Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]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 MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 1.3 +/- 0.2; IC50(MRC-5)/IC50(Fem-x) = 72.5 +/- 12.4), 4 times more active and 28 times more sel...ective than cisplatin. Complexes induced apoptotic mode of death in a time-dependent manner in HeLa cells.
TY - JOUR
AU - Pantelić, Nebojša
AU - Stanojković, Tatjana P.
AU - Zmejkovski, Bojana B.
AU - Sabo, Tibor J.
AU - Kaludjerović, Goran N.
PY - 2015
UR - http://aspace.agrif.bg.ac.rs/handle/123456789/3779
AB - Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]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 MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 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.
PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2 - European Journal of Medicinal Chemistry
T1 - In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid
EP - 774
SP - 766
VL - 90
DO - 10.1016/j.ejmech.2014.12.019
ER -
@article{
author = "Pantelić, Nebojša and Stanojković, Tatjana P. and Zmejkovski, Bojana B. and Sabo, Tibor J. and Kaludjerović, Goran N.",
year = "2015",
abstract = "Five novel gold(III) complexes of general formulas [AuCl2{(S,S)-R(2)eddip}]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 MRC5 was determined using MIT assay. Complex 4 showed highest activity and selectivity (IC50(Femx) = 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.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid",
pages = "774-766",
volume = "90",
doi = "10.1016/j.ejmech.2014.12.019"
}
Pantelić, N., Stanojković, T. P., Zmejkovski, B. B., Sabo, T. J.,& Kaludjerović, G. N.. (2015). In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 90, 766-774.
https://doi.org/10.1016/j.ejmech.2014.12.019
Pantelić N, Stanojković TP, Zmejkovski BB, Sabo TJ, Kaludjerović GN. In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid. in European Journal of Medicinal Chemistry. 2015;90:766-774.
doi:10.1016/j.ejmech.2014.12.019 .
Pantelić, Nebojša, Stanojković, Tatjana P., Zmejkovski, Bojana B., Sabo, Tibor J., Kaludjerović, Goran N., "In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N '-di-2-propanoic acid" in European Journal of Medicinal Chemistry, 90 (2015):766-774,
https://doi.org/10.1016/j.ejmech.2014.12.019 . .
