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  - 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  - 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  - 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  - 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 .

TY  - JOUR
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Besu, Irina
AU  - Žižak, Željko
AU  - Aleksić, Ivana
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3935
AB  - Several coumarin derivatives with a directly attached azole substituent at C‐4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K‐562, MDA‐MB‐53, and MCF‐7) demonstrated different sensitivities. The best response in the MTT (3‐(4,5‐dimethyl‐2‐thiazolyl)‐ 2,5‐diphenyl‐2H‐tetrazolium bromide) assay was shown by K‐562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole‐substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF‐7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4‐azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment‐like structures with MW <300 and clog P <3 offers enough flexibility to fine‐tune their drug‐like properties.
PB  - John Wiley and Sons Inc
T2  - Archiv der Pharmazie
T1  - Fragment-type 4-azolylcoumarin derivatives with anticancer properties
DO  - 10.1002/ardp.202100238
ER  - 

@article{
author = "Simić, Milena and Petković, Miloš and Jovanović, Predrag and Jovanović, Miloš and Tasić, Gordana and Besu, Irina and Žižak, Željko and Aleksić, Ivana and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2021",
abstract = "Several coumarin derivatives with a directly attached azole substituent at C‐4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K‐562, MDA‐MB‐53, and MCF‐7) demonstrated different sensitivities. The best response in the MTT (3‐(4,5‐dimethyl‐2‐thiazolyl)‐ 2,5‐diphenyl‐2H‐tetrazolium bromide) assay was shown by K‐562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole‐substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF‐7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4‐azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment‐like structures with MW <300 and clog P <3 offers enough flexibility to fine‐tune their drug‐like properties.",
publisher = "John Wiley and Sons Inc",
journal = "Archiv der Pharmazie",
title = "Fragment-type 4-azolylcoumarin derivatives with anticancer properties",
doi = "10.1002/ardp.202100238"
}

Simić, M., Petković, M., Jovanović, P., Jovanović, M., Tasić, G., Besu, I., Žižak, Ž., Aleksić, I., Nikodinović-Runić, J.,& Savić, V.. (2021). Fragment-type 4-azolylcoumarin derivatives with anticancer properties. in Archiv der Pharmazie
John Wiley and Sons Inc..
https://doi.org/10.1002/ardp.202100238

Simić M, Petković M, Jovanović P, Jovanović M, Tasić G, Besu I, Žižak Ž, Aleksić I, Nikodinović-Runić J, Savić V. Fragment-type 4-azolylcoumarin derivatives with anticancer properties. in Archiv der Pharmazie. 2021;.
doi:10.1002/ardp.202100238 .

Simić, Milena, Petković, Miloš, Jovanović, Predrag, Jovanović, Miloš, Tasić, Gordana, Besu, Irina, Žižak, Željko, Aleksić, Ivana, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Fragment-type 4-azolylcoumarin derivatives with anticancer properties" in Archiv der Pharmazie (2021),
https://doi.org/10.1002/ardp.202100238 . .

TY  - JOUR
AU  - Simić, Milena
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Tasić, Gordana
AU  - Jovanović, Miloš
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3908
AB  - Octahydro-dipyrroloquinoline skeleton is the building component of a very few naturally occurring compounds. Nevertheless, these natural products have been attractive synthetic targets, and their study commanded development of efficient synthesis of this core. While the reported methods are based on the dimerization procedure of N-arylpyrrolidines of N-arylhomopropargyl amines, our approach relay on dipolar cycloaddition/amination sequence. This strategic approach allows sequential introduction of aromatic moieties increasing the product diversity and hence may be useful in further exploration of incargranine B or seneciobipyrrolidine derivatives.
PB  - Wiley, HeteroCorporation
T2  - Journal of Heterocyclic Chemistry
T1  - Toward the synthesis of incargranine B and seneciobipyrrolidine. Synthesis of octahydro-dipyrroloquinoline skeleton via dipolar cycloaddition/amination sequence
DO  - 10.1002/jhet.4303
ER  - 

@article{
author = "Simić, Milena and Jovanović, Predrag and Petković, Miloš and Tasić, Gordana and Jovanović, Miloš and Savić, Vladimir",
year = "2021",
abstract = "Octahydro-dipyrroloquinoline skeleton is the building component of a very few naturally occurring compounds. Nevertheless, these natural products have been attractive synthetic targets, and their study commanded development of efficient synthesis of this core. While the reported methods are based on the dimerization procedure of N-arylpyrrolidines of N-arylhomopropargyl amines, our approach relay on dipolar cycloaddition/amination sequence. This strategic approach allows sequential introduction of aromatic moieties increasing the product diversity and hence may be useful in further exploration of incargranine B or seneciobipyrrolidine derivatives.",
publisher = "Wiley, HeteroCorporation",
journal = "Journal of Heterocyclic Chemistry",
title = "Toward the synthesis of incargranine B and seneciobipyrrolidine. Synthesis of octahydro-dipyrroloquinoline skeleton via dipolar cycloaddition/amination sequence",
doi = "10.1002/jhet.4303"
}

Simić, M., Jovanović, P., Petković, M., Tasić, G., Jovanović, M.,& Savić, V.. (2021). Toward the synthesis of incargranine B and seneciobipyrrolidine. Synthesis of octahydro-dipyrroloquinoline skeleton via dipolar cycloaddition/amination sequence. in Journal of Heterocyclic Chemistry
Wiley, HeteroCorporation..
https://doi.org/10.1002/jhet.4303

Simić M, Jovanović P, Petković M, Tasić G, Jovanović M, Savić V. Toward the synthesis of incargranine B and seneciobipyrrolidine. Synthesis of octahydro-dipyrroloquinoline skeleton via dipolar cycloaddition/amination sequence. in Journal of Heterocyclic Chemistry. 2021;.
doi:10.1002/jhet.4303 .

