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Publikation

Pantelić, N.; Stanojković, T. P.; Zmejkovski, B. B.; Kaluđerović, G. N.; Sabo, T. J.; Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate Serb. J. Exp. Clin. Res. 18, 289-294, (2017) DOI: 10.1515/sjecr-2017-0067

Six gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate, general formula [AuCl2{(S,S)-R2eddch}]PF6, [(S,S)-eddch = (S,S)-ethylenediamine-N,N’-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am, 1–6, respectively], were tested against cancer cell lines such as human melanoma Fem-x, human colon carcinoma LS174T and non-small cell lung carcinoma A549 as well as a non-cancerous human embryonic lung fibroblasts MRC-5 using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with the aim of assessing in vitro antitumoral activity and selectivity. All investigated complexes showed lower cytotoxicity and better or similar selectivity in comparison to cisplatin, used as reference compound. Complex [AuCl2{(S,S)-(i-Am)2eddch}]PF6 (6) demonstrated the highest activity against Fem-x (IC50 = 14.98 ± 0.34 μM). Additionally, the same complex expressed 4.5 times higher selectivity than cisplatin.
Publikation

Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. ?.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N.; In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands J. Inorg. Biochem. 172, 55-66, (2017) DOI: 10.1016/j.jinorgbio.2017.04.001

Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R2eddl}]PF6 (R2eddl = O,O′-dialkyl-(S,S)-ethylenediamine-N,N′-di-2-(4-methyl)pentanoate, R = n-Pr, n-Bu, n-Pe, i-Bu; 1–4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N′-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04–6.51 μM). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
Publikation

Zmejkovski, B. B.; Pantelić, N.; Filipović, L.; Aranđelović, S.; Radulović, S.; Sabo, T. J.; Kaluđerović, G. N.; In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N’-di-2-propanoic Acid Anti-Cancer Agents Med. Chem. 17, 1136-1143, (2017) DOI: 10.2174/1871520616666161207155634

Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)2eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)2eddip = O,O’-diisoamyl-(S,S)-ethylenediamine-N,N’-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy and mass spectrometry.Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant 13C NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 μM), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.
Publikation

Pantelić, N.; Zmejkovski, B. B.; Marković, D. D.; Vujić, J. M.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N.; Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O′-Diethyl Ester of Ethylenediamine-N,N′-Di-2-(4-Methyl)Pentanoic Acid Metals 6, 226, (2016) DOI: 10.3390/met6090226

A novel gold(III) complex, [AuCl2{(S,S)-Et2eddl}]PF6, ((S,S)-Et2eddl = O,O′-diethyl ester of ethylenediamine-N,N′-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (1H and 13C), and 2D (H,H-COSY and H,H-NOESY) NMR spectroscopy, mass spectrometry, and elemental analysis. Density functional theory calculations confirmed that (R,R)-N,N′ diastereoisomer was energetically the most stable isomer. In vitro antitumor action of ligand precursor [(S,S)-H2Et2eddl]Cl2 and corresponding gold(III) complex was determined against tumor cell lines: human adenocarcinoma (HeLa), human colon carcinoma (LS174), human breast cancer (MCF7), non-small cell lung carcinoma cell line (A549), and non-cancerous cell line human embryonic lung fibroblast (MRC-5) using microculture tetrazolium test (MTT) assay. The results indicate that both ligand precursor and gold(III) complex have showed very good to moderate cytotoxic activity against all tested malignant cell lines. The highest activity was expressed by [AuCl2{(S,S)-Et2eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 ± 1.2 µM.
Publikation

Pantelić, N.; Stanojković, T. P.; Zmejkovski, B. B.; Sabo, T. J.; Kaluđerović, G. N.; In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N′-di-2-propanoic acid Eur. J. Med. Chem. 90, 766-774, (2015) DOI: 10.1016/j.ejmech.2014.12.019

Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R2eddip}]PF6, ((S,S)-eddip = (S,S)-ethylenediamine-N,N′-di-2-propanoate, R = n-Bu, n-Pe, i-Bu, i-Am, cPe; 1–5, respectively) were synthesized and characterized by UV/Vis, IR and NMR spectroscopy and mass spectrometry. DFT calculations indicated that (R,R)-N,N′-configuration diastereoisomers were the most stable for 1–5. 3 is stable in DMSO for at least 24 h, but immediate hydrolysis in PBS occurs. 3 is readily reduced with ascorbic acid and forms adducts with bovine serum albumin (BSA). In vitro anticancer activity of the gold(III) complexes against human cervix adenocarcinoma HeLa, human myelogenous leukemia K562, human melanoma Fem-x tumor cell lines, as well as against non-cancerous human embryonic lung fibroblast cell line MRC-5 was determined using MTT assay. Complex 4 showed highest activity and selectivity (IC50(Fem-x) = 1.3 ± 0.2; IC50(MRC-5)/IC50(Fem-x) = 72.5 ± 12.4), 4 times more active and 28 times more selective than cisplatin. Complexes induced apoptotic mode of death in a time-dependent manner in HeLa cells.
Publikation

Pantelić, N.; Zmejkovski, B. B.; Stanojković, T. P.; Jeftić, V. V.; Radić, G. P.; Trifunović, S. R.; Kaluđerović, G. N.; Sabo, T. J.; Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N’-di-2-propanoate dihydrochloride esters J. Serb. Chem. Soc. 79, 649-658, (2014) DOI: 10.2298/JSC130512022P

A novel (S,S)-R2eddip ester, O,O′-diisopentyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, 1H- and 13C-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R2eddip esters, dialkyl (S,S)-ethylenediamine-N,N′-di-2-propanoate dihydrochlorides, obtained before (alkyl = n-Bu or n-Pe, 2 and 3, respectively), was determined against cervix adenocarcinoma (HeLa), human melanoma (Fem-x), human chronic myelogenous leukemia (K562) cells, and a non-cancerous cell line human embryonic lung fibroblast (MRC-5), using the microculture tetrazolium test MTT assay. Esters 1–3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activity was expressed by 1, with IC50(Fem-x) value of 1.51±0.09 μM.
Publikation

Zmejkovski, B. B.; Savić, A.; Poljarević, J.; Pantelić, N.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.; Kaluđerović, G. N.; Sabo, T. J.; Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R2edda-type esters Polyhedron 80, 106-111, (2014) DOI: 10.1016/j.poly.2014.02.026

Six palladium(II) complexes with (S,S)-R2edda-type esters ((S,S)-R2edda-type: (S,S)-eddch = (S,S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1–3; (S,S)-pddch = (S,S)-propylenediamine-N,N′-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N′-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1–4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N′-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N′ configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential against HeLa (IC50: 28.5 ± 3.9, 29.5 ± 1.3 and 34.3 ± 3.2, respectively).

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