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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

Authorized Users Only
2017
Authors
Pantelić, Nebojša Đ.
Zmejkovski, Bojana B.
Kolundžija, Branka
Crnogorac, Marija Đorđić
Vujić, Jelena M.
Dojčinović, Biljana P.
Trifunović, Srećko R.
Stanojković, Tatjana
Sabo, Tibor
Kaluđerović, Goran N.
Article (Published version)
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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 cell...s 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.

Keywords:
Gold(III) complexes / R(2)edda-type ligands / Metal uptake / Apoptosis / Biological reactivity
Source:
Journal of Inorganic Biochemistry, 2017, 172, 55-66
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)
  • Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-172016)
  • Biological response modifiers in physiological and pathological conditions (RS-175011)
Note:
  • Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3070
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3071

DOI: 10.1016/j.jinorgbio.2017.04.001

ISSN: 0162-0134

PubMed: 28433833

WoS: 000404000300007

Scopus: 2-s2.0-85017584556
[ Google Scholar ]
12
8
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2478
Collections
  • Publikacije / Publications
Institution/Community
Hemijski fakultet / Faculty of Chemistry
TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana B.
AU  - Kolundžija, Branka
AU  - Crnogorac, Marija Đorđić
AU  - Vujić, Jelena M.
AU  - Dojčinović, Biljana P.
AU  - Trifunović, Srećko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2478
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 = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana B. and Kolundžija, Branka and Crnogorac, Marija Đorđić and Vujić, Jelena M. and Dojčinović, Biljana P. and Trifunović, Srećko 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"
}
Pantelić, N. Đ., Zmejkovski, B. B., Kolundžija, B., Crnogorac, M. Đ., Vujić, J. M., Dojčinović, B. P., Trifunović, 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
Pantelić NĐ, Zmejkovski BB, Kolundžija B, Crnogorac MĐ, Vujić JM, Dojčinović BP, Trifunović 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 .
Pantelić, Nebojša Đ., Zmejkovski, Bojana B., Kolundžija, Branka, Crnogorac, Marija Đorđić, Vujić, Jelena M., Dojčinović, Biljana P., Trifunović, Srećko 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 . .

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