Milčić, Miloš

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orcid::0000-0002-0082-5278
  • Milčić, Miloš (2)

Author's Bibliography

Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins

Vitomirov, Teodora; Dimiza, Filitsa; Matić, Ivana Z.; Stanojković, Tatjana; Pirković, Andrea; Živković, Lada; Spremo-Potparević, Biljana; Novaković, Irena; Anđelković, Katarina; Milčić, Miloš; Psomas, George; Šumar Ristović, Maja

(Elsevier Inc., 2022)

TY  - JOUR
AU  - Vitomirov, Teodora
AU  - Dimiza, Filitsa
AU  - Matić, Ivana Z.
AU  - Stanojković, Tatjana
AU  - Pirković, Andrea
AU  - Živković, Lada
AU  - Spremo-Potparević, Biljana
AU  - Novaković, Irena
AU  - Anđelković, Katarina
AU  - Milčić, Miloš
AU  - Psomas, George
AU  - Šumar Ristović, Maja
PY  - 2022
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4248
AB  - In this article, cytotoxicity, the mechanisms of cytotoxic activity, genotoxicity, and interaction with DNA and proteins, of two Cu(II) complexes with a salicylaldehyde derivative (4-(diethylamino)salicylaldehyde) and α-diimine (2,2′-bipyridine (bipy) and 1,10-phenanthroline (phen)) are reported. Both Cu(II) complexes performed cytotoxic effects against all tested malignant cell lines. Complexes exerted highest cytotoxicity against HeLa and A375 malignant cell lines. The cytotoxic activity of Cu(II) complex with phen as a α-diimine co-ligand was significantly higher in comparison with cytotoxic activity of Cu(II) complex with bipy. Pretreatment with specific inhibitors of caspase-3, caspase-8 or caspase-9, in order to clear up the mode of cell death triggered by two Cu(II) complexes in HeLa cells, indicated the ability of these complexes to induce apoptosis through activation of target caspases. Cu(II)-phen complex exhibited significant antioxidant activity compared with Cu(II)-bipy complex, and showed a better effect on reducing intracellular ROS levels in HeLa cells. Tested complexes did not display genotoxic potential in human peripheral blood leucocytes, but exhibited an antigenotoxic effect in post-treatment, after H2O2 exposure. The study of the in vitro biological properties regarding their affinity towards CT (calf-thymus) DNA and serum albumins showed that the compounds can intercalate to CT DNA, and bind reversibly and tightly to the albumins. Molecular docking studies of the ability of compounds to bind to biomacromolecules are consistent with in vitro studies.
PB  - Elsevier Inc.
T2  - Journal of Inorganic Biochemistry
T1  - Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins
VL  - 235
DO  - 10.1016/j.jinorgbio.2022.111942
ER  - 
@article{
author = "Vitomirov, Teodora and Dimiza, Filitsa and Matić, Ivana Z. and Stanojković, Tatjana and Pirković, Andrea and Živković, Lada and Spremo-Potparević, Biljana and Novaković, Irena and Anđelković, Katarina and Milčić, Miloš and Psomas, George and Šumar Ristović, Maja",
year = "2022",
abstract = "In this article, cytotoxicity, the mechanisms of cytotoxic activity, genotoxicity, and interaction with DNA and proteins, of two Cu(II) complexes with a salicylaldehyde derivative (4-(diethylamino)salicylaldehyde) and α-diimine (2,2′-bipyridine (bipy) and 1,10-phenanthroline (phen)) are reported. Both Cu(II) complexes performed cytotoxic effects against all tested malignant cell lines. Complexes exerted highest cytotoxicity against HeLa and A375 malignant cell lines. The cytotoxic activity of Cu(II) complex with phen as a α-diimine co-ligand was significantly higher in comparison with cytotoxic activity of Cu(II) complex with bipy. Pretreatment with specific inhibitors of caspase-3, caspase-8 or caspase-9, in order to clear up the mode of cell death triggered by two Cu(II) complexes in HeLa cells, indicated the ability of these complexes to induce apoptosis through activation of target caspases. Cu(II)-phen complex exhibited significant antioxidant activity compared with Cu(II)-bipy complex, and showed a better effect on reducing intracellular ROS levels in HeLa cells. Tested complexes did not display genotoxic potential in human peripheral blood leucocytes, but exhibited an antigenotoxic effect in post-treatment, after H2O2 exposure. The study of the in vitro biological properties regarding their affinity towards CT (calf-thymus) DNA and serum albumins showed that the compounds can intercalate to CT DNA, and bind reversibly and tightly to the albumins. Molecular docking studies of the ability of compounds to bind to biomacromolecules are consistent with in vitro studies.",
publisher = "Elsevier Inc.",
journal = "Journal of Inorganic Biochemistry",
title = "Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins",
volume = "235",
doi = "10.1016/j.jinorgbio.2022.111942"
}
Vitomirov, T., Dimiza, F., Matić, I. Z., Stanojković, T., Pirković, A., Živković, L., Spremo-Potparević, B., Novaković, I., Anđelković, K., Milčić, M., Psomas, G.,& Šumar Ristović, M.. (2022). Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins. in Journal of Inorganic Biochemistry
Elsevier Inc.., 235.
https://doi.org/10.1016/j.jinorgbio.2022.111942
Vitomirov T, Dimiza F, Matić IZ, Stanojković T, Pirković A, Živković L, Spremo-Potparević B, Novaković I, Anđelković K, Milčić M, Psomas G, Šumar Ristović M. Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins. in Journal of Inorganic Biochemistry. 2022;235.
doi:10.1016/j.jinorgbio.2022.111942 .
Vitomirov, Teodora, Dimiza, Filitsa, Matić, Ivana Z., Stanojković, Tatjana, Pirković, Andrea, Živković, Lada, Spremo-Potparević, Biljana, Novaković, Irena, Anđelković, Katarina, Milčić, Miloš, Psomas, George, Šumar Ristović, Maja, "Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins" in Journal of Inorganic Biochemistry, 235 (2022),
https://doi.org/10.1016/j.jinorgbio.2022.111942 . .
7
7

Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60

Jakšić, Jovana; Mitrović, Aleksandra; Tokić-Vujošević, Zorana; Milčić, Miloš; Maslak, Veselin

(Royal Society of Chemistry, 2021)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Mitrović, Aleksandra
AU  - Tokić-Vujošević, Zorana
AU  - Milčić, Miloš
AU  - Maslak, Veselin
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3982
AB  - In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
VL  - 11
IS  - 47
SP  - 29426
EP  - 29432
DO  - 10.1039/d1ra03944j
ER  - 
@article{
author = "Jakšić, Jovana and Mitrović, Aleksandra and Tokić-Vujošević, Zorana and Milčić, Miloš and Maslak, Veselin",
year = "2021",
abstract = "In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60",
volume = "11",
number = "47",
pages = "29426-29432",
doi = "10.1039/d1ra03944j"
}
Jakšić, J., Mitrović, A., Tokić-Vujošević, Z., Milčić, M.,& Maslak, V.. (2021). Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances
Royal Society of Chemistry., 11(47), 29426-29432.
https://doi.org/10.1039/d1ra03944j
Jakšić J, Mitrović A, Tokić-Vujošević Z, Milčić M, Maslak V. Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances. 2021;11(47):29426-29432.
doi:10.1039/d1ra03944j .
Jakšić, Jovana, Mitrović, Aleksandra, Tokić-Vujošević, Zorana, Milčić, Miloš, Maslak, Veselin, "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60" in RSC Advances, 11, no. 47 (2021):29426-29432,
https://doi.org/10.1039/d1ra03944j . .
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