Simić, Milena, Jovanović, Predrag, Petković, Miloš, Tasić, Gordana, Jovanović, Miloš, Savić, Vladimir, "Toward the synthesis of incargranine B and seneciobipyrrolidine. Synthesis of octahydro-dipyrroloquinoline skeleton via dipolar cycloaddition/amination sequence" in Journal of Heterocyclic Chemistry (2021),
https://doi.org/10.1002/jhet.4303 . .

TY  - JOUR
AU  - Lukić, Vera
AU  - Micić, Ružica
AU  - Arsić, Biljana
AU  - Mitić, Milan
AU  - Jovanović, Miloš
AU  - Pavlović, Aleksandra
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4050
AB  - The samples of plant material suspected to contain new psychoactive substances are very often the subject of chemical-toxicological analyses. Gas chromatography-mass spectrometry (MS), liquid chromatography-quadrupole time-of-flight-MS, and liquid chromatography-tandem MS were applied with the aim to identify synthetic cannabinoid, methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate (MMB-CHMICA) without the analytical standard, which is very often the case when a new drug arrives. The structure of compound was also confirmed by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and conformational analysis. After identification, methanolic extract of plant material containing MMB-CHMICA was successfully used for developing a multiple reaction monitoring method on liquid chromatography-tandem MS instrument. The optimization procedure is shown in detail. The complete fragmentation pattern and also the optimization of the extraction procedure of MMB-CHMICA from plant material were shown. The obtained data are useful for forensic, toxicological, and clinical purposes.
PB  - De Gruyter Open Ltd
T2  - Open Chemistry
T1  - Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques
VL  - 19
IS  - 1
SP  - 1259
EP  - 1273
DO  - 10.1515/chem-2021-0113
ER  - 

@article{
author = "Lukić, Vera and Micić, Ružica and Arsić, Biljana and Mitić, Milan and Jovanović, Miloš and Pavlović, Aleksandra",
year = "2021",
abstract = "The samples of plant material suspected to contain new psychoactive substances are very often the subject of chemical-toxicological analyses. Gas chromatography-mass spectrometry (MS), liquid chromatography-quadrupole time-of-flight-MS, and liquid chromatography-tandem MS were applied with the aim to identify synthetic cannabinoid, methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate (MMB-CHMICA) without the analytical standard, which is very often the case when a new drug arrives. The structure of compound was also confirmed by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy and conformational analysis. After identification, methanolic extract of plant material containing MMB-CHMICA was successfully used for developing a multiple reaction monitoring method on liquid chromatography-tandem MS instrument. The optimization procedure is shown in detail. The complete fragmentation pattern and also the optimization of the extraction procedure of MMB-CHMICA from plant material were shown. The obtained data are useful for forensic, toxicological, and clinical purposes.",
publisher = "De Gruyter Open Ltd",
journal = "Open Chemistry",
title = "Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques",
volume = "19",
number = "1",
pages = "1259-1273",
doi = "10.1515/chem-2021-0113"
}

Lukić, V., Micić, R., Arsić, B., Mitić, M., Jovanović, M.,& Pavlović, A.. (2021). Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques. in Open Chemistry
De Gruyter Open Ltd., 19(1), 1259-1273.
https://doi.org/10.1515/chem-2021-0113

Lukić V, Micić R, Arsić B, Mitić M, Jovanović M, Pavlović A. Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques. in Open Chemistry. 2021;19(1):1259-1273.
doi:10.1515/chem-2021-0113 .

Lukić, Vera, Micić, Ružica, Arsić, Biljana, Mitić, Milan, Jovanović, Miloš, Pavlović, Aleksandra, "Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques" in Open Chemistry, 19, no. 1 (2021):1259-1273,
https://doi.org/10.1515/chem-2021-0113 . .

