydantoins in moderate to
good yields (40%–77%).
PB  - Wiley Periodicals LLC.
T2  - Journal Heterocyclic Chemistry
T1  - Synthesis of hydantoins from N-Boc protected aminoacid derived amides using polymer-supported PPh3/CBr4as a reagent
DO  - 10.1002/jhet.4802
ER  - 

@article{
author = "Tasić, Gordana and Mitrović, Nikola and Simić, Milena and Koravović, Mladen and Jovanović, Predrag and Petković, Miloš and Jovanović, Miloš and Ivković, Branka and Savić, Vladimir",
year = "2024",
abstract = "Hydantoin derivatives are versatile structural motifs found in natural products
and various compounds with different biological or other properties. Due to
their importance in both organic and medicinal chemistry, a number of synthetic procedures have been developed. In this article, a novel methodology
utilizing N-Boc protected amino acid amides for their preparation has been
described. The cyclisation process was accomplished using solid supported
PPh3 and CBr 4 as reagents affording substituted hydantoins in moderate to
good yields (40%–77%).",
publisher = "Wiley Periodicals LLC.",
journal = "Journal Heterocyclic Chemistry",
title = "Synthesis of hydantoins from N-Boc protected aminoacid derived amides using polymer-supported PPh3/CBr4as a reagent",
doi = "10.1002/jhet.4802"
}

Tasić, G., Mitrović, N., Simić, M., Koravović, M., Jovanović, P., Petković, M., Jovanović, M., Ivković, B.,& Savić, V.. (2024). Synthesis of hydantoins from N-Boc protected aminoacid derived amides using polymer-supported PPh3/CBr4as a reagent. in Journal Heterocyclic Chemistry
Wiley Periodicals LLC...
https://doi.org/10.1002/jhet.4802

Tasić G, Mitrović N, Simić M, Koravović M, Jovanović P, Petković M, Jovanović M, Ivković B, Savić V. Synthesis of hydantoins from N-Boc protected aminoacid derived amides using polymer-supported PPh3/CBr4as a reagent. in Journal Heterocyclic Chemistry. 2024;.
doi:10.1002/jhet.4802 .

Tasić, Gordana, Mitrović, Nikola, Simić, Milena, Koravović, Mladen, Jovanović, Predrag, Petković, Miloš, Jovanović, Miloš, Ivković, Branka, Savić, Vladimir, "Synthesis of hydantoins from N-Boc protected aminoacid derived amides using polymer-supported PPh3/CBr4as a reagent" in Journal Heterocyclic Chemistry (2024),
https://doi.org/10.1002/jhet.4802 . .

TY  - GEN
AU  - Stanković, Tijana
AU  - Ilić, Tanja
AU  - Petković, Miloš
AU  - Pantelić, Ivana
AU  - Dobričić, Vladimir
AU  - Cook, James M.
AU  - Savić, Miroslav
AU  - Savić, Snežana
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5578
AB  - The low aqueous and oil solubility of the novelpyrazoloquinolinone ligand (CW-02-79) with significantbinding affinity for sigma-2 receptors in the brain hindersthe development of conventional parenteral formulationsand thus a comprehensive evaluation of its efficacy andsafety. ...
T1  - Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5578
ER  - 

@misc{
author = "Stanković, Tijana and Ilić, Tanja and Petković, Miloš and Pantelić, Ivana and Dobričić, Vladimir and Cook, James M. and Savić, Miroslav and Savić, Snežana",
year = "2024",
abstract = "The low aqueous and oil solubility of the novelpyrazoloquinolinone ligand (CW-02-79) with significantbinding affinity for sigma-2 receptors in the brain hindersthe development of conventional parenteral formulationsand thus a comprehensive evaluation of its efficacy andsafety. ...",
title = "Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5578"
}

Stanković, T., Ilić, T., Petković, M., Pantelić, I., Dobričić, V., Cook, J. M., Savić, M.,& Savić, S.. (2024). Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation. .
https://hdl.handle.net/21.15107/rcub_farfar_5578

Stanković T, Ilić T, Petković M, Pantelić I, Dobričić V, Cook JM, Savić M, Savić S. Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation. 2024;.
https://hdl.handle.net/21.15107/rcub_farfar_5578 .

Stanković, Tijana, Ilić, Tanja, Petković, Miloš, Pantelić, Ivana, Dobričić, Vladimir, Cook, James M., Savić, Miroslav, Savić, Snežana, "Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation" (2024),
https://hdl.handle.net/21.15107/rcub_farfar_5578 .

TY  - CONF
AU  - Stanković, Tijana
AU  - Ilić, Tanja
AU  - Petković, Miloš
AU  - Pantelić, Ivana
AU  - Dobričić, Vladimir
AU  - Cook, James M.
AU  - Savić, Miroslav
AU  - Savić, Snežana
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5577
AB  - The low aqueous and oil solubility of the novel
pyrazoloquinolinone ligand (CW-02-79) with significant
binding affinity for sigma-2 receptors in the brain hinders
the development of conventional parenteral formulations
and thus a comprehensive evaluation of its efficacy and
safety. ...
PB  - International Society of Drug Delivery Sciences and Technology (APGI)
PB  - International Association for Pharmaceutical Technology (APV)
PB  - Italian Society of Technology and Legislation (S.T.E.L.F)
C3  - 14th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 18 - 21 March 2024, Vienna, Austria
T1  - Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5577
ER  - 

@conference{
author = "Stanković, Tijana and Ilić, Tanja and Petković, Miloš and Pantelić, Ivana and Dobričić, Vladimir and Cook, James M. and Savić, Miroslav and Savić, Snežana",
year = "2024",
abstract = "The low aqueous and oil solubility of the novel
pyrazoloquinolinone ligand (CW-02-79) with significant
binding affinity for sigma-2 receptors in the brain hinders
the development of conventional parenteral formulations
and thus a comprehensive evaluation of its efficacy and
safety. ...",
publisher = "International Society of Drug Delivery Sciences and Technology (APGI), International Association for Pharmaceutical Technology (APV), Italian Society of Technology and Legislation (S.T.E.L.F)",
journal = "14th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 18 - 21 March 2024, Vienna, Austria",
title = "Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5577"
}

Stanković, T., Ilić, T., Petković, M., Pantelić, I., Dobričić, V., Cook, J. M., Savić, M.,& Savić, S.. (2024). Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation. in 14th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 18 - 21 March 2024, Vienna, Austria
International Society of Drug Delivery Sciences and Technology (APGI)..
https://hdl.handle.net/21.15107/rcub_farfar_5577

Stanković T, Ilić T, Petković M, Pantelić I, Dobričić V, Cook JM, Savić M, Savić S. Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation. in 14th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 18 - 21 March 2024, Vienna, Austria. 2024;.
https://hdl.handle.net/21.15107/rcub_farfar_5577 .

Stanković, Tijana, Ilić, Tanja, Petković, Miloš, Pantelić, Ivana, Dobričić, Vladimir, Cook, James M., Savić, Miroslav, Savić, Snežana, "Overcoming the low solubility of novel pyrazoloquinolinone ligand (CW-02-79) by combination of drug-phospholipid complex and nanoemulsion technology: design and physicochemical evaluation" in 14th World Meeting on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, 18 - 21 March 2024, Vienna, Austria (2024),
https://hdl.handle.net/21.15107/rcub_farfar_5577 .

TY  - JOUR
AU  - Petković, Miloš
AU  - Kušljević, Dušica
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Savić, Vladimir
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5328
AB  - A cascade, metal promoted transformations utilizing chloro allenylamide, primary amine and aryl iodide afforded piperizinones in good yields. Under the optimized conditions the cascade is performed as one-pot process allowing formation of three bonds. The synthetic route, controlled by the reaction rates of several processes involved, introduces two points of diversity and is well suited for combinatorial synthesis or related technologies.
PB  - Georg Thieme Verlag
T2  - Synthesis
T1  - Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution
DO  - 10.1055/a-2201-9951
ER  - 

@article{
author = "Petković, Miloš and Kušljević, Dušica and Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena and Savić, Vladimir",
year = "2023",
abstract = "A cascade, metal promoted transformations utilizing chloro allenylamide, primary amine and aryl iodide afforded piperizinones in good yields. Under the optimized conditions the cascade is performed as one-pot process allowing formation of three bonds. The synthetic route, controlled by the reaction rates of several processes involved, introduces two points of diversity and is well suited for combinatorial synthesis or related technologies.",
publisher = "Georg Thieme Verlag",
journal = "Synthesis",
title = "Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution",
doi = "10.1055/a-2201-9951"
}

Petković, M., Kušljević, D., Jovanović, M., Jovanović, P., Tasić, G., Simić, M.,& Savić, V.. (2023). Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution. in Synthesis
Georg Thieme Verlag..
https://doi.org/10.1055/a-2201-9951

Petković M, Kušljević D, Jovanović M, Jovanović P, Tasić G, Simić M, Savić V. Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution. in Synthesis. 2023;.
doi:10.1055/a-2201-9951 .

Petković, Miloš, Kušljević, Dušica, Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena, Savić, Vladimir, "Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution" in Synthesis (2023),
https://doi.org/10.1055/a-2201-9951 . .

TY  - JOUR
AU  - Mitrović, Jelena
AU  - Divović-Matović, Branka
AU  - Knutson, Daniel E.
AU  - Petković, Miloš
AU  - Đorović, Đorđe
AU  - Ranđelović, Danijela V.
AU  - Dobričić, Vladimir
AU  - Đoković, Jelena
AU  - Lunter, Dominique J.
AU  - Cook, James M.
AU  - Savić, Miroslav
AU  - Savić, Snežana
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4434
AB  - Preclinical development of deuterated pyrazoloquinolinone ligands, promising drug candidates for various neuropsychiatric disorders, was hindered by unusually low solubility in water and oils. DK-I-60-3 (7-methoxy-d3- 2-(4-methoxy-d3-phenyl)-2,5-dihydro-3Hpyrazolo[4,3-c]quinolin-3-one) is one of such pyrazoloquinolinones, and we recently reported about increased oral bioavailability of its nanocrystal formulation (NC). Lipid nano- particles (LNP) with a high concentration of lecithin, which enhances loading capacity of the lipid matrix, may give rise to further improvement. After preformulation studies by differential scanning calorimetry and polarized light microscopy, LNP were prepared by the hot high pressure homogenization, and characterized in terms of particle size, morphology, and encapsulation efficacy. The layered structure visible on atomic force micrographs was confirmed by nuclear magnetic resonance. Obtained formulations were desirably stable, with small particle size (<100 nm), and high encapsulation efficacy (>99 %). Lecithin was partially fluid and most probably located in the outer shell of the particle, together with DK-I-60-3. While the hydrophobic part of polysorbate 80 was completely immobilized, its hydrophilic part was free in the aqueous phase. In oral neuropharmacokinetic study in rats, an around 1.5-fold increase of area under the curve with LNP compared to NC was noticed both in brain and plasma. In bioavailability study, F value of LNP (34.7 ± 12.4 %) was 1.4-fold higher than of NC (24.5 ± 7.8 %); however, this difference did not reach statistical significance. Therefore, employment of LNP platform in preclinical formulation of DK-I-60-3 imparted an incremental improvement of its physicochemical as well as pharmacokinetic behavior.
PB  - Elsevier B.V.
T2  - International Journal of Pharmaceutics
T1  - High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances
VL  - 633
DO  - 10.1016/j.ijpharm.2023.122613
ER  - 

