Complexes of platinum and palladium with β-diketones and DMSO: Synthesis, characterization, molecular modeling, and biological studies

被引:30
作者
do Couto Almeida, J. [1 ]
Marzano, I. M. [2 ]
Silva de Paula, F. C. [2 ]
Pivatto, M. [1 ]
Lopes, N. P. [3 ]
de Souza, P. C. [4 ]
Pavan, F. R. [4 ]
Formiga, A. L. B. [5 ]
Pereira-Maia, B. C. [2 ]
Guerra, W. [1 ]
机构
[1] Univ Fed Uberlandia, Inst Quim, BR-38400902 Uberlandia, MG, Brazil
[2] Univ Fed Minas Gerais, Dept Quim, BR-31 27090 Belo Horizonte, MG, Brazil
[3] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, NPPNS, BR-14040903 Ribeirao Preto, SP, Brazil
[4] Univ Estadual Paulista, Dept Ciencias Biol, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP, Brazil
[5] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Metal complexes; Molecular modeling; beta-Diketones; Mycobacterium tuberculosis; Cytotoxic activity; GAUSSIAN-TYPE BASIS; ORBITAL METHODS; VIBRATIONAL-SPECTRA; CRYSTAL-STRUCTURE; CYTOTOXICITY; ANTIBACTERIAL; TAUTOMERISM; DERIVATIVES; EXTRACTION; RESISTANT;
D O I
10.1016/j.molstruc.2014.07.023
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
This work reports on the synthesis and characterization of new complexes of the type MCl(L)DMSO], where L = 4,4,4-trifluoro-1-phenyl-1,3-butanedione (HTPB) or 4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione (HTTA) and M = Pt2+ or Pd2+. These complexes were characterized by elemental analyses, conductivity measurements, FT-IR, UV-Vis, high-resolution mass spectra (HRESIMS) and TG/DTA. In the complexes, the metallic ions bind to beta-diketone via the oxygen atoms and to DMSO molecule via sulfur atom. The structures of complexes were optimized and theoretical data showed good agreement with the experimental results. The cytotoxic activity of the compounds was evaluated in a chronic myelogenous leukemia cell line. The platinum complexes were more cytotoxic than the free ligands and carboplatin and are promising candidates for further investigations. As example, the compound [PtCl(TPB)(DMSO)] inhibits the growth of K562 cells with an IC50 value equal to 2.5 mu M, Furthermore, microbiological assays against Mycobacterium tuberculosis showed that all complexes exhibit low cytotoxicity against this bacterial strain while the free ligands exhibited MIC values of approximately 10 mu g mL(-1). (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:370 / 376
页数:7
相关论文
共 48 条
[1]   Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].
Adamo, C ;
Barone, V .
JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170
[2]  
[Anonymous], An Open-Source Java Viewer for Chemical Structures in 3D
[3]   Vibrational spectra and theoretical studies of tautomerism and hydrogen bonding in the violuric acid and 6-amino-5-nitrosouracil system [J].
Bonacin, J. A. ;
Formiga, A. L. B. ;
de Melo, V. H. S. ;
Toma, H. E. .
VIBRATIONAL SPECTROSCOPY, 2007, 44 (01) :133-141
[4]   Enhancing lipophilicity as a strategy to overcome resistance against platinum complexes? [J].
Buss, Irina ;
Garmann, Dirk ;
Galanski, Mathea S. ;
Weber, Guenther ;
Kalayda, Ganna V. ;
Keppler, Bernhard K. ;
Jaehde, Ulrich .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2011, 105 (05) :709-717
[5]   A silver complex with tryptophan: Synthesis, structural characterization, DFT studies and antibacterial and antitumor assays in vitro [J].
Carvalho, Marcos A. ;
de Paiva, Raphael E. F. ;
Bergamini, Fernando R. G. ;
Gomes, Alexandre F. ;
Gozzo, Fabio C. ;
Lustri, Wilton R. ;
Formiga, Andre L. B. ;
Shishido, Silvia M. ;
Ferreira, Carmen V. ;
Corbi, Pedro P. .
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1031 :125-131
[6]  
Cesar ET, 2007, B KOREAN CHEM SOC, V28, P295
[7]   Synthesis, spectral, and thermal characterizations of Ni(II) and Cu(II) β-diketone complexes with thenoyltrifluoroacetone ligand [J].
Chen, Zhimin ;
Wu, Yiqun ;
Huang, Fuxin ;
Gu, Donghong ;
Gan, Fuxi .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2007, 66 (4-5) :1024-1029
[8]   Ruthenium metallopharmaceuticals [J].
Clarke, MJ .
COORDINATION CHEMISTRY REVIEWS, 2002, 232 (1-2) :69-93
[9]   EXTRACTION OF FE(III), CU(II), CO(II), NI(II) AND PB(II) WITH THENOYLTRIFLUOROACETONE USING THE TERNARY SOLVENT SYSTEM WATER ETHANOL METHYLISOBUTYLKETONE [J].
DASILVA, JF ;
MARTINS, W .
TALANTA, 1992, 39 (10) :1307-1312
[10]   Synthesis, spectroscopic characterization, DFT studies and antibacterial assays of a novel silver(I) complex with the anti-inflammatory nimesulide [J].
de Paiva, Raphael E. F. ;
Abbehausen, Camilla ;
Gomes, Alexandre F. ;
Gozzo, Fabio C. ;
Lustri, Wilton R. ;
Formiga, Andre L. B. ;
Corbi, Pedro P. .
POLYHEDRON, 2012, 36 (01) :112-119