TY  - THES
AU  - Jovanović, Miloš
PY  - 2020
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7643
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:22722/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=18382089
UR  - https://nardus.mpn.gov.rs/handle/123456789/17505
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3720
AB  - Ramnolipidi su ekološki prihvatljivi biosurfaktanti koje proizvodi bakterija Pseudomonas aeruginosa. Zbog interesantnog biološkog profila i odličnih fizičko-hemijskih svojstava nalaze primenu u biotehnologiji, bioremedijaciji i medicini. Njihova šira i ekonomski prihvatljivija primena je međutim značajno otežana činjenicom da se teško mogu dobiti u većim količinama i u čistoj formi. Kao posledica toga istraživanja u smeru strukturnih modifikacija i sinteze analoga ramnolipida nisu još uvek zaživela, samim tim, fizičko-hemijska i biološka svojstva srodnih molekula nisu još uvek dovoljno istražena. Imajuči u vidu neekonomičnost sinteze ramnolipida cilj ovog istraživanja bio je pronaći sintetski pristupačne molekule koji bi imali isti ili bolji biološki ili fizičko-hemijski profil od samih prirodnih ramnolipida. Korišćenjem (R)-3-hidroksikiseline kao osnovnog strukturnog fragmenta sintetisani su šećerni, heterociklični i peptidni analozi ramnolipida i ispitivane njihove fizičko-hemijske i antimikrobne osobine. Zamenom ramnoze drugim šećerima smanjuje se cena proizvodnje ovih molekula dok se istovremeno očuvava površinska aktivnost i biorazgradivost. Zamenom ramnoze peptidima dobijajena je serija jedinjenja sa anti-adhezivnim dejstvom na Candida albicans (BFIC50 = 4,5 μg/mL). Najaktivniji derivati su konjugati leucina i 3-hidroksikiselina koje sadrže benzil estar. SAR studijom je pokazano da je optimalan broj aminokiselina u bočnom nizu 1-2, kao i da se anti-biofilm aktivnost povećava sa produženjem alifatičnog niza 3-hidroksikiselina. Ova jedinjenja inhibiraju formiranje biofilma sprečavanjem adhezije C. albicans na abiotsku i biološku površinu.Pored ramnolipida, i mali molekuli koji pripadaju bromopirolskim alkaloidima takođe ispoljavaju antimikrobna i anti-biofilm svojstva. Longamid B je jedan od naistraživanijih molekula ove grupe. Poznata je njegova antimikrobna aktivnost na bakterijske sojeve Bacillus subtilis i Staphylococcus aureus. Iz tog razloga predstavlja atraktivan target za totalnu sintezu i šire proučavanje hemijskog prostora definisanog njegovom strukturom. Pretpostavljeno je da se osnovni skelet bromopirolskih alkaloida, može dobiti intramolekulskom nukleofilnom adicijom na alene. Ispitivanjem ciklizacionih reakcija aminoalena u prisustvu serije metalnih soli došlo se do optimalnih uslova koji su podrazumevali korišćenje stehiometrijske količine AgNO3. Zahvaljujući hiralnom ciklizacionom prekursoru reakcija ciklizacije se odvijala stereoselektivno. Razvijena metodologija iskorišćena je u sintezi longamida B i stilizina D.U cilju diverzifikacije strukture bromopirolskih alkaloida ispitivane su reakcije i karboaminacije aminoalena katalizovane paladijumom. Ova strategija omogućila je sintezu α-supstituisanih derivata longamida.
AB  - Rhamnolipids are environmentally friendly biosurfactants produced mostly by strains of Pseudomonas aeruginosa. Due to their interesting biological profile and excellent physico-chemical properties, they find application in biotechnology, bioremediation and medicine. The inefficient large scale production, however, still hinders their wider application. Consequently, the research on structural modifications and the synthesis of rhamnolipid analogues is still in the early stages and the physico-chemical and biological properties of related molecules are not yet fully explored. Thus this research aimed to find synthetically accessible molecules which would mimic or enhance the properties of the parent molecule. Using (R)-hydroxy acids as a core building block, the sugar, heterocyclic and peptide analogues of rhamnolipids were synthesised and their physico-chemical and antimicrobial properties evaluated. Replacing rhamnose with other sugars allows for a reduction in production cost whilst preserving the surface active properties and biodegradability of the parent molecules. The replacement of rhamnose with peptides produced a series of molecules with anti-adhesion effect on Candida albicans (BFIC50 = 4,5 μg/mL). The most potent derivatives were conjugates of leucine and benzyl esters of 3-hydroxyacids. The SAR study showed that the optimal number of amino acids in the sidechain was one or two, furthermore, the elongation of the aliphatic chain also improved the anti-biofilm properties of the peptide derivatives. The compounds were found to exert anti-biofilm properties through inhibition of C. albicans adhesion to abiotic and biotic surfaces.Apart from rhamnolipids, small molecules, members of bromopyrrole alkaloid family, also exert antimicrobial and anti-biofilm properties. Longamid B is one of the most studied molecules of this group. Its antimicrobial activity against Bacillus subtilis and Staphylococcus aureus is well known. Therefore it represents an attractive target for total synthesis and the exploration of chemical space around the molecule. Our envisaged strategy was based on the hypothesis that the core structure of bromopyrrole alkaloids could be accessed via intramolecular nucleophilic addition to allene moiety. The investigation of cyclization reactions of aminoallenes in the presence of a series of metal salts uncovered a stoichiometric amount of AgNO3 as the best option for the reaction. The chiral precursor allowed a stereoselective cyclization process. The developed methodology was successfully applied in the synthesis of longamide B and stylisine D.With the aim of diversificating the structure of bromopyrrole alkaloids the carboamination reactions of aminoallenes catalyzed by palladium were also explored. This strategy allowed the synthesis of α-substituted derivatives of longamide B.
PB  - Универзитет у Београду, Фармацеутски факултет
T2  - Универзитет у Београду
T1  - Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija
UR  - https://hdl.handle.net/21.15107/rcub_nardus_17505
ER  - 