@article{
author = "Mitrović, Jelena and Divović-Matović, Branka and Knutson, Daniel E. and Petković, Miloš and Đorović, Đorđe and Ranđelović, Danijela V. and Dobričić, Vladimir and Đoković, Jelena and Lunter, Dominique J. and Cook, James M. and Savić, Miroslav and Savić, Snežana",
year = "2023",
abstract = "Preclinical development of deuterated pyrazoloquinolinone ligands, promising drug candidates for various neuropsychiatric disorders, was hindered by unusually low solubility in water and oils. DK-I-60-3 (7-methoxy-d3- 2-(4-methoxy-d3-phenyl)-2,5-dihydro-3Hpyrazolo[4,3-c]quinolin-3-one) is one of such pyrazoloquinolinones, and we recently reported about increased oral bioavailability of its nanocrystal formulation (NC). Lipid nano- particles (LNP) with a high concentration of lecithin, which enhances loading capacity of the lipid matrix, may give rise to further improvement. After preformulation studies by differential scanning calorimetry and polarized light microscopy, LNP were prepared by the hot high pressure homogenization, and characterized in terms of particle size, morphology, and encapsulation efficacy. The layered structure visible on atomic force micrographs was confirmed by nuclear magnetic resonance. Obtained formulations were desirably stable, with small particle size (<100 nm), and high encapsulation efficacy (>99 %). Lecithin was partially fluid and most probably located in the outer shell of the particle, together with DK-I-60-3. While the hydrophobic part of polysorbate 80 was completely immobilized, its hydrophilic part was free in the aqueous phase. In oral neuropharmacokinetic study in rats, an around 1.5-fold increase of area under the curve with LNP compared to NC was noticed both in brain and plasma. In bioavailability study, F value of LNP (34.7 ± 12.4 %) was 1.4-fold higher than of NC (24.5 ± 7.8 %); however, this difference did not reach statistical significance. Therefore, employment of LNP platform in preclinical formulation of DK-I-60-3 imparted an incremental improvement of its physicochemical as well as pharmacokinetic behavior.",
publisher = "Elsevier B.V.",
journal = "International Journal of Pharmaceutics",
title = "High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances",
volume = "633",
doi = "10.1016/j.ijpharm.2023.122613"
}

Mitrović, J., Divović-Matović, B., Knutson, D. E., Petković, M., Đorović, Đ., Ranđelović, D. V., Dobričić, V., Đoković, J., Lunter, D. J., Cook, J. M., Savić, M.,& Savić, S.. (2023). High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances. in International Journal of Pharmaceutics
Elsevier B.V.., 633.
https://doi.org/10.1016/j.ijpharm.2023.122613

Mitrović J, Divović-Matović B, Knutson DE, Petković M, Đorović Đ, Ranđelović DV, Dobričić V, Đoković J, Lunter DJ, Cook JM, Savić M, Savić S. High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances. in International Journal of Pharmaceutics. 2023;633.
doi:10.1016/j.ijpharm.2023.122613 .

Mitrović, Jelena, Divović-Matović, Branka, Knutson, Daniel E., Petković, Miloš, Đorović, Đorđe, Ranđelović, Danijela V., Dobričić, Vladimir, Đoković, Jelena, Lunter, Dominique J., Cook, James M., Savić, Miroslav, Savić, Snežana, "High amount of lecithin facilitates oral delivery of a poorly soluble pyrazoloquinolinone ligand formulated in lipid nanoparticles: Physicochemical, structural and pharmacokinetic performances" in International Journal of Pharmaceutics, 633 (2023),
https://doi.org/10.1016/j.ijpharm.2023.122613 . .

TY  - CONF
AU  - Ružić, Dušan
AU  - Petković, Miloš
AU  - Đoković, Nemanja
AU  - Santibanez, Juan
AU  - Pavić, Aleksandar
AU  - Ganesan, A.
AU  - Srdić Rajić, Tatjana
AU  - Nikolić, Katarina
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5074
AB  - Triple-negative breast cancer (TNBC) is an aggressive form of breast cancer that has poor survival rates due to the absence of specific molecular markers such as estrogen receptor (ER), progesterone receptor (PR), and human epidermal growth factor receptor 2 (HER2). In the era of precision oncology, it is recognized that an imbalance in post-translational modifications of histones, such as histone lysine acetylation and deacetylation, is closely linked to tumor initiation and progression. Two groups of enzymes control the reversible nature of histone post-translational acetylation: histone acetyltransferases (HATs) and histone deacetylases (HDACs). Isoform-specific targeting of HDACs is considered a rational strategy to develop safe anticancer therapeutics compared to non-selective HDAC inhibitors. However, non-selective HDAC inhibitors have been more extensively studied in clinical trials. This work presents the design and discovery of potent HDAC inhibitors that selectively target HDAC6 isozyme, using 1-benzhydryl piperazine as a surface recognition group with different hydrocarbon linkers. Through in vitro screening, two HDAC6-selective inhibitors with nanomolar IC50 values and two non-selective HDAC inhibitors were identified. Structure-based molecular modelling was utilized to investigate the impact of linker chemistry on the potency of synthesized inhibitors against HDAC6. The anti-cancer, anti-migratory, and anti-invasive activities of these compounds were evaluated using breast cancer cell lines (MDA-MB-231 and MCF-7). Experiments on a zebrafish MDA-MB-231 xenograft model demonstrated that a novel non-selective HDAC inhibitor (8b) with a seven-carbon-atom linker exhibited potent effects against tumor growth, metastasis, and angiogenesis at low micromolar concentrations.
PB  - Serbian Association on for Cancer Research Belgrade, Serbia
C3  - Oncology
Insights
T1  - Discovery of novel HDAC inhibitors for therapy of triple-negative breast cancer – preclinical study
VL  - 1
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5074
ER  - 

@conference{
author = "Ružić, Dušan and Petković, Miloš and Đoković, Nemanja and Santibanez, Juan and Pavić, Aleksandar and Ganesan, A. and Srdić Rajić, Tatjana and Nikolić, Katarina",
year = "2023",
abstract = "Triple-negative breast cancer (TNBC) is an aggressive form of breast cancer that has poor survival rates due to the absence of specific molecular markers such as estrogen receptor (ER), progesterone receptor (PR), and human epidermal growth factor receptor 2 (HER2). In the era of precision oncology, it is recognized that an imbalance in post-translational modifications of histones, such as histone lysine acetylation and deacetylation, is closely linked to tumor initiation and progression. Two groups of enzymes control the reversible nature of histone post-translational acetylation: histone acetyltransferases (HATs) and histone deacetylases (HDACs). Isoform-specific targeting of HDACs is considered a rational strategy to develop safe anticancer therapeutics compared to non-selective HDAC inhibitors. However, non-selective HDAC inhibitors have been more extensively studied in clinical trials. This work presents the design and discovery of potent HDAC inhibitors that selectively target HDAC6 isozyme, using 1-benzhydryl piperazine as a surface recognition group with different hydrocarbon linkers. Through in vitro screening, two HDAC6-selective inhibitors with nanomolar IC50 values and two non-selective HDAC inhibitors were identified. Structure-based molecular modelling was utilized to investigate the impact of linker chemistry on the potency of synthesized inhibitors against HDAC6. The anti-cancer, anti-migratory, and anti-invasive activities of these compounds were evaluated using breast cancer cell lines (MDA-MB-231 and MCF-7). Experiments on a zebrafish MDA-MB-231 xenograft model demonstrated that a novel non-selective HDAC inhibitor (8b) with a seven-carbon-atom linker exhibited potent effects against tumor growth, metastasis, and angiogenesis at low micromolar concentrations.",
publisher = "Serbian Association on for Cancer Research Belgrade, Serbia",
journal = "Oncology
Insights",
title = "Discovery of novel HDAC inhibitors for therapy of triple-negative breast cancer – preclinical study",
volume = "1",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5074"
}

Ružić, D., Petković, M., Đoković, N., Santibanez, J., Pavić, A., Ganesan, A., Srdić Rajić, T.,& Nikolić, K.. (2023). Discovery of novel HDAC inhibitors for therapy of triple-negative breast cancer – preclinical study. in Oncology
Insights
Serbian Association on for Cancer Research Belgrade, Serbia., 1.
https://hdl.handle.net/21.15107/rcub_farfar_5074

Ružić D, Petković M, Đoković N, Santibanez J, Pavić A, Ganesan A, Srdić Rajić T, Nikolić K. Discovery of novel HDAC inhibitors for therapy of triple-negative breast cancer – preclinical study. in Oncology
Insights. 2023;1.
https://hdl.handle.net/21.15107/rcub_farfar_5074 .

Ružić, Dušan, Petković, Miloš, Đoković, Nemanja, Santibanez, Juan, Pavić, Aleksandar, Ganesan, A., Srdić Rajić, Tatjana, Nikolić, Katarina, "Discovery of novel HDAC inhibitors for therapy of triple-negative breast cancer – preclinical study" in Oncology
Insights, 1 (2023),
https://hdl.handle.net/21.15107/rcub_farfar_5074 .

TY  - CONF
AU  - Beljkaš, Milan
AU  - Petković, Miloš
AU  - Nikolić, Katarina
AU  - Oljačić, Slavica
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5005
AB  - Histone deacetylases (HDACs) belong to a family of epigenetic enzymes that has 18 different
isoforms and play an important role in the development and progression of various tumors.
To date, five histone deacetylase inhibitors have been approved by the FDA, and are used
to treat multiple myeloma, cutaneous T-cell lymphoma, peripheral T-cell lymphoma, and
breast cancer (estrogen and/or progesterone positive) [1]. All of them are non-selective.
Therefore, their safety profile is poor and their efficacy is low in single therapy. One of our
previous research projects demonstrated the synergistic effect of HDAC inhibitors and
inhibitors of Rho-associated protein kinases (ROCK) in the treatment of pancreatic ductal
adenocarcinoma (PDAC) [2]. This finding led us to design of the dual HDAC/ROCK inhibitors
with potential effects on PDAC by using structure-based molecular docking method.
Molecular docking study was performed using GOLD software. The crystal structures of
ROCK1 (PDB: 6E9W), ROCK2 (PDB: 7JNT), HDAC1 (PDB: 5ICN), and HDAC6 (PDB: 5EDU)
enzymes were downloaded from the Protein Data Bank (PDB). The enzymes were prepared
for docking study using the online software Play Molecule-ProteinPrepare. The structures
of the ROCK1, ROCK2, HDAC1 and HDAC6 inhibitors with their pIC50 values were obtained
from the ChEMBL database. The dominant microspecies of all compounds at physiological
pH were selected by Marvin Sketch Sketch 6.1.0 program and their further geometrical
optimization were performed using the PM3 semi-empirical method and the Hartree-Fock
method with 3-21G basis set.
The virtual docking procedures for all four enzymes were validated and the calculated RMSD
values were below 2Å. The critical parts of the structures that establish the interactions
crucial for the inhibition of HDAC1, HDAC6, ROCK1, and ROCK2 were identified. Based on
the obtained resultsdual HDAC/ROCK inhibitors were designed and evaluated by validated
docking procedures and in silico ADMET profiling.
Taking into account all these findings, the most active compounds are selected and will be
further synthesized and evaluated using in vitro enzyme and cell tests.
PB  - International Association of Physical Chemists
C3  - 10th IAPC Meeting Tenth World Conference on Physico-Chemical Methods in Drug Discovery & Sixth World Conference on ADMET and DMPK Belgrade, Serbia, September 4-6
T1  - Virtual docking and design of novel Histone deacetylase and Rho- associated protein kinases dual inhibitors (HDAC/ROCKs)
SP  - 46
EP  - 46
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5005
ER  - 

