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Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate

Authorized Users Only
2013
Authors
Pantelić, Nebojša Đ.
Zmejkovski, Bojana
Trifunovic-Macedoljan, Jelena
Savic, Aleksandar
Stanković, Dalibor
Damjanovic, Ana
Juranić, Zorica
Kaluđerović, Goran N.
Sabo, Tibor
Article (Published version)
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Abstract
Six novel gold(III) complexes containing O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate ([AuCl2{(S,S)-R(2)eddch}]PF6, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am; 1-6, respectively) were synthesized and characterized by elemental analysis, UV/Visible, IR and NMR spectroscopy, mass spectrometry and differential pulse voltammetry. Density functional theory (DFT) calculations confirmed that diastereoisomer with the N,N' atoms configured (S,S) was the most stable. In vitro antiproliferative activity was determined against human cervix adenocarcinoma HeLa and human myelogenous leukemia K562 tumor cell lines, as well as against rested and stimulated normal immunocompetent human peripheral blood mononuclear cells (PBMC) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Complex 6 expressed the highest activity against K562 cells (IC50 = 3.8 +/- 0.5 mu M). Apoptosis, seen as condensation of HeLa cell nuclei was the mode of cell death induced by comple...xes 2-6. Complexes 3-6 induced death of K562 cells inhibiting cell entry in mitosis.

Keywords:
Gold(III) complexes / R(2)edda-type ligands / DFT / Apoptosis / Cell cycle / cytotoxicity
Source:
Journal of Inorganic Biochemistry, 2013, 128, 146-153
Publisher:
  • Elsevier Science Inc, New York
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Biological response modifiers in physiological and pathological conditions (RS-175011)

DOI: 10.1016/j.jinorgbio.2013.08.002

ISSN: 0162-0134

PubMed: 23988849

WoS: 000326060800017

Scopus: 2-s2.0-84882759461
[ Google Scholar ]
21
17
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1211
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana
AU  - Trifunovic-Macedoljan, Jelena
AU  - Savic, Aleksandar
AU  - Stanković, Dalibor
AU  - Damjanovic, Ana
AU  - Juranić, Zorica
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1211
AB  - Six novel gold(III) complexes containing O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate ([AuCl2{(S,S)-R(2)eddch}]PF6, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am; 1-6, respectively) were synthesized and characterized by elemental analysis, UV/Visible, IR and NMR spectroscopy, mass spectrometry and differential pulse voltammetry. Density functional theory (DFT) calculations confirmed that diastereoisomer with the N,N' atoms configured (S,S) was the most stable. In vitro antiproliferative activity was determined against human cervix adenocarcinoma HeLa and human myelogenous leukemia K562 tumor cell lines, as well as against rested and stimulated normal immunocompetent human peripheral blood mononuclear cells (PBMC) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Complex 6 expressed the highest activity against K562 cells (IC50 = 3.8 +/- 0.5 mu M). Apoptosis, seen as condensation of HeLa cell nuclei was the mode of cell death induced by complexes 2-6. Complexes 3-6 induced death of K562 cells inhibiting cell entry in mitosis.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate
VL  - 128
SP  - 146
EP  - 153
DO  - 10.1016/j.jinorgbio.2013.08.002
ER  - 
@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana and Trifunovic-Macedoljan, Jelena and Savic, Aleksandar and Stanković, Dalibor and Damjanovic, Ana and Juranić, Zorica and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2013",
abstract = "Six novel gold(III) complexes containing O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate ([AuCl2{(S,S)-R(2)eddch}]PF6, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am; 1-6, respectively) were synthesized and characterized by elemental analysis, UV/Visible, IR and NMR spectroscopy, mass spectrometry and differential pulse voltammetry. Density functional theory (DFT) calculations confirmed that diastereoisomer with the N,N' atoms configured (S,S) was the most stable. In vitro antiproliferative activity was determined against human cervix adenocarcinoma HeLa and human myelogenous leukemia K562 tumor cell lines, as well as against rested and stimulated normal immunocompetent human peripheral blood mononuclear cells (PBMC) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Complex 6 expressed the highest activity against K562 cells (IC50 = 3.8 +/- 0.5 mu M). Apoptosis, seen as condensation of HeLa cell nuclei was the mode of cell death induced by complexes 2-6. Complexes 3-6 induced death of K562 cells inhibiting cell entry in mitosis.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate",
volume = "128",
pages = "146-153",
doi = "10.1016/j.jinorgbio.2013.08.002"
}
Pantelić, N. Đ., Zmejkovski, B., Trifunovic-Macedoljan, J., Savic, A., Stanković, D., Damjanovic, A., Juranić, Z., Kaluđerović, G. N.,& Sabo, T.. (2013). Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 128, 146-153.
https://doi.org/10.1016/j.jinorgbio.2013.08.002
Pantelić NĐ, Zmejkovski B, Trifunovic-Macedoljan J, Savic A, Stanković D, Damjanovic A, Juranić Z, Kaluđerović GN, Sabo T. Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate. in Journal of Inorganic Biochemistry. 2013;128:146-153.
doi:10.1016/j.jinorgbio.2013.08.002 .
Pantelić, Nebojša Đ., Zmejkovski, Bojana, Trifunovic-Macedoljan, Jelena, Savic, Aleksandar, Stanković, Dalibor, Damjanovic, Ana, Juranić, Zorica, Kaluđerović, Goran N., Sabo, Tibor, "Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate" in Journal of Inorganic Biochemistry, 128 (2013):146-153,
https://doi.org/10.1016/j.jinorgbio.2013.08.002 . .

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