@phdthesis{
author = "Jovanović, Miloš",
year = "2020",
abstract = "Ramnolipidi su ekološki prihvatljivi biosurfaktanti koje proizvodi bakterija Pseudomonas aeruginosa. Zbog interesantnog biološkog profila i odličnih fizičko-hemijskih svojstava nalaze primenu u biotehnologiji, bioremedijaciji i medicini. Njihova šira i ekonomski prihvatljivija primena je međutim značajno otežana činjenicom da se teško mogu dobiti u većim količinama i u čistoj formi. Kao posledica toga istraživanja u smeru strukturnih modifikacija i sinteze analoga ramnolipida nisu još uvek zaživela, samim tim, fizičko-hemijska i biološka svojstva srodnih molekula nisu još uvek dovoljno istražena. Imajuči u vidu neekonomičnost sinteze ramnolipida cilj ovog istraživanja bio je pronaći sintetski pristupačne molekule koji bi imali isti ili bolji biološki ili fizičko-hemijski profil od samih prirodnih ramnolipida. Korišćenjem (R)-3-hidroksikiseline kao osnovnog strukturnog fragmenta sintetisani su šećerni, heterociklični i peptidni analozi ramnolipida i ispitivane njihove fizičko-hemijske i antimikrobne osobine. Zamenom ramnoze drugim šećerima smanjuje se cena proizvodnje ovih molekula dok se istovremeno očuvava površinska aktivnost i biorazgradivost. Zamenom ramnoze peptidima dobijajena je serija jedinjenja sa anti-adhezivnim dejstvom na Candida albicans (BFIC50 = 4,5 μg/mL). Najaktivniji derivati su konjugati leucina i 3-hidroksikiselina koje sadrže benzil estar. SAR studijom je pokazano da je optimalan broj aminokiselina u bočnom nizu 1-2, kao i da se anti-biofilm aktivnost povećava sa produženjem alifatičnog niza 3-hidroksikiselina. Ova jedinjenja inhibiraju formiranje biofilma sprečavanjem adhezije C. albicans na abiotsku i biološku površinu.Pored ramnolipida, i mali molekuli koji pripadaju bromopirolskim alkaloidima takođe ispoljavaju antimikrobna i anti-biofilm svojstva. Longamid B je jedan od naistraživanijih molekula ove grupe. Poznata je njegova antimikrobna aktivnost na bakterijske sojeve Bacillus subtilis i Staphylococcus aureus. Iz tog razloga predstavlja atraktivan target za totalnu sintezu i šire proučavanje hemijskog prostora definisanog njegovom strukturom. Pretpostavljeno je da se osnovni skelet bromopirolskih alkaloida, može dobiti intramolekulskom nukleofilnom adicijom na alene. Ispitivanjem ciklizacionih reakcija aminoalena u prisustvu serije metalnih soli došlo se do optimalnih uslova koji su podrazumevali korišćenje stehiometrijske količine AgNO3. Zahvaljujući hiralnom ciklizacionom prekursoru reakcija ciklizacije se odvijala stereoselektivno. Razvijena metodologija iskorišćena je u sintezi longamida B i stilizina D.U cilju diverzifikacije strukture bromopirolskih alkaloida ispitivane su reakcije i karboaminacije aminoalena katalizovane paladijumom. Ova strategija omogućila je sintezu α-supstituisanih derivata longamida., Rhamnolipids are environmentally friendly biosurfactants produced mostly by strains of Pseudomonas aeruginosa. Due to their interesting biological profile and excellent physico-chemical properties, they find application in biotechnology, bioremediation and medicine. The inefficient large scale production, however, still hinders their wider application. Consequently, the research on structural modifications and the synthesis of rhamnolipid analogues is still in the early stages and the physico-chemical and biological properties of related molecules are not yet fully explored. Thus this research aimed to find synthetically accessible molecules which would mimic or enhance the properties of the parent molecule. Using (R)-hydroxy acids as a core building block, the sugar, heterocyclic and peptide analogues of rhamnolipids were synthesised and their physico-chemical and antimicrobial properties evaluated. Replacing rhamnose with other sugars allows for a reduction in production cost whilst preserving the surface active properties and biodegradability of the parent molecules. The replacement of rhamnose with peptides produced a series of molecules with anti-adhesion effect on Candida albicans (BFIC50 = 4,5 μg/mL). The most potent derivatives were conjugates of leucine and benzyl esters of 3-hydroxyacids. The SAR study showed that the optimal number of amino acids in the sidechain was one or two, furthermore, the elongation of the aliphatic chain also improved the anti-biofilm properties of the peptide derivatives. The compounds were found to exert anti-biofilm properties through inhibition of C. albicans adhesion to abiotic and biotic surfaces.Apart from rhamnolipids, small molecules, members of bromopyrrole alkaloid family, also exert antimicrobial and anti-biofilm properties. Longamid B is one of the most studied molecules of this group. Its antimicrobial activity against Bacillus subtilis and Staphylococcus aureus is well known. Therefore it represents an attractive target for total synthesis and the exploration of chemical space around the molecule. Our envisaged strategy was based on the hypothesis that the core structure of bromopyrrole alkaloids could be accessed via intramolecular nucleophilic addition to allene moiety. The investigation of cyclization reactions of aminoallenes in the presence of a series of metal salts uncovered a stoichiometric amount of AgNO3 as the best option for the reaction. The chiral precursor allowed a stereoselective cyclization process. The developed methodology was successfully applied in the synthesis of longamide B and stylisine D.With the aim of diversificating the structure of bromopyrrole alkaloids the carboamination reactions of aminoallenes catalyzed by palladium were also explored. This strategy allowed the synthesis of α-substituted derivatives of longamide B.",
publisher = "Универзитет у Београду, Фармацеутски факултет",
journal = "Универзитет у Београду",
title = "Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija",
url = "https://hdl.handle.net/21.15107/rcub_nardus_17505"
}

Jovanović, M.. (2020). Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija. in Универзитет у Београду
Универзитет у Београду, Фармацеутски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_17505

Jovanović M. Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija. in Универзитет у Београду. 2020;.
https://hdl.handle.net/21.15107/rcub_nardus_17505 .