@conference{
author = "Beljkaš, Milan and Petković, Miloš and Nikolić, Katarina and Oljačić, Slavica",
year = "2023",
abstract = "Histone deacetylases (HDACs) belong to a family of epigenetic enzymes that has 18 different
isoforms and play an important role in the development and progression of various tumors.
To date, five histone deacetylase inhibitors have been approved by the FDA, and are used
to treat multiple myeloma, cutaneous T-cell lymphoma, peripheral T-cell lymphoma, and
breast cancer (estrogen and/or progesterone positive) [1]. All of them are non-selective.
Therefore, their safety profile is poor and their efficacy is low in single therapy. One of our
previous research projects demonstrated the synergistic effect of HDAC inhibitors and
inhibitors of Rho-associated protein kinases (ROCK) in the treatment of pancreatic ductal
adenocarcinoma (PDAC) [2]. This finding led us to design of the dual HDAC/ROCK inhibitors
with potential effects on PDAC by using structure-based molecular docking method.
Molecular docking study was performed using GOLD software. The crystal structures of
ROCK1 (PDB: 6E9W), ROCK2 (PDB: 7JNT), HDAC1 (PDB: 5ICN), and HDAC6 (PDB: 5EDU)
enzymes were downloaded from the Protein Data Bank (PDB). The enzymes were prepared
for docking study using the online software Play Molecule-ProteinPrepare. The structures
of the ROCK1, ROCK2, HDAC1 and HDAC6 inhibitors with their pIC50 values were obtained
from the ChEMBL database. The dominant microspecies of all compounds at physiological
pH were selected by Marvin Sketch Sketch 6.1.0 program and their further geometrical
optimization were performed using the PM3 semi-empirical method and the Hartree-Fock
method with 3-21G basis set.
The virtual docking procedures for all four enzymes were validated and the calculated RMSD
values were below 2Å. The critical parts of the structures that establish the interactions
crucial for the inhibition of HDAC1, HDAC6, ROCK1, and ROCK2 were identified. Based on
the obtained resultsdual HDAC/ROCK inhibitors were designed and evaluated by validated
docking procedures and in silico ADMET profiling.
Taking into account all these findings, the most active compounds are selected and will be
further synthesized and evaluated using in vitro enzyme and cell tests.",
publisher = "International Association of Physical Chemists",
journal = "10th IAPC Meeting Tenth World Conference on Physico-Chemical Methods in Drug Discovery & Sixth World Conference on ADMET and DMPK Belgrade, Serbia, September 4-6",
title = "Virtual docking and design of novel Histone deacetylase and Rho- associated protein kinases dual inhibitors (HDAC/ROCKs)",
pages = "46-46",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5005"
}

Beljkaš, M., Petković, M., Nikolić, K.,& Oljačić, S.. (2023). Virtual docking and design of novel Histone deacetylase and Rho- associated protein kinases dual inhibitors (HDAC/ROCKs). in 10th IAPC Meeting Tenth World Conference on Physico-Chemical Methods in Drug Discovery & Sixth World Conference on ADMET and DMPK Belgrade, Serbia, September 4-6
International Association of Physical Chemists., 46-46.
https://hdl.handle.net/21.15107/rcub_farfar_5005

Beljkaš M, Petković M, Nikolić K, Oljačić S. Virtual docking and design of novel Histone deacetylase and Rho- associated protein kinases dual inhibitors (HDAC/ROCKs). in 10th IAPC Meeting Tenth World Conference on Physico-Chemical Methods in Drug Discovery & Sixth World Conference on ADMET and DMPK Belgrade, Serbia, September 4-6. 2023;:46-46.
https://hdl.handle.net/21.15107/rcub_farfar_5005 .

Beljkaš, Milan, Petković, Miloš, Nikolić, Katarina, Oljačić, Slavica, "Virtual docking and design of novel Histone deacetylase and Rho- associated protein kinases dual inhibitors (HDAC/ROCKs)" in 10th IAPC Meeting Tenth World Conference on Physico-Chemical Methods in Drug Discovery & Sixth World Conference on ADMET and DMPK Belgrade, Serbia, September 4-6 (2023):46-46,
https://hdl.handle.net/21.15107/rcub_farfar_5005 .

TY  - JOUR
AU  - Milutinović, Violeta
AU  - Petrović, Predrag
AU  - Petković, Miloš
AU  - Klaus, Anita
AU  - Ušjak, Ljuboš
AU  - Niketić, Marjan
AU  - Petrović, Silvana
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5180
AB  - The composition and anticholinesterase activity of the dried MeOH extracts of Hieracium scheppigianum and H. naegelianum underground parts (rhizomes and roots), as well as the anticholinesterase activity of the dried, previously chemically characterised MeOH extracts of the flowering aerial parts of these two and 26 other Hieracium species in the strict sense (s. str.), were investigated. Furthermore, the anticholinesterase activity of 12 selected secondary metabolites of these extracts was evaluated. Using semi-preparative LC-MS, five caffeoylquinic acids and the sesquiterpene lactone crepiside E were isolated from H. scheppigianum underground parts extract. All these compounds were also identified in the underground parts extract of H. naegelianum. Quantitative LC-MS analysis showed that the analysed underground parts extracts were rich in both caffeoylquinic acids (139.77 and 156.62 mg/g of extract, respectively) and crepiside E (126.88 and 116.58 mg/g). In the Ellman method, the tested extracts showed an interesting anti-AChE and/or anti-BChE activity (IC50=0.56–1.58 mg/mL), which can be explained, at least partially, by the presence of some of their constituents. Among the metabolites tested, the best activity was revealed for the flavonoids apigenin, luteolin and diosmetin, and the sesquiterpene lactone 8-epiixerisamine A (IC50=68.09–299.37 μM).
PB  - John Wiley and Sons Inc
T2  - Chemistry and Biodiversity
T1  - Investigation of Anticholinesterase Activity of Chemically Characterised Hieracium s. str. Methanol Extracts and Their Selected Metabolites
VL  - 20
IS  - 11
SP  - e202301044
DO  - 10.1002/cbdv.202301044
ER  - 

@article{
author = "Milutinović, Violeta and Petrović, Predrag and Petković, Miloš and Klaus, Anita and Ušjak, Ljuboš and Niketić, Marjan and Petrović, Silvana",
year = "2023",
abstract = "The composition and anticholinesterase activity of the dried MeOH extracts of Hieracium scheppigianum and H. naegelianum underground parts (rhizomes and roots), as well as the anticholinesterase activity of the dried, previously chemically characterised MeOH extracts of the flowering aerial parts of these two and 26 other Hieracium species in the strict sense (s. str.), were investigated. Furthermore, the anticholinesterase activity of 12 selected secondary metabolites of these extracts was evaluated. Using semi-preparative LC-MS, five caffeoylquinic acids and the sesquiterpene lactone crepiside E were isolated from H. scheppigianum underground parts extract. All these compounds were also identified in the underground parts extract of H. naegelianum. Quantitative LC-MS analysis showed that the analysed underground parts extracts were rich in both caffeoylquinic acids (139.77 and 156.62 mg/g of extract, respectively) and crepiside E (126.88 and 116.58 mg/g). In the Ellman method, the tested extracts showed an interesting anti-AChE and/or anti-BChE activity (IC50=0.56–1.58 mg/mL), which can be explained, at least partially, by the presence of some of their constituents. Among the metabolites tested, the best activity was revealed for the flavonoids apigenin, luteolin and diosmetin, and the sesquiterpene lactone 8-epiixerisamine A (IC50=68.09–299.37 μM).",
publisher = "John Wiley and Sons Inc",
journal = "Chemistry and Biodiversity",
title = "Investigation of Anticholinesterase Activity of Chemically Characterised Hieracium s. str. Methanol Extracts and Their Selected Metabolites",
volume = "20",
number = "11",
pages = "e202301044",
doi = "10.1002/cbdv.202301044"
}

Milutinović, V., Petrović, P., Petković, M., Klaus, A., Ušjak, L., Niketić, M.,& Petrović, S.. (2023). Investigation of Anticholinesterase Activity of Chemically Characterised Hieracium s. str. Methanol Extracts and Their Selected Metabolites. in Chemistry and Biodiversity
John Wiley and Sons Inc., 20(11), e202301044.
https://doi.org/10.1002/cbdv.202301044

Milutinović V, Petrović P, Petković M, Klaus A, Ušjak L, Niketić M, Petrović S. Investigation of Anticholinesterase Activity of Chemically Characterised Hieracium s. str. Methanol Extracts and Their Selected Metabolites. in Chemistry and Biodiversity. 2023;20(11):e202301044.
doi:10.1002/cbdv.202301044 .

Milutinović, Violeta, Petrović, Predrag, Petković, Miloš, Klaus, Anita, Ušjak, Ljuboš, Niketić, Marjan, Petrović, Silvana, "Investigation of Anticholinesterase Activity of Chemically Characterised Hieracium s. str. Methanol Extracts and Their Selected Metabolites" in Chemistry and Biodiversity, 20, no. 11 (2023):e202301044,
https://doi.org/10.1002/cbdv.202301044 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Maslak, Veselin
AU  - Rakić, Srđan
AU  - Rodić, Marko
AU  - Vlahović, Filip
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4953
AB  - Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.
PB  - John Wiley and Sons Inc
T2  - Advanced Synthesis and Catalysis
T1  - Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis
DO  - 10.1002/adsc.202300301
ER  - 

@article{
author = "Jovanović, Miloš and Jovanović, Predrag and Tasić, Gordana and Simić, Milena and Maslak, Veselin and Rakić, Srđan and Rodić, Marko and Vlahović, Filip and Petković, Miloš and Savić, Vladimir",
year = "2023",
abstract = "Enallenylamides have been utilized for the synthesis of heterobicycle[4.2.0]octane derivatives via Ir/hν promoted [2+2] cycloaddition reaction. The reaction specifically targets the distal double bond of the allene moiety, and results in the exclusive formation of the trans product. The process is conducted at room temperature and under an inert atmosphere. An extensive study on the substituent propensities during the cycloaddition step revealed variable effects. Electron-withdrawing groups conjugated with the double bond participating in the cycloaddition either hindered the process or reduced its yield. Conversely, electron-donating substituents enhanced the efficiency, resulting in product yields ranging from 60% to 88%. Our study also demonstrated the influence of protecting groups on the reaction pathway.",
publisher = "John Wiley and Sons Inc",
journal = "Advanced Synthesis and Catalysis",
title = "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis",
doi = "10.1002/adsc.202300301"
}

Jovanović, M., Jovanović, P., Tasić, G., Simić, M., Maslak, V., Rakić, S., Rodić, M., Vlahović, F., Petković, M.,& Savić, V.. (2023). Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis
John Wiley and Sons Inc..
https://doi.org/10.1002/adsc.202300301

Jovanović M, Jovanović P, Tasić G, Simić M, Maslak V, Rakić S, Rodić M, Vlahović F, Petković M, Savić V. Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis. in Advanced Synthesis and Catalysis. 2023;.
doi:10.1002/adsc.202300301 .

Jovanović, Miloš, Jovanović, Predrag, Tasić, Gordana, Simić, Milena, Maslak, Veselin, Rakić, Srđan, Rodić, Marko, Vlahović, Filip, Petković, Miloš, Savić, Vladimir, "Regio- and Stereoselective, Intramolecular [2+2] Cycloaddition of Allenes, Promoted by Visible Light Photocatalysis" in Advanced Synthesis and Catalysis (2023),
https://doi.org/10.1002/adsc.202300301 . .

