TY  - JOUR
AU  - Mijatović, Aleksandar
AU  - Cakovic, Angelina
AU  - Lolić, Aleksandar
AU  - Sretenovic, Snezana
AU  - Zivanovic, Marko
AU  - Petrović, Biljana
AU  - Bogojeski, Jovana
AU  - Seklic, Dragana
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6458
AB  - Three Schiff base Cu(II) complexes, (N,N’-bis(acetylacetone)­propyl­enediimine)copper(II) complex, [Cu(acac2pn)] (1), (N,N'-bis-(ben­zoyl­acet­one)propylenediimine)copper(II) complex, [Cu(phacac2pn)] (2) and (N,N’-bis-(trifluoroacetylacetone)propylenediimine)­copper(II) complex, [Cu(tfacac2pn)] (3), were used to investigate the interactions with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) using the electronic absorption and spectro­scopic fluorescence methods. UV–Vis absorption studies showed that studied complexes interact with DNA molecule and exhibit moderate binding affinity. Fluorescence studies of complexes 1–3 also showed a possibility for DNA int­ercalation as well as a relatively high binding ability toward BSA. Among the tested complexes, the highest affinity for DNA and BSA molecules was shown by complex 1. Cytotoxic analyses, performed on human colorectal carcinoma HCT-116 and healthy lung fibroblast MRC-5 cell lines, showed that complex 2 exhibited activity on both cell lines, while complexes 1 and 3 did not show any activity.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O-Schiff base copper(II) complexes: Scientific paper
VL  - 88
IS  - 12
SP  - 1307
EP  - 1317
DO  - 10.2298/JSC230614063M
ER  - 

@article{
author = "Mijatović, Aleksandar and Cakovic, Angelina and Lolić, Aleksandar and Sretenovic, Snezana and Zivanovic, Marko and Petrović, Biljana and Bogojeski, Jovana and Seklic, Dragana",
year = "2023",
abstract = "Three Schiff base Cu(II) complexes, (N,N’-bis(acetylacetone)­propyl­enediimine)copper(II) complex, [Cu(acac2pn)] (1), (N,N'-bis-(ben­zoyl­acet­one)propylenediimine)copper(II) complex, [Cu(phacac2pn)] (2) and (N,N’-bis-(trifluoroacetylacetone)propylenediimine)­copper(II) complex, [Cu(tfacac2pn)] (3), were used to investigate the interactions with calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) using the electronic absorption and spectro­scopic fluorescence methods. UV–Vis absorption studies showed that studied complexes interact with DNA molecule and exhibit moderate binding affinity. Fluorescence studies of complexes 1–3 also showed a possibility for DNA int­ercalation as well as a relatively high binding ability toward BSA. Among the tested complexes, the highest affinity for DNA and BSA molecules was shown by complex 1. Cytotoxic analyses, performed on human colorectal carcinoma HCT-116 and healthy lung fibroblast MRC-5 cell lines, showed that complex 2 exhibited activity on both cell lines, while complexes 1 and 3 did not show any activity.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O-Schiff base copper(II) complexes: Scientific paper",
volume = "88",
number = "12",
pages = "1307-1317",
doi = "10.2298/JSC230614063M"
}

Mijatović, A., Cakovic, A., Lolić, A., Sretenovic, S., Zivanovic, M., Petrović, B., Bogojeski, J.,& Seklic, D.. (2023). DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O-Schiff base copper(II) complexes: Scientific paper. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 88(12), 1307-1317.
https://doi.org/10.2298/JSC230614063M

Mijatović A, Cakovic A, Lolić A, Sretenovic S, Zivanovic M, Petrović B, Bogojeski J, Seklic D. DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O-Schiff base copper(II) complexes: Scientific paper. in Journal of the Serbian Chemical Society. 2023;88(12):1307-1317.
doi:10.2298/JSC230614063M .