Jovanović, Miloš, "Sinteza longamida B i analoga ramnolipida i njihova fizičko-hemijska i biološka karakterizacija" in Универзитет у Београду (2020),
https://hdl.handle.net/21.15107/rcub_nardus_17505 .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Simić, Milena
AU  - Tasić, Gordana
AU  - Erić, Slavica
AU  - Savić, Vladimir
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3481
AB  - Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.
PB  - Wiley-Blackwell
T2  - European Journal of Organic Chemistry
T1  - Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
VL  - 2020
IS  - 3
SP  - 295
EP  - 305
DO  - 10.1002/ejoc.201901554
ER  - 

@article{
author = "Jovanović, Miloš and Petković, Miloš and Jovanović, Predrag and Simić, Milena and Tasić, Gordana and Erić, Slavica and Savić, Vladimir",
year = "2020",
abstract = "Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag-catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.",
publisher = "Wiley-Blackwell",
journal = "European Journal of Organic Chemistry",
title = "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives",
volume = "2020",
number = "3",
pages = "295-305",
doi = "10.1002/ejoc.201901554"
}

Jovanović, M., Petković, M., Jovanović, P., Simić, M., Tasić, G., Erić, S.,& Savić, V.. (2020). Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. in European Journal of Organic Chemistry
Wiley-Blackwell., 2020(3), 295-305.
https://doi.org/10.1002/ejoc.201901554

Jovanović M, Petković M, Jovanović P, Simić M, Tasić G, Erić S, Savić V. Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives. in European Journal of Organic Chemistry. 2020;2020(3):295-305.
doi:10.1002/ejoc.201901554 .

Jovanović, Miloš, Petković, Miloš, Jovanović, Predrag, Simić, Milena, Tasić, Gordana, Erić, Slavica, Savić, Vladimir, "Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives" in European Journal of Organic Chemistry, 2020, no. 3 (2020):295-305,
https://doi.org/10.1002/ejoc.201901554 . .

TY  - JOUR
AU  - Gawlik, Maciej
AU  - Savić, Vladimir
AU  - Jovanović, Miloš
AU  - Skibiński, Robert
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3569
AB  - Establishing the metabolism pathway of the drug undergoing the hepatic biotransformation pathway is one of the most important aspects in the preclinical discovery process since the presence of toxic or reactive metabolites may result in drug withdrawal from the market. In this study, we present the structural elucidation of six, not described yet, metabolites of an antipsychotic molecule: molindone. The elucidation of metabolites was supported with a novel photocatalytical approach with the use of WO3 and WS2 assisted photochemical reactions. An UHPLC-ESI-Q-TOF combined system was used for the registration of all obtained metabolite profiles as well as to record the high resolution fragmentation spectra of the observed transformation products. As a reference in the in vitro metabolism simulation method, the incubation with human liver microsomes was used. Chemometric comparison of the obtained profiles pointed out the use of the WO3 approach as being more convenient in the field of drug metabolism studies. Moreover, the photocatalysis was used in the direction of the main drug metabolite synthesis in order to further isolation and characterization.
PB  - MDPI AG
T2  - Molecules
T1  - Mimicking of phase I metabolism reactions of molindone by HLM and photocatalytic methods with the use of UHPLC-MS/MS
VL  - 25
IS  - 6
DO  - 10.3390/molecules25061367
ER  - 

@article{
author = "Gawlik, Maciej and Savić, Vladimir and Jovanović, Miloš and Skibiński, Robert",
year = "2020",
abstract = "Establishing the metabolism pathway of the drug undergoing the hepatic biotransformation pathway is one of the most important aspects in the preclinical discovery process since the presence of toxic or reactive metabolites may result in drug withdrawal from the market. In this study, we present the structural elucidation of six, not described yet, metabolites of an antipsychotic molecule: molindone. The elucidation of metabolites was supported with a novel photocatalytical approach with the use of WO3 and WS2 assisted photochemical reactions. An UHPLC-ESI-Q-TOF combined system was used for the registration of all obtained metabolite profiles as well as to record the high resolution fragmentation spectra of the observed transformation products. As a reference in the in vitro metabolism simulation method, the incubation with human liver microsomes was used. Chemometric comparison of the obtained profiles pointed out the use of the WO3 approach as being more convenient in the field of drug metabolism studies. Moreover, the photocatalysis was used in the direction of the main drug metabolite synthesis in order to further isolation and characterization.",
publisher = "MDPI AG",
journal = "Molecules",
title = "Mimicking of phase I metabolism reactions of molindone by HLM and photocatalytic methods with the use of UHPLC-MS/MS",
volume = "25",
number = "6",
doi = "10.3390/molecules25061367"
}

Gawlik, M., Savić, V., Jovanović, M.,& Skibiński, R.. (2020). Mimicking of phase I metabolism reactions of molindone by HLM and photocatalytic methods with the use of UHPLC-MS/MS. in Molecules
MDPI AG., 25(6).
https://doi.org/10.3390/molecules25061367

Gawlik M, Savić V, Jovanović M, Skibiński R. Mimicking of phase I metabolism reactions of molindone by HLM and photocatalytic methods with the use of UHPLC-MS/MS. in Molecules. 2020;25(6).
doi:10.3390/molecules25061367 .

Gawlik, Maciej, Savić, Vladimir, Jovanović, Miloš, Skibiński, Robert, "Mimicking of phase I metabolism reactions of molindone by HLM and photocatalytic methods with the use of UHPLC-MS/MS" in Molecules, 25, no. 6 (2020),
https://doi.org/10.3390/molecules25061367 . .