TY  - JOUR
AU  - Simić, Milena
AU  - Kotur-Stevuljević, Jelena
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Savić, Vladimir
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4934
AB  - Disruption of the redox balance in the body causes oxidative stress that can initiate many diseases. While antioxidants reduce the level of oxidiz- ing compounds in the medium, prooxidants promote the opposite process and have been used in therapies in particular those of cancer diseases. In this study, a series of azolyl lactones, were tested in human serum as a biological matrix and the obtained values of their oxy scores (OS) were compared. The antioxid- ative properties of these compounds were also tested under conditions of ind- uced oxidative stress using an external prooxidant, t-butylhydroperoxide. The results showed that the sulphur analogue 4-azolyl coumarin 5 has the best anti- oxidant properties (OS –2.2), while the halogenated derivatives of pyrazolyl- coumarin 7 and 8 act as prooxidants, but successfully resist oxidative stress (OS 2.7 and 2.0, respectively). Related phthalides and isocoumarins showed prooxidative properties, but azolyl isocoumarins 10 and 11 show the strongest resistance to oxidative stress, reflected in their negative oxy score value (OS –2.1 and –1.1, respectively). The results demonstrated that combining two pharmacophores with known redox properties can produce potent compounds in both directions, with the antioxidative and the prooxidative characteristics.
AB  - Поремећај редокс баланса у организму може узроковати оксидативни стрес, који је окидач за настанак многих болести. Антиоксиданси снижавају ниво оксидујућих једи- њења у медијуму у коме се налазе, док прооксиданси делују супротно и као такви могу наћи примену у терапији канцера. У овом истраживању, испитиване су антиоксидативне и прооксидативне особине серије азолил-лактона у хуманом серуму као биолошком матриксу. Антиоксидативне особине су представљене помоћу окси скорова (ОS), а испи- тивано је и понашање ових једињења у условима индукованог оксидативног стреса нас- талог додатком терц-бутил-хидропероксида као спољног прооксиданса. Резултати су показали да сумпорни дериват, 4-бензимидазолил кумарин 5 има најизраженије анти- оксидативне особине (ОS –2,2), док халогеновани деривати пиразолил-кумарина 7 и 8 реагују као прооксиданси (ОS 2,7 и 2,0). Утицају додатог прооксиданса се најбоље опиру једињења 7 и 8. Испитивани деривати изокумарина и фталида такође показују проокси- дативне особине, док се оксидативном стресу најбоље опиру азолил-изокумарини (ОS < 0).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - In vitro study of redox properties of azolyl-lactones in human serum
T1  - In vitro студија редокс особина азолил-лактона у хуманом серуму
VL  - 88
IS  - 6
SP  - 589
EP  - 601
DO  - 10.2298/JSC221221017S
ER  - 

@article{
author = "Simić, Milena and Kotur-Stevuljević, Jelena and Jovanović, Predrag and Petković, Miloš and Jovanović, Miloš and Tasić, Gordana and Savić, Vladimir",
year = "2023",
abstract = "Disruption of the redox balance in the body causes oxidative stress that can initiate many diseases. While antioxidants reduce the level of oxidiz- ing compounds in the medium, prooxidants promote the opposite process and have been used in therapies in particular those of cancer diseases. In this study, a series of azolyl lactones, were tested in human serum as a biological matrix and the obtained values of their oxy scores (OS) were compared. The antioxid- ative properties of these compounds were also tested under conditions of ind- uced oxidative stress using an external prooxidant, t-butylhydroperoxide. The results showed that the sulphur analogue 4-azolyl coumarin 5 has the best anti- oxidant properties (OS –2.2), while the halogenated derivatives of pyrazolyl- coumarin 7 and 8 act as prooxidants, but successfully resist oxidative stress (OS 2.7 and 2.0, respectively). Related phthalides and isocoumarins showed prooxidative properties, but azolyl isocoumarins 10 and 11 show the strongest resistance to oxidative stress, reflected in their negative oxy score value (OS –2.1 and –1.1, respectively). The results demonstrated that combining two pharmacophores with known redox properties can produce potent compounds in both directions, with the antioxidative and the prooxidative characteristics., Поремећај редокс баланса у организму може узроковати оксидативни стрес, који је окидач за настанак многих болести. Антиоксиданси снижавају ниво оксидујућих једи- њења у медијуму у коме се налазе, док прооксиданси делују супротно и као такви могу наћи примену у терапији канцера. У овом истраживању, испитиване су антиоксидативне и прооксидативне особине серије азолил-лактона у хуманом серуму као биолошком матриксу. Антиоксидативне особине су представљене помоћу окси скорова (ОS), а испи- тивано је и понашање ових једињења у условима индукованог оксидативног стреса нас- талог додатком терц-бутил-хидропероксида као спољног прооксиданса. Резултати су показали да сумпорни дериват, 4-бензимидазолил кумарин 5 има најизраженије анти- оксидативне особине (ОS –2,2), док халогеновани деривати пиразолил-кумарина 7 и 8 реагују као прооксиданси (ОS 2,7 и 2,0). Утицају додатог прооксиданса се најбоље опиру једињења 7 и 8. Испитивани деривати изокумарина и фталида такође показују проокси- дативне особине, док се оксидативном стресу најбоље опиру азолил-изокумарини (ОS < 0).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "In vitro study of redox properties of azolyl-lactones in human serum, In vitro студија редокс особина азолил-лактона у хуманом серуму",
volume = "88",
number = "6",
pages = "589-601",
doi = "10.2298/JSC221221017S"
}

Simić, M., Kotur-Stevuljević, J., Jovanović, P., Petković, M., Jovanović, M., Tasić, G.,& Savić, V.. (2023). In vitro study of redox properties of azolyl-lactones in human serum. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 88(6), 589-601.
https://doi.org/10.2298/JSC221221017S

Simić M, Kotur-Stevuljević J, Jovanović P, Petković M, Jovanović M, Tasić G, Savić V. In vitro study of redox properties of azolyl-lactones in human serum. in Journal of the Serbian Chemical Society. 2023;88(6):589-601.
doi:10.2298/JSC221221017S .

Simić, Milena, Kotur-Stevuljević, Jelena, Jovanović, Predrag, Petković, Miloš, Jovanović, Miloš, Tasić, Gordana, Savić, Vladimir, "In vitro study of redox properties of azolyl-lactones in human serum" in Journal of the Serbian Chemical Society, 88, no. 6 (2023):589-601,
https://doi.org/10.2298/JSC221221017S . .

TY  - CONF
AU  - Kukić-Marković, Jelena
AU  - Petković, Miloš
AU  - Niketić, Marjan
AU  - Petrović, Silvana
PY  - 2023
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4987
AB  - Stachys annua (L.) L. (annual yellow-woundwort) is an arrable weed and melliferous archaeophyte, with the native range in Europe to Siberia and Iran [1]. The aim of this work is to implement simple chromatographic technique for isolation of flavonoids from crude methanol extract of S. annua aerial flowering parts (herb).  
Plant material collected in NW Serbia (Mt Sokolske planine) was air-dried, powdered, and then extracted by bimaceration with chloroform and methanol. Dry methanol extract of S. annua herb was applied on preparative TLC plates of silica gel. After developing of chromatogram in methylene chloride:methanol:water (40:10:1, V/V/V), and spraying with NP/PEG reagent, in ultraviolet light at 365 nm three clearly separated fluorescence-quenching zones were observed. Zones were eluted with mixture of methylene chloride and methanol (1:1, V/V), and using LC-MS analysis one dominant compound was detected in each of these fractions. According to their UV, MS and 1H-NMR spectral data, as well as using flavonoids previously isolated from S. alpina subsp. dinarica [2], these compounds (1-3) were identified as 8-hydroxyflavone glycosides, namely: isoscutellarein-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 1), 3'-hydroxy-4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 2) and 4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 3).
It could be concluded that the developed preparative TLC method is suitable for rapid isolation of the mentioned flavonoid biosides from the crude methanol extract of S. annua without prior fractionation by other chromatographic techniques.
C3  - 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts
T1  - Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)
SP  - 194
EP  - 195
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4987
ER  - 

@conference{
author = "Kukić-Marković, Jelena and Petković, Miloš and Niketić, Marjan and Petrović, Silvana",
year = "2023",
abstract = "Stachys annua (L.) L. (annual yellow-woundwort) is an arrable weed and melliferous archaeophyte, with the native range in Europe to Siberia and Iran [1]. The aim of this work is to implement simple chromatographic technique for isolation of flavonoids from crude methanol extract of S. annua aerial flowering parts (herb).  
Plant material collected in NW Serbia (Mt Sokolske planine) was air-dried, powdered, and then extracted by bimaceration with chloroform and methanol. Dry methanol extract of S. annua herb was applied on preparative TLC plates of silica gel. After developing of chromatogram in methylene chloride:methanol:water (40:10:1, V/V/V), and spraying with NP/PEG reagent, in ultraviolet light at 365 nm three clearly separated fluorescence-quenching zones were observed. Zones were eluted with mixture of methylene chloride and methanol (1:1, V/V), and using LC-MS analysis one dominant compound was detected in each of these fractions. According to their UV, MS and 1H-NMR spectral data, as well as using flavonoids previously isolated from S. alpina subsp. dinarica [2], these compounds (1-3) were identified as 8-hydroxyflavone glycosides, namely: isoscutellarein-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 1), 3'-hydroxy-4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 2) and 4'-O-methylisoscutellareine-7-O-[6'''-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (compound 3).
It could be concluded that the developed preparative TLC method is suitable for rapid isolation of the mentioned flavonoid biosides from the crude methanol extract of S. annua without prior fractionation by other chromatographic techniques.",
journal = "5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts",
title = "Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)",
pages = "194-195",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4987"
}

Kukić-Marković, J., Petković, M., Niketić, M.,& Petrović, S.. (2023). Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae). in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts, 194-195.
https://hdl.handle.net/21.15107/rcub_farfar_4987

Kukić-Marković J, Petković M, Niketić M, Petrović S. Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae). in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts. 2023;:194-195.
https://hdl.handle.net/21.15107/rcub_farfar_4987 .

Kukić-Marković, Jelena, Petković, Miloš, Niketić, Marjan, Petrović, Silvana, "Structural elucidation of flavonoids isolated from aerial parts of Stachys annua (L.) L. (Lamiaceae)" in 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf - ICNPU-2023 Book of Abstracts (2023):194-195,
https://hdl.handle.net/21.15107/rcub_farfar_4987 .

TY  - CONF
AU  - Mitrović, Jelena
AU  - Petković, Miloš
AU  - Ranđelović, Danijela
AU  - Đoković, Jelena
AU  - Knutson, Daniel
AU  - Cook, James
AU  - Savić, Vladimir
AU  - Savić, Miroslav
AU  - Savić, Snežana
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4097
AB  - Lipid nanoparticles are being intensively investigated for
the formulation of the drugs with poor solubility substances
(1). They represent colloid dispersions of the particles with
lipid matrix that is solid at room and body temperature.
Because of the low capacity of triglycerides for the drug
substances incorporation, alternatively, high amounts of
lecithin could be added to increase the solubilization (2).
This was used for the incorporation of DK-I-60-3 (7-
methoxy-d3-2-(4-methoxyd3-phenyl)-2,5-dihydro-
3Hpyrazolo[4,3-c]quinolin-3-one), novel deuterated
pyrazoloquinolinone ligand, with very low solubility in
water as well as in oils (3,4). However, because of
amphiphilic nature of lecithin, its localization within
nanoparticles should be analyzed, especially with respect
to stability, drug loading capacity and drug localization,
because it may additionally influence the drug release
mechanism (2).
C3  - 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands
T1  - Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4097
ER  - 

@conference{
author = "Mitrović, Jelena and Petković, Miloš and Ranđelović, Danijela and Đoković, Jelena and Knutson, Daniel and Cook, James and Savić, Vladimir and Savić, Miroslav and Savić, Snežana",
year = "2022",
abstract = "Lipid nanoparticles are being intensively investigated for
the formulation of the drugs with poor solubility substances
(1). They represent colloid dispersions of the particles with
lipid matrix that is solid at room and body temperature.
Because of the low capacity of triglycerides for the drug
substances incorporation, alternatively, high amounts of
lecithin could be added to increase the solubilization (2).
This was used for the incorporation of DK-I-60-3 (7-
methoxy-d3-2-(4-methoxyd3-phenyl)-2,5-dihydro-
3Hpyrazolo[4,3-c]quinolin-3-one), novel deuterated
pyrazoloquinolinone ligand, with very low solubility in
water as well as in oils (3,4). However, because of
amphiphilic nature of lecithin, its localization within
nanoparticles should be analyzed, especially with respect
to stability, drug loading capacity and drug localization,
because it may additionally influence the drug release
mechanism (2).",
journal = "13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands",
title = "Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4097"
}

Mitrović, J., Petković, M., Ranđelović, D., Đoković, J., Knutson, D., Cook, J., Savić, V., Savić, M.,& Savić, S.. (2022). Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3. in 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands.
https://hdl.handle.net/21.15107/rcub_farfar_4097

Mitrović J, Petković M, Ranđelović D, Đoković J, Knutson D, Cook J, Savić V, Savić M, Savić S. Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3. in 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands. 2022;.
https://hdl.handle.net/21.15107/rcub_farfar_4097 .

