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Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters

Authorized Users Only
2014
Authors
Zmejkovski, Bojana
Savic, Aleksandar
Poljarevic, Jelena
Pantelić, Nebojša Đ.
Arandelovic, Sandra
Radulovic, Sinisa
Grgurić-Šipka, Sanja
Kaluđerović, Goran N.
Sabo, Tibor
Article (Published version)
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Abstract
Six palladium(II) complexes with (S,S)-R(2)edda-type esters ((S,S)-R2edda-type; (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1-3; (S,S)-pddch = (S,S)-propylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N'-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1-4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N'-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N' configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential... against HeLa (IC50: 28.5 +/- 3.9, 29.5 +/- 1.3 and 34.3 +/- 3.2, respectively).

Keywords:
Palladium(II) complexes / R(2)edda-type ligands / DFT calculations / Diastereoisomers / cytotoxic activity
Source:
Polyhedron, 2014, 80, 106-111
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors (RS-41026)
  • Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)

DOI: 10.1016/j.poly.2014.02.026

ISSN: 0277-5387

WoS: 000341348300014

Scopus: 2-s2.0-84905493340
[ Google Scholar ]
15
11
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1442
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Zmejkovski, Bojana
AU  - Savic, Aleksandar
AU  - Poljarevic, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Arandelovic, Sandra
AU  - Radulovic, Sinisa
AU  - Grgurić-Šipka, Sanja
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1442
AB  - Six palladium(II) complexes with (S,S)-R(2)edda-type esters ((S,S)-R2edda-type; (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1-3; (S,S)-pddch = (S,S)-propylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N'-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1-4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N'-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N' configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential against HeLa (IC50: 28.5 +/- 3.9, 29.5 +/- 1.3 and 34.3 +/- 3.2, respectively).
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters
VL  - 80
SP  - 106
EP  - 111
DO  - 10.1016/j.poly.2014.02.026
ER  - 
@article{
author = "Zmejkovski, Bojana and Savic, Aleksandar and Poljarevic, Jelena and Pantelić, Nebojša Đ. and Arandelovic, Sandra and Radulovic, Sinisa and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2014",
abstract = "Six palladium(II) complexes with (S,S)-R(2)edda-type esters ((S,S)-R2edda-type; (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1-3; (S,S)-pddch = (S,S)-propylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N'-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1-4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N'-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N' configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential against HeLa (IC50: 28.5 +/- 3.9, 29.5 +/- 1.3 and 34.3 +/- 3.2, respectively).",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters",
volume = "80",
pages = "106-111",
doi = "10.1016/j.poly.2014.02.026"
}
Zmejkovski, B., Savic, A., Poljarevic, J., Pantelić, N. Đ., Arandelovic, S., Radulovic, S., Grgurić-Šipka, S., Kaluđerović, G. N.,& Sabo, T.. (2014). Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 80, 106-111.
https://doi.org/10.1016/j.poly.2014.02.026
Zmejkovski B, Savic A, Poljarevic J, Pantelić NĐ, Arandelovic S, Radulovic S, Grgurić-Šipka S, Kaluđerović GN, Sabo T. Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters. in Polyhedron. 2014;80:106-111.
doi:10.1016/j.poly.2014.02.026 .
Zmejkovski, Bojana, Savic, Aleksandar, Poljarevic, Jelena, Pantelić, Nebojša Đ., Arandelovic, Sandra, Radulovic, Sinisa, Grgurić-Šipka, Sanja, Kaluđerović, Goran N., Sabo, Tibor, "Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters" in Polyhedron, 80 (2014):106-111,
https://doi.org/10.1016/j.poly.2014.02.026 . .

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