TY  - CONF
AU  - Simić, Milena
AU  - Micić, Nikola
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Tasić, Gordana
AU  - Jovanović, Miloš
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5384
AB  - Tetracyclic octahydro-dipyrroloquinoline architecture is not commonly found in natural
products but some of them such as Incargranine B isolated from Incarvillea mairei var.
grandiflora and seneciobipyrrolidine isolated from Senecio scandens are derivatives of this
heterocycle [1-3], Figure 1. We envisaged potential synthetic pathway for this skeleton
based around two key steps: (3+2) dipolar cycloaddition of azomethine ylides and
unsaturated ketone and intramolecular Cu (I)-catalyzed amination to form the core
structure (Scheme 1). Creation of several chiral atoms during this process prompted careful
structural examination in order to establish correct stereochemistry and correlate it with
the structure of natural products.
PB  - Bruker BioSpin
C3  - 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts
T1  - Structural studies of model system for seneciobipyrrolidine skeleton synthesis
SP  - 52
EP  - 52
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5384
ER  - 

@conference{
author = "Simić, Milena and Micić, Nikola and Petković, Miloš and Jovanović, Predrag and Tasić, Gordana and Jovanović, Miloš and Savić, Vladimir",
year = "2019",
abstract = "Tetracyclic octahydro-dipyrroloquinoline architecture is not commonly found in natural
products but some of them such as Incargranine B isolated from Incarvillea mairei var.
grandiflora and seneciobipyrrolidine isolated from Senecio scandens are derivatives of this
heterocycle [1-3], Figure 1. We envisaged potential synthetic pathway for this skeleton
based around two key steps: (3+2) dipolar cycloaddition of azomethine ylides and
unsaturated ketone and intramolecular Cu (I)-catalyzed amination to form the core
structure (Scheme 1). Creation of several chiral atoms during this process prompted careful
structural examination in order to establish correct stereochemistry and correlate it with
the structure of natural products.",
publisher = "Bruker BioSpin",
journal = "21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts",
title = "Structural studies of model system for seneciobipyrrolidine skeleton synthesis",
pages = "52-52",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5384"
}

Simić, M., Micić, N., Petković, M., Jovanović, P., Tasić, G., Jovanović, M.,& Savić, V.. (2019). Structural studies of model system for seneciobipyrrolidine skeleton synthesis. in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts
Bruker BioSpin., 52-52.
https://hdl.handle.net/21.15107/rcub_farfar_5384

Simić M, Micić N, Petković M, Jovanović P, Tasić G, Jovanović M, Savić V. Structural studies of model system for seneciobipyrrolidine skeleton synthesis. in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts. 2019;:52-52.
https://hdl.handle.net/21.15107/rcub_farfar_5384 .

Simić, Milena, Micić, Nikola, Petković, Miloš, Jovanović, Predrag, Tasić, Gordana, Jovanović, Miloš, Savić, Vladimir, "Structural studies of model system for seneciobipyrrolidine skeleton synthesis" in 21st Central European NMR Symposium & Bruker Users Meeting, September 4-5, 2019 Belgrade, Serbia, Book of Abstracts (2019):52-52,
https://hdl.handle.net/21.15107/rcub_farfar_5384 .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Crnogorac, Marija Dj.
AU  - Žižak, Željko
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5329
AB  - A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals
VL  - 2019
IS  - 29
SP  - 4701
EP  - 4709
DO  - 10.1002/ejoc.201900672
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena and Jovanović, Miloš and Tasić, Gordana and Crnogorac, Marija Dj. and Žižak, Željko and Savić, Vladimir",
year = "2019",
abstract = "A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals",
volume = "2019",
number = "29",
pages = "4701-4709",
doi = "10.1002/ejoc.201900672"
}

Jovanović, P., Petković, M., Simić, M., Jovanović, M., Tasić, G., Crnogorac, M. Dj., Žižak, Ž.,& Savić, V.. (2019). Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2019(29), 4701-4709.
https://doi.org/10.1002/ejoc.201900672

Jovanović P, Petković M, Simić M, Jovanović M, Tasić G, Crnogorac MD, Žižak Ž, Savić V. Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry. 2019;2019(29):4701-4709.
doi:10.1002/ejoc.201900672 .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, Jovanović, Miloš, Tasić, Gordana, Crnogorac, Marija Dj., Žižak, Željko, Savić, Vladimir, "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals" in European Journal of Organic Chemistry, 2019, no. 29 (2019):4701-4709,
https://doi.org/10.1002/ejoc.201900672 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Radivojević, Jelena
AU  - O'Connor, Kevin
AU  - Blagojević, Stevan
AU  - Begović, Biljana
AU  - Lukić, Vera
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3335
AB  - Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.
PB  - Academic Press Inc Elsevier Science, San Diego
T2  - Bioorganic Chemistry
T1  - Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans
VL  - 87
SP  - 209
EP  - 217
DO  - 10.1016/j.bioorg.2019.03.023
ER  - 

@article{
author = "Jovanović, Miloš and Radivojević, Jelena and O'Connor, Kevin and Blagojević, Stevan and Begović, Biljana and Lukić, Vera and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2019",
abstract = "Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.",
publisher = "Academic Press Inc Elsevier Science, San Diego",
journal = "Bioorganic Chemistry",
title = "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans",
volume = "87",
pages = "209-217",
doi = "10.1016/j.bioorg.2019.03.023"
}

Jovanović, M., Radivojević, J., O'Connor, K., Blagojević, S., Begović, B., Lukić, V., Nikodinović-Runić, J.,& Savić, V.. (2019). Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry
Academic Press Inc Elsevier Science, San Diego., 87, 209-217.
https://doi.org/10.1016/j.bioorg.2019.03.023

Jovanović M, Radivojević J, O'Connor K, Blagojević S, Begović B, Lukić V, Nikodinović-Runić J, Savić V. Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry. 2019;87:209-217.
doi:10.1016/j.bioorg.2019.03.023 .