Mitrović, Jelena, Petković, Miloš, Ranđelović, Danijela, Đoković, Jelena, Knutson, Daniel, Cook, James, Savić, Vladimir, Savić, Miroslav, Savić, Snežana, "Physicochemical/structural investigation of lipid nanoparticles with high lecithin amounts loaded with patent protected pyrazoloquinolinone ligand DK-I-60-3" in 13th World meeting on pharmaceutics, biopharmaceutics and pharmaceutical technology, 28-31 March 2022, Rotterdam, Netherlands (2022),
https://hdl.handle.net/21.15107/rcub_farfar_4097 .

TY  - CONF
AU  - Čarapić, Marija
AU  - Petković, Miloš
AU  - Marković, Bojan
AU  - Popović-Nikolić, Marija
AU  - Agbaba, Danica
AU  - Nikolić, Katarina
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4684
AB  - Ziprasidone (ZIP) is the second generation antipsychotic drug with unique G-protein-coupled
(GPCR) receptor binding profile. It is a highly lipophilic and unstable compound. Our group
developed and validated the single liquid chromatographic (LC) system for simultaneous
determination of ZIP and its five main impurities (IMPs) and we modelled the Quantitative
Structure Retention Relationship (QSRR) of the additional ten compounds including unknown
detected degradant. One of two proposed structures were confirmed by UPLC-MS/MS study. The
further characterisation of unknown degradant was performed with NMR studies as un versatile
tool for characterisation of each compound and it is presented. Through several experiments which consists of investigation of chemical shitfs in NMR spectra of ZIP degradation products the
structure of unknown degradant was proposed and confirmed as in previous experiments.
PB  - Society of Physical Chemists of Serbia
C3  - PHYSICAL CHEMISTRY 2022, 16th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings)
T1  - Characterization of unknown degradant of ziprasidone with NMR spetroscopy
VL  - II
SP  - 601
EP  - 604
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4684
ER  - 

@conference{
author = "Čarapić, Marija and Petković, Miloš and Marković, Bojan and Popović-Nikolić, Marija and Agbaba, Danica and Nikolić, Katarina",
year = "2022",
abstract = "Ziprasidone (ZIP) is the second generation antipsychotic drug with unique G-protein-coupled
(GPCR) receptor binding profile. It is a highly lipophilic and unstable compound. Our group
developed and validated the single liquid chromatographic (LC) system for simultaneous
determination of ZIP and its five main impurities (IMPs) and we modelled the Quantitative
Structure Retention Relationship (QSRR) of the additional ten compounds including unknown
detected degradant. One of two proposed structures were confirmed by UPLC-MS/MS study. The
further characterisation of unknown degradant was performed with NMR studies as un versatile
tool for characterisation of each compound and it is presented. Through several experiments which consists of investigation of chemical shitfs in NMR spectra of ZIP degradation products the
structure of unknown degradant was proposed and confirmed as in previous experiments.",
publisher = "Society of Physical Chemists of Serbia",
journal = "PHYSICAL CHEMISTRY 2022, 16th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings)",
title = "Characterization of unknown degradant of ziprasidone with NMR spetroscopy",
volume = "II",
pages = "601-604",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4684"
}

Čarapić, M., Petković, M., Marković, B., Popović-Nikolić, M., Agbaba, D.,& Nikolić, K.. (2022). Characterization of unknown degradant of ziprasidone with NMR spetroscopy. in PHYSICAL CHEMISTRY 2022, 16th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings)
Society of Physical Chemists of Serbia., II, 601-604.
https://hdl.handle.net/21.15107/rcub_farfar_4684

Čarapić M, Petković M, Marković B, Popović-Nikolić M, Agbaba D, Nikolić K. Characterization of unknown degradant of ziprasidone with NMR spetroscopy. in PHYSICAL CHEMISTRY 2022, 16th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings). 2022;II:601-604.
https://hdl.handle.net/21.15107/rcub_farfar_4684 .

Čarapić, Marija, Petković, Miloš, Marković, Bojan, Popović-Nikolić, Marija, Agbaba, Danica, Nikolić, Katarina, "Characterization of unknown degradant of ziprasidone with NMR spetroscopy" in PHYSICAL CHEMISTRY 2022, 16th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings), II (2022):601-604,
https://hdl.handle.net/21.15107/rcub_farfar_4684 .

TY  - JOUR
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Jovanović, Predrag
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5380
AB  - Једињења која у структури садрже халогене су
доста распрострањена у природи и најчешће се могу
изоловати из морских организама. За разлику од бромованих и хлорованих деривата, природни производи који садрже органски везан флуор веома су ретки.
Флуорована органска једињења често имају изражену биолошку активност и примењују се у фармацији.
AB  - Halogenated compounds are very widespread in
nature. The most common sources of these natural
products are marine organisms. Unlike brominated and
chlorinated derivatives, natural compounds containing
carbon-fluorine bound are very rare. Extensive study of
this relatively small class of natural products provides
important information about their physiological activity
and application in drug synthesis. This paper presents
a brief overview of naturally occurring fluorinated
compounds.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Hemijski pregled
T1  - Флуоровани природни производи
T1  - Fluorinated natural products
VL  - 64
IS  - 3-4
SP  - 73
EP  - 79
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5380
ER  - 

@article{
author = "Simić, Milena and Petković, Miloš and Jovanović, Predrag",
year = "2022",
abstract = "Једињења која у структури садрже халогене су
доста распрострањена у природи и најчешће се могу
изоловати из морских организама. За разлику од бромованих и хлорованих деривата, природни производи који садрже органски везан флуор веома су ретки.
Флуорована органска једињења често имају изражену биолошку активност и примењују се у фармацији., Halogenated compounds are very widespread in
nature. The most common sources of these natural
products are marine organisms. Unlike brominated and
chlorinated derivatives, natural compounds containing
carbon-fluorine bound are very rare. Extensive study of
this relatively small class of natural products provides
important information about their physiological activity
and application in drug synthesis. This paper presents
a brief overview of naturally occurring fluorinated
compounds.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Hemijski pregled",
title = "Флуоровани природни производи, Fluorinated natural products",
volume = "64",
number = "3-4",
pages = "73-79",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5380"
}

Simić, M., Petković, M.,& Jovanović, P.. (2022). Флуоровани природни производи. in Hemijski pregled
Srpsko hemijsko društvo, Beograd., 64(3-4), 73-79.
https://hdl.handle.net/21.15107/rcub_farfar_5380

Simić M, Petković M, Jovanović P. Флуоровани природни производи. in Hemijski pregled. 2022;64(3-4):73-79.
https://hdl.handle.net/21.15107/rcub_farfar_5380 .

Simić, Milena, Petković, Miloš, Jovanović, Predrag, "Флуоровани природни производи" in Hemijski pregled, 64, no. 3-4 (2022):73-79,
https://hdl.handle.net/21.15107/rcub_farfar_5380 .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5379
AB  - Под органокатализом подразумева се употреба
малих органских молекула који катализују
органске трансформације. Термин органокатализа
први је употребио Дејвид Мекмилан (David
MacMillan) на почетку двадесет првог века, који
је био и зачетник интензивнијег истраживања
у овој области. ...
AB  - This paper discusses the basic structural
characteristics of proline catalysts, which have
found application in many synthetically useful
transformations with high degree of chemical and
stereochemical efficiency. Organocatalysts obtained by
modification of proline can be divided into six major
categories. This text lists some catalyst examples and
the reactions they catalyze.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Hemijski pregled
T1  - Пролински катализатори у органокатализи
T1  - Proline catalysts in organocatalysis
VL  - 63
IS  - 1
SP  - 17
EP  - 25
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5379
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena",
year = "2022",
abstract = "Под органокатализом подразумева се употреба
малих органских молекула који катализују
органске трансформације. Термин органокатализа
први је употребио Дејвид Мекмилан (David
MacMillan) на почетку двадесет првог века, који
је био и зачетник интензивнијег истраживања
у овој области. ..., This paper discusses the basic structural
characteristics of proline catalysts, which have
found application in many synthetically useful
transformations with high degree of chemical and
stereochemical efficiency. Organocatalysts obtained by
modification of proline can be divided into six major
categories. This text lists some catalyst examples and
the reactions they catalyze.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Hemijski pregled",
title = "Пролински катализатори у органокатализи, Proline catalysts in organocatalysis",
volume = "63",
number = "1",
pages = "17-25",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5379"
}

Jovanović, P., Petković, M.,& Simić, M.. (2022). Пролински катализатори у органокатализи. in Hemijski pregled
Srpsko hemijsko društvo, Beograd., 63(1), 17-25.
https://hdl.handle.net/21.15107/rcub_farfar_5379

Jovanović P, Petković M, Simić M. Пролински катализатори у органокатализи. in Hemijski pregled. 2022;63(1):17-25.
https://hdl.handle.net/21.15107/rcub_farfar_5379 .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, "Пролински катализатори у органокатализи" in Hemijski pregled, 63, no. 1 (2022):17-25,
https://hdl.handle.net/21.15107/rcub_farfar_5379 .

