Šmit, Biljana

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  • Šmit, Biljana (2)

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Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity

Jovanović-Stević, Snežana; Radisavljević, Snežana; Scheurer, Andreas; Ćoćić, Dušan; Šmit, Biljana; Petković, Marijana; Živanović, Marko N.; Virijević, Katarina; Petrović, Biljana

(2021)

TY  - JOUR
AU  - Jovanović-Stević, Snežana
AU  - Radisavljević, Snežana
AU  - Scheurer, Andreas
AU  - Ćoćić, Dušan
AU  - Šmit, Biljana
AU  - Petković, Marijana
AU  - Živanović, Marko N.
AU  - Virijević, Katarina
AU  - Petrović, Biljana
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/13318
AB  - Four new complexes of Pt(II) and Pd(II), [Pd(L1)Cl]Cl 1, [Pd(L2)Cl]Cl 2, [Pt(L1)Cl]Cl 3 and [Pt(L2)Cl]Cl 4 (where L1 = 2,6-bis(5,6-diphenyl-1,2,4-triazin-3-yl)pyridine and L2 = 2,6-bis(5,6-dipropyl-1,2,4-triazin-3-yl)pyridine), were synthesized. Characterization of the complexes was performed using elemental analysis, IR, 1H NMR spectroscopy and MALDI-TOF mass spectrometry. The substitution reactions of 1-4 complexes with L-methionine (L-met), L-cysteine (L-cys) and guanosine-5'-monophosphate (5'-GMP), were studied spectrophotometrically at physiological conditions. Complexes with ligand L1 (1 or 3) were more reactive than those with ligand L2 (2 or 4) by a factor ranging up to 1.57 and 3.71, respectively. The order of reactivity of the nucleophiles was: L-met > L-cys > 5'-GMP. The interactions of complexes with calf thymus-DNA (CT-DNA) and human serum albumin (HSA) were studied by Uv-Vis absorption and fluorescence emission spectroscopy. Competitive binding studies with intercalative agent ethidium bromide (EB) and minor groove binder Hoechst 33258 were performed as well. All studied complexes can interact with DNA through the intercalation and minor groove binding, where the latter was preferred. The binding constants (103 and 104 M-1) for the interaction of complexes with HSA indicate the moderate binding affinity of complexes 1-4 to protein. The trends in the experimental results of binding studies between complexes 3 and 4 with DNA and HSA were compared to those obtained from the molecular docking study. Biological evaluation of cytotoxicity of 1 and 2 on HCT-116 and MDA-MB-231 cell lines showed significant cytotoxic and prooxidative character, while 2 also exerted extraordinary selectivity towards colon cancer in comparison to breast cancer cells. The nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity of bis(triazinyl)pyridine complexes of Pt(II) and Pd(II) were studied.
T2  - JBIC Journal of Biological Inorganic Chemistry
T1  - Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity
VL  - 26
IS  - 5
SP  - 625
EP  - 637
DO  - 10.1007/s00775-021-01879-3
ER  - 
@article{
author = "Jovanović-Stević, Snežana and Radisavljević, Snežana and Scheurer, Andreas and Ćoćić, Dušan and Šmit, Biljana and Petković, Marijana and Živanović, Marko N. and Virijević, Katarina and Petrović, Biljana",
year = "2021",