Jovanović, Miloš, Radivojević, Jelena, O'Connor, Kevin, Blagojević, Stevan, Begović, Biljana, Lukić, Vera, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans" in Bioorganic Chemistry, 87 (2019):209-217,
https://doi.org/10.1016/j.bioorg.2019.03.023 . .

TY  - JOUR
AU  - Anđelković, Milena
AU  - Buha-Đorđević, Aleksandra
AU  - Antonijević, Evica
AU  - Antonijević, Biljana
AU  - Stanić, Momcilo
AU  - Kotur-Stevuljević, Jelena
AU  - Spasojević-Kalimanovska, Vesna
AU  - Jovanović, Miloš
AU  - Boricić, Novica
AU  - Wallace, David
AU  - Bulat, Zorica
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3301
AB  - Background: Cadmium and lead are widespread and non-biodegradable pollutants of great concern to human health. In real life scenarios, we are exposed to mixtures of chemicals rather than single chemicals, and it is therefore of paramount importance to assess their toxicity. In this study, we investigated the toxicity of Cd and Pb alone and as a mixture in an animal model of acute exposure. Methods: Experimental groups received a single treatment of aqueous solution of Cd-chloride (15 and 30 mg/kg body weight (b.w.) and Pb-acetate (150 mg/kg b.w.), while the mixture group received 15 mg Cd/kg b.w. and 150 mg Pb/kg b.w. Toxic effects of individual metals and their mixture were investigated on hematological and biochemical parameters, and the redox status in the plasma, liver, and kidneys of treated Wistar rats. Results: Tissue-specific changes were recorded in various parameters of oxidative damage, while the accumulation of metals in tissues accompanied the disturbances of both hematological and biochemical parameters. It was observed that the level of toxic metals in tissues had a different distribution pattern after mixture and single exposure. Conclusions: Comprehensive observations suggest that exposure to Cd and Pb mixtures produces more pronounced effects compared to the response observed after exposure to single metal solutions. However, further research is needed to confirm toxicokinetic or toxicodynamic interactions between these two toxic metals in the organisms.
PB  - MDPI, Basel
T2  - International Journal of Environmental Research and Public Health
T1  - Toxic Effect of Acute Cadmium and Lead Exposure in Rat Blood, Liver, and Kidney
VL  - 16
IS  - 2
DO  - 10.3390/ijerph16020274
ER  - 

@article{
author = "Anđelković, Milena and Buha-Đorđević, Aleksandra and Antonijević, Evica and Antonijević, Biljana and Stanić, Momcilo and Kotur-Stevuljević, Jelena and Spasojević-Kalimanovska, Vesna and Jovanović, Miloš and Boricić, Novica and Wallace, David and Bulat, Zorica",
year = "2019",
abstract = "Background: Cadmium and lead are widespread and non-biodegradable pollutants of great concern to human health. In real life scenarios, we are exposed to mixtures of chemicals rather than single chemicals, and it is therefore of paramount importance to assess their toxicity. In this study, we investigated the toxicity of Cd and Pb alone and as a mixture in an animal model of acute exposure. Methods: Experimental groups received a single treatment of aqueous solution of Cd-chloride (15 and 30 mg/kg body weight (b.w.) and Pb-acetate (150 mg/kg b.w.), while the mixture group received 15 mg Cd/kg b.w. and 150 mg Pb/kg b.w. Toxic effects of individual metals and their mixture were investigated on hematological and biochemical parameters, and the redox status in the plasma, liver, and kidneys of treated Wistar rats. Results: Tissue-specific changes were recorded in various parameters of oxidative damage, while the accumulation of metals in tissues accompanied the disturbances of both hematological and biochemical parameters. It was observed that the level of toxic metals in tissues had a different distribution pattern after mixture and single exposure. Conclusions: Comprehensive observations suggest that exposure to Cd and Pb mixtures produces more pronounced effects compared to the response observed after exposure to single metal solutions. However, further research is needed to confirm toxicokinetic or toxicodynamic interactions between these two toxic metals in the organisms.",
publisher = "MDPI, Basel",
journal = "International Journal of Environmental Research and Public Health",
title = "Toxic Effect of Acute Cadmium and Lead Exposure in Rat Blood, Liver, and Kidney",
volume = "16",
number = "2",
doi = "10.3390/ijerph16020274"
}

Anđelković, M., Buha-Đorđević, A., Antonijević, E., Antonijević, B., Stanić, M., Kotur-Stevuljević, J., Spasojević-Kalimanovska, V., Jovanović, M., Boricić, N., Wallace, D.,& Bulat, Z.. (2019). Toxic Effect of Acute Cadmium and Lead Exposure in Rat Blood, Liver, and Kidney. in International Journal of Environmental Research and Public Health
MDPI, Basel., 16(2).
https://doi.org/10.3390/ijerph16020274

Anđelković M, Buha-Đorđević A, Antonijević E, Antonijević B, Stanić M, Kotur-Stevuljević J, Spasojević-Kalimanovska V, Jovanović M, Boricić N, Wallace D, Bulat Z. Toxic Effect of Acute Cadmium and Lead Exposure in Rat Blood, Liver, and Kidney. in International Journal of Environmental Research and Public Health. 2019;16(2).
doi:10.3390/ijerph16020274 .