TY  - JOUR
AU  - Ružić, Dušan
AU  - Ellinger, Bernhard
AU  - Đoković, Nemanja
AU  - Santibanez, Juan
AU  - Gul, Sheraz
AU  - Beljkaš, Milan
AU  - Đurić, Ana
AU  - Ganesan, Arasu
AU  - Pavić, Aleksandar
AU  - Srdić-Rajić, Tatjana
AU  - Petković, Miloš
AU  - Nikolić, Katarina
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4368
AB  - Isoform-selective histone deacetylase (HDAC) inhibition is promoted as a rational strategy to develop safer anti-cancer drugs compared to non-selective HDAC inhibitors. Despite this presumed benefit, considerably more non-selective HDAC inhibitors have undergone clinical trials. In this report, we detail the design and discovery of potent HDAC inhibitors, with 1-benzhydryl piperazine as a surface recognition group, that differ in hydrocarbon linker. In vitro HDAC screening identified two selective HDAC6 inhibitors with nanomolar IC50 values, as well as two non-selective nanomolar HDAC inhibitors. Structure-based molecular modeling was employed to study the influence of linker chemistry of synthesized inhibitors on HDAC6 potency. The breast cancer cell lines (MDA-MB-231 and MCF-7) were used to evaluate compound-mediated in vitro anti-cancer, anti-migratory, and anti-invasive activities. Experiments on the zebrafish MDA-MB-231 xenograft model revealed that a novel non-selective HDAC inhibitor with a seven-carbon-atom linker exhibits potent anti-tumor, anti-metastatic, and anti-angiogenic effects when tested at low micromolar concentrations.
PB  - MDPI
T2  - Pharmaceutics
T1  - Discovery of 1-Benzhydryl-Piperazine-Based HDAC Inhibitors with Anti-Breast Cancer Activity: Synthesis, Molecular Modeling, In Vitro and In Vivo Biological Evaluation
VL  - 14
IS  - 12
DO  - 10.3390/pharmaceutics14122600
ER  - 

@article{
author = "Ružić, Dušan and Ellinger, Bernhard and Đoković, Nemanja and Santibanez, Juan and Gul, Sheraz and Beljkaš, Milan and Đurić, Ana and Ganesan, Arasu and Pavić, Aleksandar and Srdić-Rajić, Tatjana and Petković, Miloš and Nikolić, Katarina",
year = "2022",
abstract = "Isoform-selective histone deacetylase (HDAC) inhibition is promoted as a rational strategy to develop safer anti-cancer drugs compared to non-selective HDAC inhibitors. Despite this presumed benefit, considerably more non-selective HDAC inhibitors have undergone clinical trials. In this report, we detail the design and discovery of potent HDAC inhibitors, with 1-benzhydryl piperazine as a surface recognition group, that differ in hydrocarbon linker. In vitro HDAC screening identified two selective HDAC6 inhibitors with nanomolar IC50 values, as well as two non-selective nanomolar HDAC inhibitors. Structure-based molecular modeling was employed to study the influence of linker chemistry of synthesized inhibitors on HDAC6 potency. The breast cancer cell lines (MDA-MB-231 and MCF-7) were used to evaluate compound-mediated in vitro anti-cancer, anti-migratory, and anti-invasive activities. Experiments on the zebrafish MDA-MB-231 xenograft model revealed that a novel non-selective HDAC inhibitor with a seven-carbon-atom linker exhibits potent anti-tumor, anti-metastatic, and anti-angiogenic effects when tested at low micromolar concentrations.",
publisher = "MDPI",
journal = "Pharmaceutics",
title = "Discovery of 1-Benzhydryl-Piperazine-Based HDAC Inhibitors with Anti-Breast Cancer Activity: Synthesis, Molecular Modeling, In Vitro and In Vivo Biological Evaluation",
volume = "14",
number = "12",
doi = "10.3390/pharmaceutics14122600"
}

Ružić, D., Ellinger, B., Đoković, N., Santibanez, J., Gul, S., Beljkaš, M., Đurić, A., Ganesan, A., Pavić, A., Srdić-Rajić, T., Petković, M.,& Nikolić, K.. (2022). Discovery of 1-Benzhydryl-Piperazine-Based HDAC Inhibitors with Anti-Breast Cancer Activity: Synthesis, Molecular Modeling, In Vitro and In Vivo Biological Evaluation. in Pharmaceutics
MDPI., 14(12).
https://doi.org/10.3390/pharmaceutics14122600

Ružić D, Ellinger B, Đoković N, Santibanez J, Gul S, Beljkaš M, Đurić A, Ganesan A, Pavić A, Srdić-Rajić T, Petković M, Nikolić K. Discovery of 1-Benzhydryl-Piperazine-Based HDAC Inhibitors with Anti-Breast Cancer Activity: Synthesis, Molecular Modeling, In Vitro and In Vivo Biological Evaluation. in Pharmaceutics. 2022;14(12).
doi:10.3390/pharmaceutics14122600 .

Ružić, Dušan, Ellinger, Bernhard, Đoković, Nemanja, Santibanez, Juan, Gul, Sheraz, Beljkaš, Milan, Đurić, Ana, Ganesan, Arasu, Pavić, Aleksandar, Srdić-Rajić, Tatjana, Petković, Miloš, Nikolić, Katarina, "Discovery of 1-Benzhydryl-Piperazine-Based HDAC Inhibitors with Anti-Breast Cancer Activity: Synthesis, Molecular Modeling, In Vitro and In Vivo Biological Evaluation" in Pharmaceutics, 14, no. 12 (2022),
https://doi.org/10.3390/pharmaceutics14122600 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Tasić, Gordana
AU  - Maslak, Veselin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4175
AB  - A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1 mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.
PB  - Wiley Periodicals LLC
T2  - Journal of Heterocyclic Chemistry
T1  - Highly exo selective, photochemically promoted cyclization of iodoallene derivatives
VL  - 59
IS  - 8
SP  - 1435
EP  - 1440
DO  - 10.1002/jhet.4472
ER  - 

@article{
author = "Jovanović, Miloš and Simić, Milena and Petković, Miloš and Tasić, Gordana and Maslak, Veselin and Jovanović, Predrag and Savić, Vladimir",
year = "2022",
abstract = "A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1 mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.",
publisher = "Wiley Periodicals LLC",
journal = "Journal of Heterocyclic Chemistry",
title = "Highly exo selective, photochemically promoted cyclization of iodoallene derivatives",
volume = "59",
number = "8",
pages = "1435-1440",
doi = "10.1002/jhet.4472"
}

Jovanović, M., Simić, M., Petković, M., Tasić, G., Maslak, V., Jovanović, P.,& Savić, V.. (2022). Highly exo selective, photochemically promoted cyclization of iodoallene derivatives. in Journal of Heterocyclic Chemistry
Wiley Periodicals LLC., 59(8), 1435-1440.
https://doi.org/10.1002/jhet.4472

Jovanović M, Simić M, Petković M, Tasić G, Maslak V, Jovanović P, Savić V. Highly exo selective, photochemically promoted cyclization of iodoallene derivatives. in Journal of Heterocyclic Chemistry. 2022;59(8):1435-1440.
doi:10.1002/jhet.4472 .

Jovanović, Miloš, Simić, Milena, Petković, Miloš, Tasić, Gordana, Maslak, Veselin, Jovanović, Predrag, Savić, Vladimir, "Highly exo selective, photochemically promoted cyclization of iodoallene derivatives" in Journal of Heterocyclic Chemistry, 59, no. 8 (2022):1435-1440,
https://doi.org/10.1002/jhet.4472 . .

TY  - JOUR
AU  - Petković, Miloš
AU  - Jovanović, Miloš
AU  - Jovanović, Predrag
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Savić, Vladimir
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4720
AB  - Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields.
PB  - Georg Thieme Verlag
T2  - Synthesis
T1  - Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives
VL  - 54
IS  - 12
SP  - 2839
EP  - 2848
DO  - 10.1055/a-1758-6312
ER  - 

@article{
author = "Petković, Miloš and Jovanović, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Savić, Vladimir",
year = "2022",
abstract = "Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields.",
publisher = "Georg Thieme Verlag",
journal = "Synthesis",
title = "Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives",
volume = "54",
number = "12",
pages = "2839-2848",
doi = "10.1055/a-1758-6312"
}

Petković, M., Jovanović, M., Jovanović, P., Simić, M., Tasić, G.,& Savić, V.. (2022). Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives. in Synthesis
Georg Thieme Verlag., 54(12), 2839-2848.
https://doi.org/10.1055/a-1758-6312

Petković M, Jovanović M, Jovanović P, Simić M, Tasić G, Savić V. Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives. in Synthesis. 2022;54(12):2839-2848.
doi:10.1055/a-1758-6312 .

Petković, Miloš, Jovanović, Miloš, Jovanović, Predrag, Simić, Milena, Tasić, Gordana, Savić, Vladimir, "Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives" in Synthesis, 54, no. 12 (2022):2839-2848,
https://doi.org/10.1055/a-1758-6312 . .

TY  - GEN
AU  - Ružić, Dušan
AU  - Ellinger, Bernhard
AU  - Đoković, Nemanja
AU  - Santibanez, Juan
AU  - Ganesan, A.
AU  - Pavić, Aleksandar
AU  - Srdić Rajić, Tatjana
AU  - Petković, Miloš
AU  - Nikolić, Katarina
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4951
PB  - Institute Pasteur, France
T2  - Journal Club on Drug Design, Institute Pasteur, Paris, France November 25 2022
T1  - Identification of novel 1-benzhydryl-piperazine derivatives as Histone Deacetylase inhibitors using Fragment-based drug design strategy
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4951
ER  - 

@misc{
author = "Ružić, Dušan and Ellinger, Bernhard and Đoković, Nemanja and Santibanez, Juan and Ganesan, A. and Pavić, Aleksandar and Srdić Rajić, Tatjana and Petković, Miloš and Nikolić, Katarina",
year = "2022",
publisher = "Institute Pasteur, France",
journal = "Journal Club on Drug Design, Institute Pasteur, Paris, France November 25 2022",
title = "Identification of novel 1-benzhydryl-piperazine derivatives as Histone Deacetylase inhibitors using Fragment-based drug design strategy",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4951"
}

Ružić, D., Ellinger, B., Đoković, N., Santibanez, J., Ganesan, A., Pavić, A., Srdić Rajić, T., Petković, M.,& Nikolić, K.. (2022). Identification of novel 1-benzhydryl-piperazine derivatives as Histone Deacetylase inhibitors using Fragment-based drug design strategy. in Journal Club on Drug Design, Institute Pasteur, Paris, France November 25 2022
Institute Pasteur, France..
https://hdl.handle.net/21.15107/rcub_farfar_4951

Ružić D, Ellinger B, Đoković N, Santibanez J, Ganesan A, Pavić A, Srdić Rajić T, Petković M, Nikolić K. Identification of novel 1-benzhydryl-piperazine derivatives as Histone Deacetylase inhibitors using Fragment-based drug design strategy. in Journal Club on Drug Design, Institute Pasteur, Paris, France November 25 2022. 2022;.
https://hdl.handle.net/21.15107/rcub_farfar_4951 .

Ružić, Dušan, Ellinger, Bernhard, Đoković, Nemanja, Santibanez, Juan, Ganesan, A., Pavić, Aleksandar, Srdić Rajić, Tatjana, Petković, Miloš, Nikolić, Katarina, "Identification of novel 1-benzhydryl-piperazine derivatives as Histone Deacetylase inhibitors using Fragment-based drug design strategy" in Journal Club on Drug Design, Institute Pasteur, Paris, France November 25 2022 (2022),
https://hdl.handle.net/21.15107/rcub_farfar_4951 .

TY  - CONF
AU  - Čarapić, Marija
AU  - Marković, Bojan
AU  - Petković, Miloš
AU  - Nikolić, Katarina
AU  - Agbaba, Danica
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4741
PB  - European Research Network on Signal Transduction CA18133
C3  - 2nd Transatlantic ECI GPCR Symposium - Early Career Investigators – July 6-7, 2022, Online event
T1  - Characterisation of novel impurity of ziprasidone with NMR spectroscopy and UPLC-MS/MS
SP  - 74
EP  - 74
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4741
ER  - 

@conference{
author = "Čarapić, Marija and Marković, Bojan and Petković, Miloš and Nikolić, Katarina and Agbaba, Danica",
year = "2022",
publisher = "European Research Network on Signal Transduction CA18133",
journal = "2nd Transatlantic ECI GPCR Symposium - Early Career Investigators – July 6-7, 2022, Online event",
title = "Characterisation of novel impurity of ziprasidone with NMR spectroscopy and UPLC-MS/MS",
pages = "74-74",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4741"
}

Čarapić, M., Marković, B., Petković, M., Nikolić, K.,& Agbaba, D.. (2022). Characterisation of novel impurity of ziprasidone with NMR spectroscopy and UPLC-MS/MS. in 2nd Transatlantic ECI GPCR Symposium - Early Career Investigators – July 6-7, 2022, Online event
European Research Network on Signal Transduction CA18133., 74-74.
https://hdl.handle.net/21.15107/rcub_farfar_4741

Čarapić M, Marković B, Petković M, Nikolić K, Agbaba D. Characterisation of novel impurity of ziprasidone with NMR spectroscopy and UPLC-MS/MS. in 2nd Transatlantic ECI GPCR Symposium - Early Career Investigators – July 6-7, 2022, Online event. 2022;:74-74.
https://hdl.handle.net/21.15107/rcub_farfar_4741 .