Mijatović, Aleksandar, Cakovic, Angelina, Lolić, Aleksandar, Sretenovic, Snezana, Zivanovic, Marko, Petrović, Biljana, Bogojeski, Jovana, Seklic, Dragana, "DNA/BSA interactions and cytotoxic studies of tetradentate N,N,O,O-Schiff base copper(II) complexes: Scientific paper" in Journal of the Serbian Chemical Society, 88, no. 12 (2023):1307-1317,
https://doi.org/10.2298/JSC230614063M . .

TY  - JOUR
AU  - Međedović, Milica
AU  - Mijatović, Aleksandar
AU  - Baošić, Rada
AU  - Lazić, Dejan
AU  - Milanović, Žiko
AU  - Marković, Zoran
AU  - Milovanović, Jelena
AU  - Arsenijević, Dragana
AU  - Stojanović, Bojana
AU  - Arsenijević, Miloš
AU  - Milovanović, Marija
AU  - Petrović, Biljana
AU  - Rilak Simović, Ana
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6353
AB  - In order to discover new anticancer drugs, novel ruthenium(III) complexes [Ru(L)Cl(H2O)], where L is tetradentate Schiff base bis(acetylacetone)ethylendiimine (acacen, 1), bis(benzoylacetone)ethylendiimine (bzacen, 2), (acetylacetone)(benzoylaceton)ethylendiimine (acacbzacen, 3), bis(acetylacetone)propylendiimine (acacpn, 4), bis(benzoylacetone)propylendiimine (bzacpn, 5) or (acetylacetone)(benzoylaceton)propylendiimine (acacbzacpn, 6), were synthesized. The complexes 1 – 6 were characterized by elemental analysis, molar conductometry, and by various spectroscopic techniques, such as UV–Vis, IR, EPR, and ESI-MS. Based on in vitro DNA/BSA experiments, complexes 2 (bzacen) and 5 (bzacpn) with two aromatic rings showed the highest DNA/BSA-activity, suggesting that the presence of the aromatic ring on the tetradentate Schiff base ligand contributes to increased activity. Moreover, these two compounds showed the highest cytotoxic effects toward human, A549 and murine LLC1 lung cancer cells. These complexes altered the ratio of anti- and pro-apoptotic molecules and induced apoptosis of A549 cells. Further, complexes 2 and 5 reduced the percentage of Mcl1 and Bcl2 expressing LLC1 cells, induced their apoptotic death and exerted an antiproliferative effect against LLC1. Finally, complex 5 reduced the volume of mouse primary heterotopic Lewis lung cancer, while complex 2 reduced the incidence and mean number of metastases per lung. Additionally, molecular docking with DNA revealed that the reduced number of aromatic rings or their absence causes lower intercalative properties of the complexes in order: 2 > 5 > 6 > 3 > 4 > 1. It was observed that conventional hydrogen bonds and hydrophobic interactions contribute to the stabilization of the structures of complex-DNA. A molecular docking study with BSA revealed a predominance of 1 – 6 in binding affinity to the active site III, a third D-shaped hydrophobic pocket within subdomain IB.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization, biomolecular interactions, molecular docking, and in vitro and in vivo anticancer activities of novel ruthenium(III) Schiff base complexes
VL  - 248
SP  - 112363
DO  - 10.1016/j.jinorgbio.2023.112363
ER  - 

