TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Zmejkovski, Bojana
AU  - Kolundzija, Branka
AU  - Crnogorac, Marija Dordic
AU  - Vujic, Jelena M.
AU  - Dojčinović, Biljana
AU  - Trifunovic, Srecko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2248
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = 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 mu M). 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.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - 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
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 

@article{
author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Kolundzija, Branka and Crnogorac, Marija Dordic and Vujic, Jelena M. and Dojčinović, Biljana and Trifunovic, Srecko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = 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 mu M). 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.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "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",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}

Pantelic, N., Zmejkovski, B., Kolundzija, B., Crnogorac, M. D., Vujic, J. M., Dojčinović, B., Trifunovic, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). 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. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001

Pantelic N, Zmejkovski B, Kolundzija B, Crnogorac MD, Vujic JM, Dojčinović B, Trifunovic SR, Stanojković T, Sabo T, Kaluđerović GN. 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. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .

Pantelic, Nebojsa, Zmejkovski, Bojana, Kolundzija, Branka, Crnogorac, Marija Dordic, Vujic, Jelena M., Dojčinović, Biljana, Trifunovic, Srecko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran 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" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .

TY  - JOUR
AU  - Zmejkovski, Bojana
AU  - Pantelic, Nebojsa
AU  - Filipovic, Lana
AU  - Arandelovic, Sandra
AU  - Radulovic, Sinisa
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2132
AB  - Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 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 C-13 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 mu M), 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.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Anti-Cancer Agents in Medicinal Chemistry
T1  - In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid
VL  - 17
IS  - 8
SP  - 1136
EP  - 1143
DO  - 10.2174/1871520616666161207155634
ER  - 

@article{
author = "Zmejkovski, Bojana and Pantelic, Nebojsa and Filipovic, Lana and Arandelovic, Sandra and Radulovic, Sinisa and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 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 C-13 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 mu M), 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.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Anti-Cancer Agents in Medicinal Chemistry",
title = "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid",
volume = "17",
number = "8",
pages = "1136-1143",
doi = "10.2174/1871520616666161207155634"
}

Zmejkovski, B., Pantelic, N., Filipovic, L., Arandelovic, S., Radulovic, S., Sabo, T.,& Kaluđerović, G. N.. (2017). In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry
Bentham Science Publ Ltd, Sharjah., 17(8), 1136-1143.
https://doi.org/10.2174/1871520616666161207155634

Zmejkovski B, Pantelic N, Filipovic L, Arandelovic S, Radulovic S, Sabo T, Kaluđerović GN. In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry. 2017;17(8):1136-1143.
doi:10.2174/1871520616666161207155634 .

Zmejkovski, Bojana, Pantelic, Nebojsa, Filipovic, Lana, Arandelovic, Sandra, Radulovic, Sinisa, Sabo, Tibor, Kaluđerović, Goran N., "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid" in Anti-Cancer Agents in Medicinal Chemistry, 17, no. 8 (2017):1136-1143,
https://doi.org/10.2174/1871520616666161207155634 . .

TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Zmejkovski, Bojana
AU  - Markovic, Dragana D
AU  - Vujic, Jelena M
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1938
AB  - A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), 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)-H(2)Et(2)eddl]Cl-2 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)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.
PB  - MDPI
T2  - Metals
T1  - 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
VL  - 6
IS  - 9
DO  - 10.3390/met6090226
ER  - 

@article{
author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Markovic, Dragana D and Vujic, Jelena M and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2016",
abstract = "A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), 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)-H(2)Et(2)eddl]Cl-2 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)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.",
publisher = "MDPI",
journal = "Metals",
title = "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",
volume = "6",
number = "9",
doi = "10.3390/met6090226"
}

Pantelic, N., Zmejkovski, B., Markovic, D. D., Vujic, J. M., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2016). 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. in Metals
MDPI., 6(9).
https://doi.org/10.3390/met6090226

Pantelic N, Zmejkovski B, Markovic DD, Vujic JM, Stanojković T, Sabo T, Kaluđerović GN. 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. in Metals. 2016;6(9).
doi:10.3390/met6090226 .

Pantelic, Nebojsa, Zmejkovski, Bojana, Markovic, Dragana D, Vujic, Jelena M, Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran 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" in Metals, 6, no. 9 (2016),
https://doi.org/10.3390/met6090226 . .

TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Stanković, Dalibor
AU  - Zmejkovski, Bojana
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1963
AB  - Oxidation-reduction properties of eleven gold(III) complexes with (S,S)-R(2)edda-type ligands was studied by cyclic and differential pulse voltammetry in DMSO. Series I: [AuCl2{(S,S)-R(2)eddip}]PF6, (S,S)-eddip = (S,S)-ethylenediamine-N,N'-di-2-propanoate, R = n-butyl, n-pentyl, isobutyl, isoamyl, cyclopentyl, 1-5; II: [AuCl2{(S,S)-R(2)eddch}]PF6, (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = methyl, ethyl, n-propyl, n-butyl, isobutyl, isoamyl, 6-11. Voltammograms in DMSO showed two successive irreversible reduction steps, where Au-I species were the final reduction product. Reduction potential values are in range from 116 to 156 mV (Ep(1)) and -520 to -572 mV (Ep(2)) for Series I and from 148 to 228 mV (Ep(1)) and -569 to -638 mV (Ep(2)) for Series II. In general, slightly easier reduction of complexes belonging to Series I (higher cytotoxicity) could be due to less steric hindrance around the gold center. Reduction potentials and anticancer activity are not in correlation.
PB  - Esg, Belgrade
T2  - International Journal of Electrochemical Science
T1  - Electrochemical properties of some gold(III) complexes with (S,S)-R(2)edda-type ligands
VL  - 11
IS  - 2
SP  - 1162
EP  - 1171
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2060
ER  - 

@article{
author = "Pantelic, Nebojsa and Stanković, Dalibor and Zmejkovski, Bojana and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2016",
abstract = "Oxidation-reduction properties of eleven gold(III) complexes with (S,S)-R(2)edda-type ligands was studied by cyclic and differential pulse voltammetry in DMSO. Series I: [AuCl2{(S,S)-R(2)eddip}]PF6, (S,S)-eddip = (S,S)-ethylenediamine-N,N'-di-2-propanoate, R = n-butyl, n-pentyl, isobutyl, isoamyl, cyclopentyl, 1-5; II: [AuCl2{(S,S)-R(2)eddch}]PF6, (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = methyl, ethyl, n-propyl, n-butyl, isobutyl, isoamyl, 6-11. Voltammograms in DMSO showed two successive irreversible reduction steps, where Au-I species were the final reduction product. Reduction potential values are in range from 116 to 156 mV (Ep(1)) and -520 to -572 mV (Ep(2)) for Series I and from 148 to 228 mV (Ep(1)) and -569 to -638 mV (Ep(2)) for Series II. In general, slightly easier reduction of complexes belonging to Series I (higher cytotoxicity) could be due to less steric hindrance around the gold center. Reduction potentials and anticancer activity are not in correlation.",
publisher = "Esg, Belgrade",
journal = "International Journal of Electrochemical Science",
title = "Electrochemical properties of some gold(III) complexes with (S,S)-R(2)edda-type ligands",
volume = "11",
number = "2",
pages = "1162-1171",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2060"
}

Pantelic, N., Stanković, D., Zmejkovski, B., Kaluđerović, G. N.,& Sabo, T.. (2016). Electrochemical properties of some gold(III) complexes with (S,S)-R(2)edda-type ligands. in International Journal of Electrochemical Science
Esg, Belgrade., 11(2), 1162-1171.
https://hdl.handle.net/21.15107/rcub_cherry_2060

Pantelic N, Stanković D, Zmejkovski B, Kaluđerović GN, Sabo T. Electrochemical properties of some gold(III) complexes with (S,S)-R(2)edda-type ligands. in International Journal of Electrochemical Science. 2016;11(2):1162-1171.
https://hdl.handle.net/21.15107/rcub_cherry_2060 .

Pantelic, Nebojsa, Stanković, Dalibor, Zmejkovski, Bojana, Kaluđerović, Goran N., Sabo, Tibor, "Electrochemical properties of some gold(III) complexes with (S,S)-R(2)edda-type ligands" in International Journal of Electrochemical Science, 11, no. 2 (2016):1162-1171,
https://hdl.handle.net/21.15107/rcub_cherry_2060 .