Čarapić, Marija, Marković, Bojan, Petković, Miloš, Nikolić, Katarina, Agbaba, Danica, "Characterisation of novel impurity of ziprasidone with NMR spectroscopy and UPLC-MS/MS" in 2nd Transatlantic ECI GPCR Symposium - Early Career Investigators – July 6-7, 2022, Online event (2022):74-74,
https://hdl.handle.net/21.15107/rcub_farfar_4741 .

TY  - CONF
AU  - Ružić, Dušan
AU  - Đoković, Nemanja
AU  - Petković, Miloš
AU  - Gul, Sheraz
AU  - Lahtela‐Kakkonen, Maija
AU  - Ganesan, A.
AU  - Nikolić, Katarina
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4739
PB  - American Chemical Society Division of Medicinal Chemistry
C3  - 37th ACS National Medicinal Chemistry Symposium - American Chemical Society Division of Medicinal Chemistry, Book of Abstracts
T1  - Computer-aided drug design and evaluation of selective inhibitors against cytoplasmic histone deacetylases
SP  - 125
EP  - 125
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4739
ER  - 

@conference{
author = "Ružić, Dušan and Đoković, Nemanja and Petković, Miloš and Gul, Sheraz and Lahtela‐Kakkonen, Maija and Ganesan, A. and Nikolić, Katarina",
year = "2022",
publisher = "American Chemical Society Division of Medicinal Chemistry",
journal = "37th ACS National Medicinal Chemistry Symposium - American Chemical Society Division of Medicinal Chemistry, Book of Abstracts",
title = "Computer-aided drug design and evaluation of selective inhibitors against cytoplasmic histone deacetylases",
pages = "125-125",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4739"
}

Ružić, D., Đoković, N., Petković, M., Gul, S., Lahtela‐Kakkonen, M., Ganesan, A.,& Nikolić, K.. (2022). Computer-aided drug design and evaluation of selective inhibitors against cytoplasmic histone deacetylases. in 37th ACS National Medicinal Chemistry Symposium - American Chemical Society Division of Medicinal Chemistry, Book of Abstracts
American Chemical Society Division of Medicinal Chemistry., 125-125.
https://hdl.handle.net/21.15107/rcub_farfar_4739

Ružić D, Đoković N, Petković M, Gul S, Lahtela‐Kakkonen M, Ganesan A, Nikolić K. Computer-aided drug design and evaluation of selective inhibitors against cytoplasmic histone deacetylases. in 37th ACS National Medicinal Chemistry Symposium - American Chemical Society Division of Medicinal Chemistry, Book of Abstracts. 2022;:125-125.
https://hdl.handle.net/21.15107/rcub_farfar_4739 .

Ružić, Dušan, Đoković, Nemanja, Petković, Miloš, Gul, Sheraz, Lahtela‐Kakkonen, Maija, Ganesan, A., Nikolić, Katarina, "Computer-aided drug design and evaluation of selective inhibitors against cytoplasmic histone deacetylases" in 37th ACS National Medicinal Chemistry Symposium - American Chemical Society Division of Medicinal Chemistry, Book of Abstracts (2022):125-125,
https://hdl.handle.net/21.15107/rcub_farfar_4739 .

TY  - CONF
AU  - Ružić, Dušan
AU  - Đoković, Nemanja
AU  - Petković, Miloš
AU  - Gul, Sheraz
AU  - Lahtela‐Kakkonen, Maija
AU  - Ganesan, A.
AU  - Srdić-Rajić, Tatjana
AU  - Nikolić, Katarina
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4763
PB  - European Federation for Medicinal Chemistry and Chemical Biology (EFMC)
PB  - Société de Chimie Thérapeutique (SCT)
C3  - EFMC-ISMC, XXVII EFMC International Symposium on Medicinal Chemistry, Book of Abstracts
T1  - Rational design and in vitro evaluation of selective inhibitors of cytoplasmic histone deacetylases SIRT2 and HDAC6
SP  - 141
EP  - 141
UR  - https://hdl.handle.net/21.15107/rcub_farfar_4763
ER  - 

@conference{
author = "Ružić, Dušan and Đoković, Nemanja and Petković, Miloš and Gul, Sheraz and Lahtela‐Kakkonen, Maija and Ganesan, A. and Srdić-Rajić, Tatjana and Nikolić, Katarina",
year = "2022",
publisher = "European Federation for Medicinal Chemistry and Chemical Biology (EFMC), Société de Chimie Thérapeutique (SCT)",
journal = "EFMC-ISMC, XXVII EFMC International Symposium on Medicinal Chemistry, Book of Abstracts",
title = "Rational design and in vitro evaluation of selective inhibitors of cytoplasmic histone deacetylases SIRT2 and HDAC6",
pages = "141-141",
url = "https://hdl.handle.net/21.15107/rcub_farfar_4763"
}

Ružić, D., Đoković, N., Petković, M., Gul, S., Lahtela‐Kakkonen, M., Ganesan, A., Srdić-Rajić, T.,& Nikolić, K.. (2022). Rational design and in vitro evaluation of selective inhibitors of cytoplasmic histone deacetylases SIRT2 and HDAC6. in EFMC-ISMC, XXVII EFMC International Symposium on Medicinal Chemistry, Book of Abstracts
European Federation for Medicinal Chemistry and Chemical Biology (EFMC)., 141-141.
https://hdl.handle.net/21.15107/rcub_farfar_4763

Ružić D, Đoković N, Petković M, Gul S, Lahtela‐Kakkonen M, Ganesan A, Srdić-Rajić T, Nikolić K. Rational design and in vitro evaluation of selective inhibitors of cytoplasmic histone deacetylases SIRT2 and HDAC6. in EFMC-ISMC, XXVII EFMC International Symposium on Medicinal Chemistry, Book of Abstracts. 2022;:141-141.
https://hdl.handle.net/21.15107/rcub_farfar_4763 .

Ružić, Dušan, Đoković, Nemanja, Petković, Miloš, Gul, Sheraz, Lahtela‐Kakkonen, Maija, Ganesan, A., Srdić-Rajić, Tatjana, Nikolić, Katarina, "Rational design and in vitro evaluation of selective inhibitors of cytoplasmic histone deacetylases SIRT2 and HDAC6" in EFMC-ISMC, XXVII EFMC International Symposium on Medicinal Chemistry, Book of Abstracts (2022):141-141,
https://hdl.handle.net/21.15107/rcub_farfar_4763 .

TY  - JOUR
AU  - Božić, Bojan
AU  - Lađarević, Jelena
AU  - Petković, Miloš
AU  - Mijin, Dušan
AU  - Stavber, Stojan
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4433
AB  - The susceptibility of the carbonyl group towards nucleophilic attack affords the construction of various organic compounds. Thus, investigations of carbonyl activation applying greener methodologies are highly important. In the present work, among the investigated N-halo compounds, N-fluorobenzenesulfonimide (NFSi) has been found as an efficient and selective catalyst in the reaction of direct esterification of aryl and alkyl carboxylic acids supported by microwave (MW) irradiation. The comprehensive esterification of different benzoic acids and mono-, di-and tri-carboxy alkyl derivatives was performed, whereby significant reaction time reductions were achieved. The presented method used NFSi as an easily manipulatable, non-metal, water-and air-tolerant catalyst, allowing simple synthetic and isolation procedures and energy saving, compared to conventional methodologies. Importantly, in contrast to esterification under thermal conditions, where N-halo compounds behave as pre-catalysts, in the MW-supported protocol, a distinct reaction mechanism has been proposed that assumes NFSi as a sustainable catalyst. Moreover, a scale-up of the industrially important derivative was performed.
PB  - MDPI
T2  - Catalysts
T1  - Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide
VL  - 12
IS  - 11
DO  - 10.3390/catal12111413
ER  - 

@article{
author = "Božić, Bojan and Lađarević, Jelena and Petković, Miloš and Mijin, Dušan and Stavber, Stojan",
year = "2022",
abstract = "The susceptibility of the carbonyl group towards nucleophilic attack affords the construction of various organic compounds. Thus, investigations of carbonyl activation applying greener methodologies are highly important. In the present work, among the investigated N-halo compounds, N-fluorobenzenesulfonimide (NFSi) has been found as an efficient and selective catalyst in the reaction of direct esterification of aryl and alkyl carboxylic acids supported by microwave (MW) irradiation. The comprehensive esterification of different benzoic acids and mono-, di-and tri-carboxy alkyl derivatives was performed, whereby significant reaction time reductions were achieved. The presented method used NFSi as an easily manipulatable, non-metal, water-and air-tolerant catalyst, allowing simple synthetic and isolation procedures and energy saving, compared to conventional methodologies. Importantly, in contrast to esterification under thermal conditions, where N-halo compounds behave as pre-catalysts, in the MW-supported protocol, a distinct reaction mechanism has been proposed that assumes NFSi as a sustainable catalyst. Moreover, a scale-up of the industrially important derivative was performed.",
publisher = "MDPI",
journal = "Catalysts",
title = "Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide",
volume = "12",
number = "11",
doi = "10.3390/catal12111413"
}

Božić, B., Lađarević, J., Petković, M., Mijin, D.,& Stavber, S.. (2022). Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide. in Catalysts
MDPI., 12(11).
https://doi.org/10.3390/catal12111413

Božić B, Lađarević J, Petković M, Mijin D, Stavber S. Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide. in Catalysts. 2022;12(11).
doi:10.3390/catal12111413 .

Božić, Bojan, Lađarević, Jelena, Petković, Miloš, Mijin, Dušan, Stavber, Stojan, "Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide" in Catalysts, 12, no. 11 (2022),
https://doi.org/10.3390/catal12111413 . .

