Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands
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2012
Authors
Vujic, Jelena M.Kaluđerović, Goran N.

Zmejkovski, Bojana

Milovanovic, Marija
Volarevic, Vladislav
Arsenijevic, Nebojsa

Stanojković, Tatjana

Trifunovic, Srecko R.
Article (Published version)

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Synthesis of four new platinum(IV) complexes 1-4, with bidentate N,N'-ligand precursors O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 were reported. The composition of the novel platinum complexes was determined by elemental analysis and characterizations were performed by infrared, H-1 and C-13 NMR spectroscopy. DFT calculations indicate formation one (R,R) from three possible diastereoisomers (S,S; R,S). Complexes 1-4 displayed potent anticancer activity. IC50 values range from 0.74 to 70 mu M, against tested cell lines, except for CLL cells. The antitumoral activity of 2-4 was found to be considerably stronger to Jurkat and K562. Cell cycle analysis of cell lines showed G1 arrest in the presence of analyzed complexes.
Keywords:
Platinum(IV) complexes / EDDA-type ligands / Antitumoral activity / Cell cycle / ApoptosisSource:
Inorganica Chimica Acta, 2012, 390, 123-128Publisher:
- Elsevier Science Sa, Lausanne
Funding / projects:
- Molecular determinants of innate immunity in autoimmunity and tumorogenesis (RS-175069)
- Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-172016)
- 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)
- EC under FP7 Research Potential Program (CPCTAS)
DOI: 10.1016/j.ica.2012.03.048
ISSN: 0020-1693
WoS: 000305811000018
Scopus: 2-s2.0-84861157759
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Institution/Community
IHTMTY - JOUR AU - Vujic, Jelena M. AU - Kaluđerović, Goran N. AU - Zmejkovski, Bojana AU - Milovanovic, Marija AU - Volarevic, Vladislav AU - Arsenijevic, Nebojsa AU - Stanojković, Tatjana AU - Trifunovic, Srecko R. PY - 2012 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/969 AB - Synthesis of four new platinum(IV) complexes 1-4, with bidentate N,N'-ligand precursors O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 were reported. The composition of the novel platinum complexes was determined by elemental analysis and characterizations were performed by infrared, H-1 and C-13 NMR spectroscopy. DFT calculations indicate formation one (R,R) from three possible diastereoisomers (S,S; R,S). Complexes 1-4 displayed potent anticancer activity. IC50 values range from 0.74 to 70 mu M, against tested cell lines, except for CLL cells. The antitumoral activity of 2-4 was found to be considerably stronger to Jurkat and K562. Cell cycle analysis of cell lines showed G1 arrest in the presence of analyzed complexes. PB - Elsevier Science Sa, Lausanne T2 - Inorganica Chimica Acta T1 - Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands VL - 390 SP - 123 EP - 128 DO - 10.1016/j.ica.2012.03.048 ER -
@article{ author = "Vujic, Jelena M. and Kaluđerović, Goran N. and Zmejkovski, Bojana and Milovanovic, Marija and Volarevic, Vladislav and Arsenijevic, Nebojsa and Stanojković, Tatjana and Trifunovic, Srecko R.", year = "2012", abstract = "Synthesis of four new platinum(IV) complexes 1-4, with bidentate N,N'-ligand precursors O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 were reported. The composition of the novel platinum complexes was determined by elemental analysis and characterizations were performed by infrared, H-1 and C-13 NMR spectroscopy. DFT calculations indicate formation one (R,R) from three possible diastereoisomers (S,S; R,S). Complexes 1-4 displayed potent anticancer activity. IC50 values range from 0.74 to 70 mu M, against tested cell lines, except for CLL cells. The antitumoral activity of 2-4 was found to be considerably stronger to Jurkat and K562. Cell cycle analysis of cell lines showed G1 arrest in the presence of analyzed complexes.", publisher = "Elsevier Science Sa, Lausanne", journal = "Inorganica Chimica Acta", title = "Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands", volume = "390", pages = "123-128", doi = "10.1016/j.ica.2012.03.048" }
Vujic, J. M., Kaluđerović, G. N., Zmejkovski, B., Milovanovic, M., Volarevic, V., Arsenijevic, N., Stanojković, T.,& Trifunovic, S. R.. (2012). Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands. in Inorganica Chimica Acta Elsevier Science Sa, Lausanne., 390, 123-128. https://doi.org/10.1016/j.ica.2012.03.048
Vujic JM, Kaluđerović GN, Zmejkovski B, Milovanovic M, Volarevic V, Arsenijevic N, Stanojković T, Trifunovic SR. Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands. in Inorganica Chimica Acta. 2012;390:123-128. doi:10.1016/j.ica.2012.03.048 .
Vujic, Jelena M., Kaluđerović, Goran N., Zmejkovski, Bojana, Milovanovic, Marija, Volarevic, Vladislav, Arsenijevic, Nebojsa, Stanojković, Tatjana, Trifunovic, Srecko R., "Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands" in Inorganica Chimica Acta, 390 (2012):123-128, https://doi.org/10.1016/j.ica.2012.03.048 . .