Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate
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2013
Authors
Pantelić, Nebojša
Zmejkovski, Bojana B.
Trifunović-Macedoljan, Jelena
Savić, Aleksandar

Stanković, Dalibor

Damjanović, Ana
Juranić, Zorica
Kaludjerović, Goran N.

Sabo, Tibor J.

Article (Published version)

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Show full item recordAbstract
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 / CytotoxicitySource:
Journal of Inorganic Biochemistry, 2013, 128, 146-153Publisher:
- 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
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Institution/Community
Poljoprivredni fakultetTY - JOUR AU - Pantelić, Nebojša AU - Zmejkovski, Bojana B. AU - Trifunović-Macedoljan, Jelena AU - Savić, Aleksandar AU - Stanković, Dalibor AU - Damjanović, Ana AU - Juranić, Zorica AU - Kaludjerović, Goran N. AU - Sabo, Tibor J. PY - 2013 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/3140 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 EP - 153 SP - 146 VL - 128 DO - 10.1016/j.jinorgbio.2013.08.002 ER -
@article{ author = "Pantelić, Nebojša and Zmejkovski, Bojana B. and Trifunović-Macedoljan, Jelena and Savić, Aleksandar and Stanković, Dalibor and Damjanović, Ana and Juranić, Zorica and Kaludjerović, Goran N. and Sabo, Tibor J.", 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", pages = "153-146", volume = "128", doi = "10.1016/j.jinorgbio.2013.08.002" }
Pantelić, N., Zmejkovski, B. B., Trifunović-Macedoljan, J., Savić, A., Stanković, D., Damjanović, A., Juranić, Z., Kaludjerović, G. N.,& Sabo, T. J.. (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 N, Zmejkovski BB, Trifunović-Macedoljan J, Savić A, Stanković D, Damjanović A, Juranić Z, Kaludjerović GN, Sabo TJ. 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, Zmejkovski, Bojana B., Trifunović-Macedoljan, Jelena, Savić, Aleksandar, Stanković, Dalibor, Damjanović, Ana, Juranić, Zorica, Kaludjerović, Goran N., Sabo, Tibor J., "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 . .