Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters
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2014
Authors
Zmejkovski, Bojana B.Savić, Aleksandar

Poljarević, Jelena

Pantelić, Nebojša

Arandelović, Sandra
Radulović, Siniša
Grgurić-Šipka, Sanja

Kaludjerović, Goran N.

Sabo, Tibor J.

Article (Published version)

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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 activitySource:
Polyhedron, 2014, 80, 106-111Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- 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)
- 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)
DOI: 10.1016/j.poly.2014.02.026
ISSN: 0277-5387
WoS: 000341348300014
Scopus: 2-s2.0-84905493340
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Poljoprivredni fakultetTY - JOUR AU - Zmejkovski, Bojana B. AU - Savić, Aleksandar AU - Poljarević, Jelena AU - Pantelić, Nebojša AU - Arandelović, Sandra AU - Radulović, Siniša AU - Grgurić-Šipka, Sanja AU - Kaludjerović, Goran N. AU - Sabo, Tibor J. PY - 2014 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/3400 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 - Pergamon-Elsevier Science Ltd, Oxford T2 - Polyhedron T1 - Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters EP - 111 SP - 106 VL - 80 DO - 10.1016/j.poly.2014.02.026 ER -
@article{ author = "Zmejkovski, Bojana B. and Savić, Aleksandar and Poljarević, Jelena and Pantelić, Nebojša and Arandelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja and Kaludjerović, Goran N. and Sabo, Tibor J.", 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 = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Polyhedron", title = "Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters", pages = "111-106", volume = "80", doi = "10.1016/j.poly.2014.02.026" }
Zmejkovski, B. B., Savić, A., Poljarević, J., Pantelić, N., Arandelović, S., Radulović, S., Grgurić-Šipka, S., Kaludjerović, G. N.,& Sabo, T. J.. (2014). Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters. in Polyhedron Pergamon-Elsevier Science Ltd, Oxford., 80, 106-111. https://doi.org/10.1016/j.poly.2014.02.026
Zmejkovski BB, Savić A, Poljarević J, Pantelić N, Arandelović S, Radulović S, Grgurić-Šipka S, Kaludjerović GN, Sabo TJ. 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 B., Savić, Aleksandar, Poljarević, Jelena, Pantelić, Nebojša, Arandelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, Kaludjerović, Goran N., Sabo, Tibor J., "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 . .