Anđelković, Milena, Buha-Đorđević, Aleksandra, Antonijević, Evica, Antonijević, Biljana, Stanić, Momcilo, Kotur-Stevuljević, Jelena, Spasojević-Kalimanovska, Vesna, Jovanović, Miloš, Boricić, Novica, Wallace, David, Bulat, Zorica, "Toxic Effect of Acute Cadmium and Lead Exposure in Rat Blood, Liver, and Kidney" in International Journal of Environmental Research and Public Health, 16, no. 2 (2019),
https://doi.org/10.3390/ijerph16020274 . .

TY  - CONF
AU  - Jovanović, Predrag
AU  - Obradović, Dragiša
AU  - Tasić, Gordana
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Petković, Miloš
AU  - Savić, Vladimir
PY  - 2018
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5392
AB  - U ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje visoko
funkcionalizovanih ketona polazeći iz monosaharidnih derivata. Primenom Hekove reakcije1
na glikale i naknadnim otvaranjem dihidropiranskog prstena u prisustvu bor-trifluorida
dobijaju se hiralni polifunkcionalizovani ketoni koji mogu biti korisna polazna jedinjenja u
sintezi složenih molekula.
AB  - In this report we describe the reaction sequence for the synthesis of highly functionalised
ketones, starting from monosaccharide derivatives. Heck reaction is utilised to derivatise
glycals followed by dihydropyran ring opening in the presence of boron trifluoride diethyl
etherate. This gives access to polyfunctionalized ketones which can be useful starting
compounds in the synthesis of complex molecules.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija
T1  - Od monosaharida do polifunkcionalizovanih ketona
T1  - From monosaharids to polyfunctionalised ketones
SP  - 89
EP  - 89
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5392
ER  - 

@conference{
author = "Jovanović, Predrag and Obradović, Dragiša and Tasić, Gordana and Simić, Milena and Jovanović, Miloš and Petković, Miloš and Savić, Vladimir",
year = "2018",
abstract = "U ovoj studiji prikazana je reakciona sekvenca koja omogućuje dobijanje visoko
funkcionalizovanih ketona polazeći iz monosaharidnih derivata. Primenom Hekove reakcije1
na glikale i naknadnim otvaranjem dihidropiranskog prstena u prisustvu bor-trifluorida
dobijaju se hiralni polifunkcionalizovani ketoni koji mogu biti korisna polazna jedinjenja u
sintezi složenih molekula., In this report we describe the reaction sequence for the synthesis of highly functionalised
ketones, starting from monosaccharide derivatives. Heck reaction is utilised to derivatise
glycals followed by dihydropyran ring opening in the presence of boron trifluoride diethyl
etherate. This gives access to polyfunctionalized ketones which can be useful starting
compounds in the synthesis of complex molecules.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija",
title = "Od monosaharida do polifunkcionalizovanih ketona, From monosaharids to polyfunctionalised ketones",
pages = "89-89",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5392"
}

Jovanović, P., Obradović, D., Tasić, G., Simić, M., Jovanović, M., Petković, M.,& Savić, V.. (2018). Od monosaharida do polifunkcionalizovanih ketona. in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija
Srpsko hemijsko društvo, Beograd., 89-89.
https://hdl.handle.net/21.15107/rcub_farfar_5392

Jovanović P, Obradović D, Tasić G, Simić M, Jovanović M, Petković M, Savić V. Od monosaharida do polifunkcionalizovanih ketona. in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija. 2018;:89-89.
https://hdl.handle.net/21.15107/rcub_farfar_5392 .

Jovanović, Predrag, Obradović, Dragiša, Tasić, Gordana, Simić, Milena, Jovanović, Miloš, Petković, Miloš, Savić, Vladimir, "Od monosaharida do polifunkcionalizovanih ketona" in 55. Savetovanje Srpskog hemijskog društva.  Kratki izvodi radova, 8. i 9. juni 2018, Novi Sad, Srbija (2018):89-89,
https://hdl.handle.net/21.15107/rcub_farfar_5392 .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Petković, Miloš
AU  - Jovanović, Miloš
AU  - Milivojević, Dušan
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
AU  - Senerović, Lidija
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2858
AB  - A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.
PB  - Frontiers Media Sa, Lausanne
T2  - Frontiers in Microbiology
T1  - Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives
VL  - 8
DO  - 10.3389/fmicb.2017.02454
ER  - 

@article{
author = "Aleksić, Ivana and Petković, Miloš and Jovanović, Miloš and Milivojević, Dušan and Vasiljević, Branka and Nikodinović-Runić, Jasmina and Senerović, Lidija",
year = "2017",
abstract = "A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.",
publisher = "Frontiers Media Sa, Lausanne",
journal = "Frontiers in Microbiology",
title = "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives",
volume = "8",
doi = "10.3389/fmicb.2017.02454"
}

Aleksić, I., Petković, M., Jovanović, M., Milivojević, D., Vasiljević, B., Nikodinović-Runić, J.,& Senerović, L.. (2017). Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology
Frontiers Media Sa, Lausanne., 8.
https://doi.org/10.3389/fmicb.2017.02454

Aleksić I, Petković M, Jovanović M, Milivojević D, Vasiljević B, Nikodinović-Runić J, Senerović L. Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology. 2017;8.
doi:10.3389/fmicb.2017.02454 .

Aleksić, Ivana, Petković, Miloš, Jovanović, Miloš, Milivojević, Dušan, Vasiljević, Branka, Nikodinović-Runić, Jasmina, Senerović, Lidija, "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives" in Frontiers in Microbiology, 8 (2017),
https://doi.org/10.3389/fmicb.2017.02454 . .