Synthesis, characterization and antitumor activity of polymeric copper(II) complexes with thiosemicarbazones of 3-methyl-5-oxo-1-phenyl-3-pyrazolin-4-carboxaldehyde and 5-oxo-3-phenyl-3-pyrazolin-4-carboxaldehyde

被引:38
作者
Leovac, Vukadin M. [1 ]
Bogdanovic, Goran A. [2 ]
Jovanovic, Ljiljana S. [1 ]
Joksovic, Ljubinka [3 ]
Markovic, Violeta [3 ]
Joksovic, Milan D. [3 ]
Dencic, Sonja Misirlic [4 ]
Isakovic, Andelka [4 ]
Markovic, Ivanka [4 ]
Heinemann, Frank W. [5 ]
Trifunovic, Srecko [3 ]
Dalovic, Ivica [6 ]
机构
[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Novi Sad 21000, Serbia
[2] VINCA Inst Nucl Sci, Belgrade 11001, Serbia
[3] Univ Kragujevac, Fac Sci, Dept Chem, Kragujevac 34000, Serbia
[4] Univ Belgrade, Fac Med, Inst Med & Clin Biochem, Belgrade 11001, Serbia
[5] Dept Chem & Pharm Inorgan Chem, D-91058 Erlangen, Germany
[6] Inst Field & Vegetable Crops, Novi Sad 21000, Serbia
关键词
Copper(II) complexes; Pyrazolone; Thiosemicarbazone; X-ray structures; Electrochemistry; Cytotoxicity; CRYSTAL-STRUCTURE; BETA-DIKETONE; PYRAZOLONE;
D O I
10.1016/j.jinorgbio.2011.07.021
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
New polymeric copper(II) complexes with two tridentate ONS thiosemicarbazone ligands containing substituted pyrazolone moiety were synthesized and characterized by means of spectroscopic, electrochemical and crystallographic techniques. While both ligands exist as different tautomers in the solid state and DMSO-d(6) solution, Cu(II) ion coordinates the ligands from the same tautomeric form with square-pyramidal geometry around each Cu atom. In the crystal structures, the copper(II) complex cation forms polymeric chains {[Cu(L)Cl+]}(n) with a bridging chlorine atom. One of the complexes was found to have a significantly higher cytotoxic potential in comparison with cisplatin in inhibition of several cell lines (HL60, REH, C6, L929 and B16). The results obtained on the basis of flow cytometry indicated that apoptosis could be possible mechanism of cell death. (C) 2011 Elsevier Inc. All rights reserved.
引用
收藏
页码:1413 / 1421
页数:9
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