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  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana
AU  - Stanojković, Tatjana
AU  - Jevtic, Verica V.
AU  - Radic, Gordana P.
AU  - Trifunovic, Srecko R.
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1574
AB  - A novel (S,S)-R(2)eddip ester, O,O'-diisopentyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, H-1- and C-13-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R(2)eddip 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 mu M.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters
VL  - 79
IS  - 6
SP  - 649
EP  - 658
DO  - 10.2298/JSC130512022P
ER  - 

@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana and Stanojković, Tatjana and Jevtic, Verica V. and Radic, Gordana P. and Trifunovic, Srecko R. and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2014",
abstract = "A novel (S,S)-R(2)eddip ester, O,O'-diisopentyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate dihydrochloride (1) was synthesized and characterized by IR, H-1- and C-13-NMR spectroscopy, mass spectroscopy and elemental analysis. In vitro antitumor action of 1, and two more R(2)eddip 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 mu M.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters",
volume = "79",
number = "6",
pages = "649-658",
doi = "10.2298/JSC130512022P"
}

Pantelić, N. Đ., Zmejkovski, B., Stanojković, T., Jevtic, V. V., Radic, G. P., Trifunovic, S. R., Kaluđerović, G. N.,& Sabo, T.. (2014). Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 79(6), 649-658.
https://doi.org/10.2298/JSC130512022P

Pantelić NĐ, Zmejkovski B, Stanojković T, Jevtic VV, Radic GP, Trifunovic SR, Kaluđerović GN, Sabo T. Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters. in Journal of the Serbian Chemical Society. 2014;79(6):649-658.
doi:10.2298/JSC130512022P .

Pantelić, Nebojša Đ., Zmejkovski, Bojana, Stanojković, Tatjana, Jevtic, Verica V., Radic, Gordana P., Trifunovic, Srecko R., Kaluđerović, Goran N., Sabo, Tibor, "Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N '-di-2-propanoate dihydrochloride esters" in Journal of the Serbian Chemical Society, 79, no. 6 (2014):649-658,
https://doi.org/10.2298/JSC130512022P . .

TY  - JOUR
AU  - Vujic, Jelena M.
AU  - Cvijovic, Milica
AU  - Kaluđerović, Goran N.
AU  - Milovanovic, Marija
AU  - Zmejkovski, Bojana
AU  - Volarevic, Vladislav
AU  - Arsenijevic, Nebojsa
AU  - Sabo, Tibor
AU  - Trifunovic, Srecko R.
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/710
AB  - Four novel bidentate N,N'-ligand precursors, including O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), L1 center dot 2HCl-L4 center dot 2HCl, of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)-pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 and the corresponding palladium(II) complexes 1-4, were prepared and characterized by IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. In vitro cytotoxicity of all compounds was determined against chronic lymphocytic leukemia cells (CLL). The compounds were found to exhibit higher antitumoral activity than cisplatin. The most active compound 2, [PdCl2{(S,S)-nPr(2)eddl}], was found to be 13.6 times more active than cisplatin on CLL cells.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral acti
VL  - 45
IS  - 9
SP  - 3601
EP  - 3606
DO  - 10.1016/j.ejmech.2010.05.005
ER  - 

@article{
author = "Vujic, Jelena M. and Cvijovic, Milica and Kaluđerović, Goran N. and Milovanovic, Marija and Zmejkovski, Bojana and Volarevic, Vladislav and Arsenijevic, Nebojsa and Sabo, Tibor and Trifunovic, Srecko R.",
year = "2010",
abstract = "Four novel bidentate N,N'-ligand precursors, including O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), L1 center dot 2HCl-L4 center dot 2HCl, of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)-pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 and the corresponding palladium(II) complexes 1-4, were prepared and characterized by IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. In vitro cytotoxicity of all compounds was determined against chronic lymphocytic leukemia cells (CLL). The compounds were found to exhibit higher antitumoral activity than cisplatin. The most active compound 2, [PdCl2{(S,S)-nPr(2)eddl}], was found to be 13.6 times more active than cisplatin on CLL cells.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral acti",
volume = "45",
number = "9",
pages = "3601-3606",
doi = "10.1016/j.ejmech.2010.05.005"
}

Vujic, J. M., Cvijovic, M., Kaluđerović, G. N., Milovanovic, M., Zmejkovski, B., Volarevic, V., Arsenijevic, N., Sabo, T.,& Trifunovic, S. R.. (2010). Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral acti. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 45(9), 3601-3606.
https://doi.org/10.1016/j.ejmech.2010.05.005

Vujic JM, Cvijovic M, Kaluđerović GN, Milovanovic M, Zmejkovski B, Volarevic V, Arsenijevic N, Sabo T, Trifunovic SR. Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral acti. in European Journal of Medicinal Chemistry. 2010;45(9):3601-3606.
doi:10.1016/j.ejmech.2010.05.005 .

Vujic, Jelena M., Cvijovic, Milica, Kaluđerović, Goran N., Milovanovic, Marija, Zmejkovski, Bojana, Volarevic, Vladislav, Arsenijevic, Nebojsa, Sabo, Tibor, Trifunovic, Srecko R., "Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral acti" in European Journal of Medicinal Chemistry, 45, no. 9 (2010):3601-3606,
https://doi.org/10.1016/j.ejmech.2010.05.005 . .