@article{
author = "Međedović, Milica and Mijatović, Aleksandar and Baošić, Rada and Lazić, Dejan and Milanović, Žiko and Marković, Zoran and Milovanović, Jelena and Arsenijević, Dragana and Stojanović, Bojana and Arsenijević, Miloš and Milovanović, Marija and Petrović, Biljana and Rilak Simović, Ana",
year = "2023",
abstract = "In order to discover new anticancer drugs, novel ruthenium(III) complexes [Ru(L)Cl(H2O)], where L is tetradentate Schiff base bis(acetylacetone)ethylendiimine (acacen, 1), bis(benzoylacetone)ethylendiimine (bzacen, 2), (acetylacetone)(benzoylaceton)ethylendiimine (acacbzacen, 3), bis(acetylacetone)propylendiimine (acacpn, 4), bis(benzoylacetone)propylendiimine (bzacpn, 5) or (acetylacetone)(benzoylaceton)propylendiimine (acacbzacpn, 6), were synthesized. The complexes 1 – 6 were characterized by elemental analysis, molar conductometry, and by various spectroscopic techniques, such as UV–Vis, IR, EPR, and ESI-MS. Based on in vitro DNA/BSA experiments, complexes 2 (bzacen) and 5 (bzacpn) with two aromatic rings showed the highest DNA/BSA-activity, suggesting that the presence of the aromatic ring on the tetradentate Schiff base ligand contributes to increased activity. Moreover, these two compounds showed the highest cytotoxic effects toward human, A549 and murine LLC1 lung cancer cells. These complexes altered the ratio of anti- and pro-apoptotic molecules and induced apoptosis of A549 cells. Further, complexes 2 and 5 reduced the percentage of Mcl1 and Bcl2 expressing LLC1 cells, induced their apoptotic death and exerted an antiproliferative effect against LLC1. Finally, complex 5 reduced the volume of mouse primary heterotopic Lewis lung cancer, while complex 2 reduced the incidence and mean number of metastases per lung. Additionally, molecular docking with DNA revealed that the reduced number of aromatic rings or their absence causes lower intercalative properties of the complexes in order: 2 > 5 > 6 > 3 > 4 > 1. It was observed that conventional hydrogen bonds and hydrophobic interactions contribute to the stabilization of the structures of complex-DNA. A molecular docking study with BSA revealed a predominance of 1 – 6 in binding affinity to the active site III, a third D-shaped hydrophobic pocket within subdomain IB.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization, biomolecular interactions, molecular docking, and in vitro and in vivo anticancer activities of novel ruthenium(III) Schiff base complexes",
volume = "248",
pages = "112363",
doi = "10.1016/j.jinorgbio.2023.112363"
}

Međedović, M., Mijatović, A., Baošić, R., Lazić, D., Milanović, Ž., Marković, Z., Milovanović, J., Arsenijević, D., Stojanović, B., Arsenijević, M., Milovanović, M., Petrović, B.,& Rilak Simović, A.. (2023). Synthesis, characterization, biomolecular interactions, molecular docking, and in vitro and in vivo anticancer activities of novel ruthenium(III) Schiff base complexes. in Journal of Inorganic Biochemistry
Elsevier., 248, 112363.
https://doi.org/10.1016/j.jinorgbio.2023.112363

Međedović M, Mijatović A, Baošić R, Lazić D, Milanović Ž, Marković Z, Milovanović J, Arsenijević D, Stojanović B, Arsenijević M, Milovanović M, Petrović B, Rilak Simović A. Synthesis, characterization, biomolecular interactions, molecular docking, and in vitro and in vivo anticancer activities of novel ruthenium(III) Schiff base complexes. in Journal of Inorganic Biochemistry. 2023;248:112363.
doi:10.1016/j.jinorgbio.2023.112363 .

Međedović, Milica, Mijatović, Aleksandar, Baošić, Rada, Lazić, Dejan, Milanović, Žiko, Marković, Zoran, Milovanović, Jelena, Arsenijević, Dragana, Stojanović, Bojana, Arsenijević, Miloš, Milovanović, Marija, Petrović, Biljana, Rilak Simović, Ana, "Synthesis, characterization, biomolecular interactions, molecular docking, and in vitro and in vivo anticancer activities of novel ruthenium(III) Schiff base complexes" in Journal of Inorganic Biochemistry, 248 (2023):112363,
https://doi.org/10.1016/j.jinorgbio.2023.112363 . .

