Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N '-diacetate
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2013
Authors
Pantelić, Nebojša Đ.Zmejkovski, Bojana B.
Trifunović-Macedoljan, Jelena
Savić, Aleksandar
Stanković, Dalibor
Damjanović, Ana
Juranić, Zorica D.
Kaluđerović, Goran N.
Sabo, Tibor
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)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3497
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
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Pantelić, Nebojša Đ. AU - Zmejkovski, Bojana B. AU - Trifunović-Macedoljan, Jelena AU - Savić, Aleksandar AU - Stanković, Dalibor AU - Damjanović, Ana AU - Juranić, Zorica D. AU - Kaluđerović, Goran N. AU - Sabo, Tibor PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1422 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 B. and Trifunović-Macedoljan, Jelena and Savić, Aleksandar and Stanković, Dalibor and Damjanović, Ana and Juranić, Zorica D. 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. B., Trifunović-Macedoljan, J., Savić, A., Stanković, D., Damjanović, A., Juranić, Z. D., 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 BB, Trifunović-Macedoljan J, Savić A, Stanković D, Damjanović A, Juranić ZD, 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 B., Trifunović-Macedoljan, Jelena, Savić, Aleksandar, Stanković, Dalibor, Damjanović, Ana, Juranić, Zorica D., 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 . .