TY  - CONF
AU  - Samardžić, Stevan
AU  - Maksimović, Zoran
AU  - Đorđić, Marija
AU  - Stanojković, Tatjana
AU  - Petković, Miloš
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5104
AB  - INTRODUCTION:
False indigo-bush (Amorpha fruticosa L., Fabaceae) is an invasive shrub native to central and eastern North America. In Serbia,
it can be found along roads, railways, and riverbeds, where it spreads easily. Previous studies have shown that A. fruticosa
contains several classes of secondary metabolites (e.g. rotenoids, isoflavonoids, prenylflavanones, chalcones, and stilbe-
noids) and exhibits various biological activities (e.g. antioxidant, anti-inflammatory, antidiabetic, insecticidal).
OBJECTIVES:
This study aimed to examine the in vitro cytotoxic activity of prenylated phenolic constituents of false indigo-bush.
METHOD / DESIGN:
An aliquot (0.82 g) of ethanol-soluble part of n-hexane fruit extract (1:10, m/V) was loaded onto silica gel column (3 × 43 cm)
and eluted with mixtures of n-hexane and ethyl acetate (100:0 _ 0:100, V/V). 96 Fractions were collected, analyzed by silica
gel TLC and combined based on chemical composition similarity. Compound 1 (6.9 mg) precipitated as the white powder
during solvent removal from the united fractions 59–69. The pooled fractions 89–92 (80.6 mg) and 95–96 (59.6 mg) gave
compounds 2 (29.8 mg, Rf = 0.5) and 3 (5.8 mg, Rf = 0.53), respectively, after separation by preparative silica gel TLC in a
solvent system consisting of n-hexane, ethyl acetate and formic acid (80:20:1, V/V/V). The structure determination of the iso-
lated prenylated phenols were based on their UV, MS, and 1
H and 13
C NMR spectra. MTT assay was employed to assess their
cytotoxicity against human tumor cell lines (HeLa, HT-29
, HCT-116
, LS174) derived from the cervix adenocarcinoma and colorec-
tal carcinomas, as well as human fetal lung fibroblasts (MRC-5). cis-Diamminedichloroplatinum (CDDP) was used as a control
substance. The activity is expressed as the IC 50 value, i.e. the concentration of the tested substance that led to 50% inhibition
of survival, compared to the vehicle-treated control group. The statistical analysis was performed using the Student’s t-test.
RESULTS:
Based on a comparison of recorded spectral data and literature data, compound 1 was identified as 5,7-dihydroxy-8-gera-
nylflavanone, compound 2 as 2-carboxy-3,5-dihydroxy-4-geranylbibenzyl, and compound 3 as 2-carboxy-3-hydroxy-4-pre-
nyl-5-metoxybibenzyl (amorfrutin A). All tested constituents showed cytotoxicity with the IC50 values in the range 10.55–
166.11 μg/mL. The non-selectivity of compounds 2 and 3 could be observed. On the other hand, compound 1 was selective
and exhibited pronounced activity against the HeLa cell line (IC 50 = 10.55 μg/mL). HT-29 (IC 50 = 122.28 μg/mL) and HCT-116
(IC 50 = 147.09 μg/mL) cancer cell lines, as well as normal cell line MRC-5 (IC50 = 166.11 μg/mL), were less susceptible to the action of compound 1, whereas the survival of LS174 cell line was not affected at all by compound 1 in the tested concen-
tration range. The effectiveness of the control substance CDDP in reducing the survival of the HeLa cancer cell line was the
highest (IC50 = 5.20 μg/mL). It should be emphasized that CDDP, among tested substances, was also the most toxic against
the MRC-5 cell line (IC 50 = 8.28 μg/mL). IC 50 values ranges of compounds 2 and 3 were 31.97–56.29 μg/mL and 35.67–53.21
μg/mL, respectively.
CONCLUSIONS:
5,7-Dihydroxy-8-geranylflavanone, the constituent of false indigo-bush fruit, exhibited strong and selective activity against
the human cervix adenocarcinoma cell line in the MTT assay, therefore, its cytotoxic potential can be considered significant.
Further studies are needed to fully assess the demonstrated effect.
PB  - University Prince of Songkla, Thailand
PB  - University of Novi Sad, Faculty of Sciences, Serbia, Novi Sad
C3  - The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts
T1  - Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.)
SP  - 126
EP  - 127
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5104
ER  - 

@conference{
author = "Samardžić, Stevan and Maksimović, Zoran and Đorđić, Marija and Stanojković, Tatjana and Petković, Miloš",
year = "2021",
abstract = "INTRODUCTION:
False indigo-bush (Amorpha fruticosa L., Fabaceae) is an invasive shrub native to central and eastern North America. In Serbia,
it can be found along roads, railways, and riverbeds, where it spreads easily. Previous studies have shown that A. fruticosa
contains several classes of secondary metabolites (e.g. rotenoids, isoflavonoids, prenylflavanones, chalcones, and stilbe-
noids) and exhibits various biological activities (e.g. antioxidant, anti-inflammatory, antidiabetic, insecticidal).
OBJECTIVES:
This study aimed to examine the in vitro cytotoxic activity of prenylated phenolic constituents of false indigo-bush.
METHOD / DESIGN:
An aliquot (0.82 g) of ethanol-soluble part of n-hexane fruit extract (1:10, m/V) was loaded onto silica gel column (3 × 43 cm)
and eluted with mixtures of n-hexane and ethyl acetate (100:0 _ 0:100, V/V). 96 Fractions were collected, analyzed by silica
gel TLC and combined based on chemical composition similarity. Compound 1 (6.9 mg) precipitated as the white powder
during solvent removal from the united fractions 59–69. The pooled fractions 89–92 (80.6 mg) and 95–96 (59.6 mg) gave
compounds 2 (29.8 mg, Rf = 0.5) and 3 (5.8 mg, Rf = 0.53), respectively, after separation by preparative silica gel TLC in a
solvent system consisting of n-hexane, ethyl acetate and formic acid (80:20:1, V/V/V). The structure determination of the iso-
lated prenylated phenols were based on their UV, MS, and 1
H and 13
C NMR spectra. MTT assay was employed to assess their
cytotoxicity against human tumor cell lines (HeLa, HT-29
, HCT-116
, LS174) derived from the cervix adenocarcinoma and colorec-
tal carcinomas, as well as human fetal lung fibroblasts (MRC-5). cis-Diamminedichloroplatinum (CDDP) was used as a control
substance. The activity is expressed as the IC 50 value, i.e. the concentration of the tested substance that led to 50% inhibition
of survival, compared to the vehicle-treated control group. The statistical analysis was performed using the Student’s t-test.
RESULTS:
Based on a comparison of recorded spectral data and literature data, compound 1 was identified as 5,7-dihydroxy-8-gera-
nylflavanone, compound 2 as 2-carboxy-3,5-dihydroxy-4-geranylbibenzyl, and compound 3 as 2-carboxy-3-hydroxy-4-pre-
nyl-5-metoxybibenzyl (amorfrutin A). All tested constituents showed cytotoxicity with the IC50 values in the range 10.55–
166.11 μg/mL. The non-selectivity of compounds 2 and 3 could be observed. On the other hand, compound 1 was selective
and exhibited pronounced activity against the HeLa cell line (IC 50 = 10.55 μg/mL). HT-29 (IC 50 = 122.28 μg/mL) and HCT-116
(IC 50 = 147.09 μg/mL) cancer cell lines, as well as normal cell line MRC-5 (IC50 = 166.11 μg/mL), were less susceptible to the action of compound 1, whereas the survival of LS174 cell line was not affected at all by compound 1 in the tested concen-
tration range. The effectiveness of the control substance CDDP in reducing the survival of the HeLa cancer cell line was the
highest (IC50 = 5.20 μg/mL). It should be emphasized that CDDP, among tested substances, was also the most toxic against
the MRC-5 cell line (IC 50 = 8.28 μg/mL). IC 50 values ranges of compounds 2 and 3 were 31.97–56.29 μg/mL and 35.67–53.21
μg/mL, respectively.
CONCLUSIONS:
5,7-Dihydroxy-8-geranylflavanone, the constituent of false indigo-bush fruit, exhibited strong and selective activity against
the human cervix adenocarcinoma cell line in the MTT assay, therefore, its cytotoxic potential can be considered significant.
Further studies are needed to fully assess the demonstrated effect.",
publisher = "University Prince of Songkla, Thailand, University of Novi Sad, Faculty of Sciences, Serbia, Novi Sad",
journal = "The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts",
title = "Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.)",
pages = "126-127",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5104"
}

Samardžić, S., Maksimović, Z., Đorđić, M., Stanojković, T.,& Petković, M.. (2021). Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.). in The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts
University Prince of Songkla, Thailand., 126-127.
https://hdl.handle.net/21.15107/rcub_farfar_5104

Samardžić S, Maksimović Z, Đorđić M, Stanojković T, Petković M. Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.). in The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts. 2021;:126-127.
https://hdl.handle.net/21.15107/rcub_farfar_5104 .

Samardžić, Stevan, Maksimović, Zoran, Đorđić, Marija, Stanojković, Tatjana, Petković, Miloš, "Cytotoxic prenylated phenols of false indigo-bush (Amorpha fruticosa L.)" in The International Bioscience Conference and the 8th International PSU – UNS Bioscience Conference - IBSC2021 Book of Abstracts (2021):126-127,
https://hdl.handle.net/21.15107/rcub_farfar_5104 .

TY  - CONF
AU  - Simić, Milena
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Žižak, Željko
AU  - Tasić, Gordana
AU  - Jovanović, Miloš
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5391
AB  - Kumarini su heterociklična jedinjenja veoma rasprostranjen u prirodi. Kao privilegovana struktura,
ovaj molekul se nalazi i u velikom broju sintetskih derivata sa značajnom biološkom aktivnošću.
Posebno su interesantni hibridi koji sadrže dve farmakofore, od kojih je jedna kumarin. Cilj ovog
istraživanja bio je sinteza serije jednostavnih novih 4-azolil kumarina i evaluacija njihove in vitro
citotoksičnosti prema humanim kancerskim ćelijskim linijama HeLa, K562, MCF-7 i MDA-MB-
453.
AB  - Coumarins are heterocyclic compounds widely distributed in nature. As a privileged structure,
coumarin is also found in a large number of synthetic molecules with important biological activity.
Particularly interesting compounds are coumarin-containing hybrids, compounds with two or more
pharmacophores. The aim of this work was preparation of simple novel azolyl-coumarin hybrids
and evaluation of their cytotoxic effect on human cancer cells, HeLa, K562, MDA-MB-453 and
MCF-7.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija
T1  - Sinteza i antikancerski potencijal 4-azolilkumarina
T1  - Synthesis and anticancer potential of 4-azolylcoumarins
SP  - 88
EP  - 88
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5391
ER  - 

@conference{
author = "Simić, Milena and Jovanović, Predrag and Petković, Miloš and Žižak, Željko and Tasić, Gordana and Jovanović, Miloš and Savić, Vladimir",
year = "2021",
abstract = "Kumarini su heterociklična jedinjenja veoma rasprostranjen u prirodi. Kao privilegovana struktura,
ovaj molekul se nalazi i u velikom broju sintetskih derivata sa značajnom biološkom aktivnošću.
Posebno su interesantni hibridi koji sadrže dve farmakofore, od kojih je jedna kumarin. Cilj ovog
istraživanja bio je sinteza serije jednostavnih novih 4-azolil kumarina i evaluacija njihove in vitro
citotoksičnosti prema humanim kancerskim ćelijskim linijama HeLa, K562, MCF-7 i MDA-MB-
453., Coumarins are heterocyclic compounds widely distributed in nature. As a privileged structure,
coumarin is also found in a large number of synthetic molecules with important biological activity.
Particularly interesting compounds are coumarin-containing hybrids, compounds with two or more
pharmacophores. The aim of this work was preparation of simple novel azolyl-coumarin hybrids
and evaluation of their cytotoxic effect on human cancer cells, HeLa, K562, MDA-MB-453 and
MCF-7.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija",
title = "Sinteza i antikancerski potencijal 4-azolilkumarina, Synthesis and anticancer potential of 4-azolylcoumarins",
pages = "88-88",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5391"
}

Simić, M., Jovanović, P., Petković, M., Žižak, Ž., Tasić, G., Jovanović, M.,& Savić, V.. (2021). Sinteza i antikancerski potencijal 4-azolilkumarina. in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija
Srpsko hemijsko društvo, Beograd., 88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5391

Simić M, Jovanović P, Petković M, Žižak Ž, Tasić G, Jovanović M, Savić V. Sinteza i antikancerski potencijal 4-azolilkumarina. in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija. 2021;:88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5391 .

Simić, Milena, Jovanović, Predrag, Petković, Miloš, Žižak, Željko, Tasić, Gordana, Jovanović, Miloš, Savić, Vladimir, "Sinteza i antikancerski potencijal 4-azolilkumarina" in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija (2021):88-88,
https://hdl.handle.net/21.15107/rcub_farfar_5391 .