TY  - JOUR
AU  - Rilak, Ana
AU  - Petrović, Biljana
AU  - Grgurić-Šipka, Sanja
AU  - Tešić, Živoslav Lj.
AU  - Bugarcic, Zivadin D.
PY  - 2011
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1197
AB  - The reactions of ruthenium(II)-arene complex [Ru-II(eta(6)-p-cym)(pydc)Cl] (where p-cym = p-isopropyl toluene, pydc = 2,3-pyridinedicarboxylato) with biologically nitrogen-donor nucleophiles, such as guanosine-5'-monophosphate (5'-GMP), guanosine (Guo) and L-histidine (L-His) were studied by UV-Vis spectrophotometry and H-1 NMR spectroscopy. The reactions were studied at pH 2.5 and at 7.2. All reactions were followed under pseudo-first order conditions with large excess of the nucleophiles. The selected nucleophiles have a high affinity for Ru(II)-arene complex. The reactivity of the used ligands follow the same order at both pH values: Guo  gt  5'-GMP  gt  L-His, while the reactions at pH 7.2 are always faster. The negative entropies of activation (Delta S-not equal) support an associative mode of activation. However, the rate constants obtained by H-1 NMR at 295 K in D2O follow the same order of the ligand reactivity. The hydrolysis of the [Ru-II(eta(6)-p-cym)(pydc)Cl] complex was very fast and completed by the time the first spectrum was measured. Addition of excess of NaCl to equilibrium solutions reversed the hydrolysis. (C) 2011 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - Kinetics and mechanism of the reactions of Ru(II)-arene complex with some biologically relevant ligands
VL  - 30
IS  - 13
SP  - 2339
EP  - 2344
DO  - 10.1016/j.poly.2011.06.019
ER  - 

@article{
author = "Rilak, Ana and Petrović, Biljana and Grgurić-Šipka, Sanja and Tešić, Živoslav Lj. and Bugarcic, Zivadin D.",
year = "2011",
abstract = "The reactions of ruthenium(II)-arene complex [Ru-II(eta(6)-p-cym)(pydc)Cl] (where p-cym = p-isopropyl toluene, pydc = 2,3-pyridinedicarboxylato) with biologically nitrogen-donor nucleophiles, such as guanosine-5'-monophosphate (5'-GMP), guanosine (Guo) and L-histidine (L-His) were studied by UV-Vis spectrophotometry and H-1 NMR spectroscopy. The reactions were studied at pH 2.5 and at 7.2. All reactions were followed under pseudo-first order conditions with large excess of the nucleophiles. The selected nucleophiles have a high affinity for Ru(II)-arene complex. The reactivity of the used ligands follow the same order at both pH values: Guo  gt  5'-GMP  gt  L-His, while the reactions at pH 7.2 are always faster. The negative entropies of activation (Delta S-not equal) support an associative mode of activation. However, the rate constants obtained by H-1 NMR at 295 K in D2O follow the same order of the ligand reactivity. The hydrolysis of the [Ru-II(eta(6)-p-cym)(pydc)Cl] complex was very fast and completed by the time the first spectrum was measured. Addition of excess of NaCl to equilibrium solutions reversed the hydrolysis. (C) 2011 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "Kinetics and mechanism of the reactions of Ru(II)-arene complex with some biologically relevant ligands",
volume = "30",
number = "13",
pages = "2339-2344",
doi = "10.1016/j.poly.2011.06.019"
}

Rilak, A., Petrović, B., Grgurić-Šipka, S., Tešić, Ž. Lj.,& Bugarcic, Z. D.. (2011). Kinetics and mechanism of the reactions of Ru(II)-arene complex with some biologically relevant ligands. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 30(13), 2339-2344.
https://doi.org/10.1016/j.poly.2011.06.019

Rilak A, Petrović B, Grgurić-Šipka S, Tešić ŽL, Bugarcic ZD. Kinetics and mechanism of the reactions of Ru(II)-arene complex with some biologically relevant ligands. in Polyhedron. 2011;30(13):2339-2344.
doi:10.1016/j.poly.2011.06.019 .

Rilak, Ana, Petrović, Biljana, Grgurić-Šipka, Sanja, Tešić, Živoslav Lj., Bugarcic, Zivadin D., "Kinetics and mechanism of the reactions of Ru(II)-arene complex with some biologically relevant ligands" in Polyhedron, 30, no. 13 (2011):2339-2344,
https://doi.org/10.1016/j.poly.2011.06.019 . .