Synthesis and Characterization of New Palladium(II) Complexes with Ligands Derived from Furan-2-carbaldehyde and Benzaldehyde Thiosemicarbazone and their in vitro Cytotoxic Activities against Various Human Tumor Cell Lines

被引:10
作者
Hernandez, Wilfredo [1 ]
Paz, Juan [1 ]
Carrasco, Fernando [2 ]
Vaisberg, Abraham [3 ]
Manzur, Jorge [5 ]
Spodine, Evgenia [4 ]
Hennig, Lothar [6 ]
Sieler, Joachim [6 ]
Beyer, Lothar [6 ]
机构
[1] Univ Lima, Fac Ingn Ind, Lima 33, Peru
[2] Univ Nacl Ingn, Fac Ciencias, Rimac Lima, Peru
[3] Univ Peruana Cayetano Heredia, Fac Ciencias & Filosofia, Lab Invest & Desarrollo, Lima 31, Peru
[4] Univ Chile, CEDENNA, Fac Ciencias Quim & Farmaceut, Santiago 8330492, Chile
[5] Univ Chile, CEDENNA, Fac Ciencias Fis & Matemat, Santiago 8370448, Chile
[6] Univ Leipzig, Fak Chem & Mineral, D-04103 Leipzig, Germany
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2010年 / 65卷 / 10期
关键词
Thiosemicarbazone; Palladium(II) Complexes; Crystal Structures; Antitumor/Cytotoxic Activity; TRANSITION-METAL-COMPLEXES; PLATINUM(II) COMPLEXES; CRYSTAL-STRUCTURE; BIOLOGICAL-ACTIVITY; ANTICANCER AGENTS; 2-ACETYL PYRIDINE; VIVO ANTITUMOR; SCHIFF-BASE; DERIVATIVES; NICKEL(II);
D O I
10.1515/znb-2010-1015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
With the ligands 4-phenyl-1-(furan-2-carbaldehyde)thiosemicarbazone, HTSC1, (1), 4-phenyl-1-(5'-phenyl-furan-2-carbaldehyde)thiosemicarbazone, HTSC2 (2), o-methoxy-benzaldehydethiosemicarbazone, HTSC3 (3), and o-cyano-benzaldehydethiosemicarbazone, HTSC4 (4), the corresponding palladium(II) complexes, Pd(TSC1)(2) (5), Pd(TSC2)(2) (6), Pd(TSC3)(2) (7), and Pd(TSC4)(2) (8) were synthesized and characterized by elemental analysis and spectroscopic techniques. The crystal structure of Pd(TSC3)(2) (7) was determined by single-crystal X-ray diffraction. Complex 7 shows a square-planar geometry, where two deprotonated ligands are coordinated to the Pd-II center through the nitrogen and sulfur atoms in a trans arrangement. In vitro antitumor studies against different human tumor cell lines have revealed that the pallaclium(II) complexes 5-8 are more cytotoxic (IC50 values in the range of 0.21-3.79 mu m) than their corresponding ligands (1-4) (> 60 mu m). These results indicate that the antiproliferative activity is enhanced when thiosemicarbazone ligands are coordinated to the metal. Among the studied palladium(II) complexes, 8 exhibits high antitumor activity on K562 chronic myelogenous leukemia cells with a low value of the inhibitory concentration (IC50 = 0.21 mu m).
引用
收藏
页码:1271 / 1278
页数:8
相关论文
共 39 条
[1]  
Abou Melha KS, 2008, J ENZYM INHIB MED CH, V23, P493, DOI [10.1080/14756360701631850 , 10.1080/14756360701631850]
[2]   Appended 1,2-naphthoquinones as anticancer agents 1: synthesis, structural, spectral and antitumor activities of ortho-naphthaquinone thiosemicarbazone and its transition metal complexes [J].
Afrasiabi, Z ;
Sinn, E ;
Chen, JN ;
Ma, YF ;
Rheingold, AL ;
Zakharov, LN ;
Rath, N ;
Padhye, S .
INORGANICA CHIMICA ACTA, 2004, 357 (01) :271-278
[3]   Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D [J].
Afrasiabi, Z ;
Sinn, E ;
Padhye, S ;
Dutta, S ;
Padhye, S ;
Newton, C ;
Anson, CE ;
Powell, AK .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2003, 95 (04) :306-314
[4]  
Agarwal Ram K, 2006, Bioinorg Chem Appl, P59509
[5]   Biological activity of palladium(II) and platinum(II) complexes of the acetone Schiff bases of S-methyl- and S-benzyldithiocarbazate and the X-ray crystal structure of the [Pd(asme)2] (asme=anionic form of the acetone Schiff base of S-methyldithiocarbazate) complex [J].
Ali, MA ;
Mirza, AH ;
Butcher, RJ ;
Tarafder, MTH ;
Keat, TB ;
Ali, AM .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2002, 92 (3-4) :141-148
[6]   Cu(II) complexes with heterocyclic substituted thiosemicarbazones: The case of 5-formyluracil. Synthesis, characterization, X-ray structures, DNA interaction studies, and biological activity [J].
Baldini, M ;
Belicchi-Ferrari, M ;
Bisceglie, F ;
Pelosi, G ;
Pinelli, S ;
Tarasconi, P .
INORGANIC CHEMISTRY, 2003, 42 (06) :2049-2055
[7]   Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Nickel and Copper Complexes of Bis(thiosemicrbazone) [J].
Chandra, Sulekh ;
Raizada, Smriti ;
Tyagi, Monika ;
Gautam, Archana .
BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2007, 2007
[8]   Antibacterial cobalt (II), copper (II), nickel (II) and zinc (II) complexes of mercaptothiadiazole-derived furanyl, thienyl, pyrrolyl, salicylyl and pyridinyl Schiff bases [J].
Chohan, Zahid H. ;
Pervez, Humayun ;
Rauf, Abdul ;
Khan, Khalid M. ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2006, 21 (02) :193-201
[9]   Nickel(II), copper(I) and copper(II) complexes of bidentate heterocyclic thiosemicarbazones [J].
de Lima, RL ;
Teixeira, LRD ;
Carneiro, TMG ;
Beraldo, H .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1999, 10 (03) :184-188
[10]  
Diemer R, 1995, Met Based Drugs, V2, P271, DOI 10.1155/MBD.1995.271