abstract = "Four new complexes of Pt(II) and Pd(II), [Pd(L1)Cl]Cl 1, [Pd(L2)Cl]Cl 2, [Pt(L1)Cl]Cl 3 and [Pt(L2)Cl]Cl 4 (where L1 = 2,6-bis(5,6-diphenyl-1,2,4-triazin-3-yl)pyridine and L2 = 2,6-bis(5,6-dipropyl-1,2,4-triazin-3-yl)pyridine), were synthesized. Characterization of the complexes was performed using elemental analysis, IR, 1H NMR spectroscopy and MALDI-TOF mass spectrometry. The substitution reactions of 1-4 complexes with L-methionine (L-met), L-cysteine (L-cys) and guanosine-5'-monophosphate (5'-GMP), were studied spectrophotometrically at physiological conditions. Complexes with ligand L1 (1 or 3) were more reactive than those with ligand L2 (2 or 4) by a factor ranging up to 1.57 and 3.71, respectively. The order of reactivity of the nucleophiles was: L-met > L-cys > 5'-GMP. The interactions of complexes with calf thymus-DNA (CT-DNA) and human serum albumin (HSA) were studied by Uv-Vis absorption and fluorescence emission spectroscopy. Competitive binding studies with intercalative agent ethidium bromide (EB) and minor groove binder Hoechst 33258 were performed as well. All studied complexes can interact with DNA through the intercalation and minor groove binding, where the latter was preferred. The binding constants (103 and 104 M-1) for the interaction of complexes with HSA indicate the moderate binding affinity of complexes 1-4 to protein. The trends in the experimental results of binding studies between complexes 3 and 4 with DNA and HSA were compared to those obtained from the molecular docking study. Biological evaluation of cytotoxicity of 1 and 2 on HCT-116 and MDA-MB-231 cell lines showed significant cytotoxic and prooxidative character, while 2 also exerted extraordinary selectivity towards colon cancer in comparison to breast cancer cells. The nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity of bis(triazinyl)pyridine complexes of Pt(II) and Pd(II) were studied.",
journal = "JBIC Journal of Biological Inorganic Chemistry",
title = "Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity",
volume = "26",
number = "5",
pages = "625-637",
doi = "10.1007/s00775-021-01879-3"
}
Jovanović-Stević, S., Radisavljević, S., Scheurer, A., Ćoćić, D., Šmit, B., Petković, M., Živanović, M. N., Virijević, K.,& Petrović, B.. (2021). Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity. in JBIC Journal of Biological Inorganic Chemistry, 26(5), 625-637.
https://doi.org/10.1007/s00775-021-01879-3
Jovanović-Stević S, Radisavljević S, Scheurer A, Ćoćić D, Šmit B, Petković M, Živanović MN, Virijević K, Petrović B. Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity. in JBIC Journal of Biological Inorganic Chemistry. 2021;26(5):625-637.
doi:10.1007/s00775-021-01879-3 .
Jovanović-Stević, Snežana, Radisavljević, Snežana, Scheurer, Andreas, Ćoćić, Dušan, Šmit, Biljana, Petković, Marijana, Živanović, Marko N., Virijević, Katarina, Petrović, Biljana, "Bis(triazinyl)pyridine complexes of Pt(II) and Pd(II): studies of the nucleophilic substitution reactions, DNA/HSA interactions, molecular docking and biological activity" in JBIC Journal of Biological Inorganic Chemistry, 26, no. 5 (2021):625-637,
https://doi.org/10.1007/s00775-021-01879-3 . .
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Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes

Radisavljević, Snežana; Ćoćić, Dušan; Jovanović, Snežana; Šmit, Biljana; Petković, Marijana; Milivojević, Nevena; Planojević, Nevena; Marković, Snežana D.; Petrović, Biljana V.

(2019)

TY  - JOUR
AU  - Radisavljević, Snežana
AU  - Ćoćić, Dušan
AU  - Jovanović, Snežana
AU  - Šmit, Biljana
AU  - Petković, Marijana
AU  - Milivojević, Nevena
AU  - Planojević, Nevena
AU  - Marković, Snežana D.
AU  - Petrović, Biljana V.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8592
AB  - Abstract: In this study, we have synthesized a series of dinuclear and trinuclear gold(III) complexes of the general formula [Au2(N–N)Cl6] (1–3) for dinuclear and [Au3(N–N)2Cl8]+ (4–6) for trinuclear compounds, respectively, in which N–N is a bidentate ligand (1,4-diaminobutane; 1,6-diaminohexane or 1,8-diaminooctane). These complexes were characterized by elemental analysis, molar conductivity, and spectroscopic techniques (IR, UV–Vis, 1H NMR, ESI–MS). We performed DFT calculations to get insight into the geometry of the studies complexes. DNA-binding studies were performed by UV–Vis spectrophotometry and fluorescence spectroscopy. The results of competitive reactions between gold(III) complexes and ethidium bromide (EB) towards DNA have shown that selected complexes can displace EB from DNA-EB adduct. In addition, these experiments confirm that polynuclear gold(III) complexes interact with DNA covalently or via intercalation. Furthermore, high values of binding constants of gold(III) complexes towards bovine serum albumin (BSA) protein indicate good binding affinity. In addition, redox stability of complexes in the presence of DNA/BSA was confirmed by cyclic voltammetry. Results of the interactions between gold(III) complexes with DNA/BSA were discussed in reference to molecular docking data obtain by Molegro virtual docker. The cytotoxic activity of synthesized gold(III) complexes was evaluated on human breast cancer cell line (MDA-MB-231), human colorectal cancer cell line (HCT-116), and normal human lung fibroblast cell line (MRC-5). All complexes dose-dependently reduced cancer and normal cells viabilities, with significant cytotoxic effects (IC50 < 25 μM) for trinuclear gold(III) complexes (4, 5) on HCT-116 cells. Graphic abstract: [Figure not available: see fulltext.].
T2  - JBIC Journal of Biological Inorganic Chemistry
T1  - Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes
VL  - 24
IS  - 7
SP  - 1057
EP  - 1076
DO  - 10.1007/s00775-019-01716-8
ER  - 
@article{
author = "Radisavljević, Snežana and Ćoćić, Dušan and Jovanović, Snežana and Šmit, Biljana and Petković, Marijana and Milivojević, Nevena and Planojević, Nevena and Marković, Snežana D. and Petrović, Biljana V.",
year = "2019",
abstract = "Abstract: In this study, we have synthesized a series of dinuclear and trinuclear gold(III) complexes of the general formula [Au2(N–N)Cl6] (1–3) for dinuclear and [Au3(N–N)2Cl8]+ (4–6) for trinuclear compounds, respectively, in which N–N is a bidentate ligand (1,4-diaminobutane; 1,6-diaminohexane or 1,8-diaminooctane). These complexes were characterized by elemental analysis, molar conductivity, and spectroscopic techniques (IR, UV–Vis, 1H NMR, ESI–MS). We performed DFT calculations to get insight into the geometry of the studies complexes. DNA-binding studies were performed by UV–Vis spectrophotometry and fluorescence spectroscopy. The results of competitive reactions between gold(III) complexes and ethidium bromide (EB) towards DNA have shown that selected complexes can displace EB from DNA-EB adduct. In addition, these experiments confirm that polynuclear gold(III) complexes interact with DNA covalently or via intercalation. Furthermore, high values of binding constants of gold(III) complexes towards bovine serum albumin (BSA) protein indicate good binding affinity. In addition, redox stability of complexes in the presence of DNA/BSA was confirmed by cyclic voltammetry. Results of the interactions between gold(III) complexes with DNA/BSA were discussed in reference to molecular docking data obtain by Molegro virtual docker. The cytotoxic activity of synthesized gold(III) complexes was evaluated on human breast cancer cell line (MDA-MB-231), human colorectal cancer cell line (HCT-116), and normal human lung fibroblast cell line (MRC-5). All complexes dose-dependently reduced cancer and normal cells viabilities, with significant cytotoxic effects (IC50 < 25 μM) for trinuclear gold(III) complexes (4, 5) on HCT-116 cells. Graphic abstract: [Figure not available: see fulltext.].",
journal = "JBIC Journal of Biological Inorganic Chemistry",
title = "Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes",
volume = "24",
number = "7",
pages = "1057-1076",
doi = "10.1007/s00775-019-01716-8"
}
Radisavljević, S., Ćoćić, D., Jovanović, S., Šmit, B., Petković, M., Milivojević, N., Planojević, N., Marković, S. D.,& Petrović, B. V.. (2019). Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes. in JBIC Journal of Biological Inorganic Chemistry, 24(7), 1057-1076.
https://doi.org/10.1007/s00775-019-01716-8
Radisavljević S, Ćoćić D, Jovanović S, Šmit B, Petković M, Milivojević N, Planojević N, Marković SD, Petrović BV. Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes. in JBIC Journal of Biological Inorganic Chemistry. 2019;24(7):1057-1076.
doi:10.1007/s00775-019-01716-8 .
Radisavljević, Snežana, Ćoćić, Dušan, Jovanović, Snežana, Šmit, Biljana, Petković, Marijana, Milivojević, Nevena, Planojević, Nevena, Marković, Snežana D., Petrović, Biljana V., "Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes" in JBIC Journal of Biological Inorganic Chemistry, 24, no. 7 (2019):1057-1076,
https://doi.org/10.1007/s00775-019-01716-8 . .
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