Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines (original) (raw)
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Bioinorganic Chemistry and Applications, 2008
The palladium (II) bis-chelate Pd (L 1−3 ) 2 and platinum (II) tetranuclear Pt 4 (L 4 ) 4 complexes of benzaldehyde thiosemicarbazone derivatives have been synthesized, and characterized by elemental analysis and IR, FAB(+)-mass and NMR ( 1 H, 13 C) spectroscopy. The complex Pd(L 2 ) 2 [HL 2 = m-CN-benzaldehyde thiosemicarbazone] shows a square-planar geometry with two deprotonated ligands (L) coordinated to Pd II through the nitrogen and sulphur atoms in a transarrangement, while the complex Pt 4 (L 4 ) 4 [HL 4 = 4-phenyl-1-benzaldehyde thiosemicarbazone] has a tetranuclear geometry with four tridentate ligands coordinated to four Pt II ions through the carbon (aromatic ring), nitrogen, and sulphur atoms where the ligands are deprotonated at the NH group. The in vitro antitumor activity of the ligands and their complexes was determined against different human tumor cell lines, which revealed that the palladium (II) and platinum (II) complexes are more cytotoxic than their ligands with IC 50 values at the range of 0.07-3.67 μM. The tetranuclear complex Pt 4 (L 4 ) 4 , with the phenyl group in the terminal amine of the ligand, showed higher antiproliferative activity (CI 50 = 0.07-0.12 μM) than the other tested palladium (II) complexes.
Journal of the Brazilian Chemical Society, 2010
Três complexos de Pd II com tiossemicarbazonas N(4)-substituídas foram preparados: [Pd(aptsc) (PPh 3 )](NO 3 )•H 2 O, 1, [Pd(apmtsc)(PPh 3 )](NO 3 ), 2, e [Pd(apptsc)(PPh 3 )](NO 3 )•H 2 O, 3, sendo PPh 3 = trifenilfosfina; Haptsc = 2-acetilpyridina-tiossemicarbazona; Hapmtsc = 2-acetilpiridina-N(4)-metil-tiossemicarbazona e Happtsc = 2-acetilpiridina-N(4)-fenil-tiossemicarbazona. Os complexos foram caracterizados por análise elementar, IR, UV-Vis, 1 H e 31 P{ 1 H} NMR e tiveram suas estruturas cristalinas determinadas por difratometria de raios X em monocristal. Os ligantes tiossemicarbazonatos monoaniônicos atuam de modo tridentado, ligando-se ao metal pelos átomos de nitrogênio piridínico, nitrogênio azometínico e enxofre. A atividade citotóxica frente à linhagem de células tumorais MDA-MB231 (tumor de mama) e a atividade anti-Mycobacterium tuberculosis H 37 Rv ATCC 27294 dos compostos foram investigadas. Os complexos de Pd II mostraram-se altamente ativos contra as células tumorais, com valores de IC 50 em torno de 5 μmol L -1 , enquanto o agente antitumoral em uso clínico cisplatina mostrou-se inativo. Os compostos apresentaram atividade anti-M. tuberculosis significante, com valores de CIM comparáveis ou melhores que aqueles referentes a alguns fármacos usados clinicamente contra tuberculose. Three Pd II complexes were prepared from N(4)-substituted thiosemicarbazones: [Pd(aptsc) (PPh 3 )](NO 3 )•H 2 O, 1, [Pd(apmtsc)(PPh 3 )](NO 3 ), 2, and [Pd(apptsc)(PPh 3 )](NO 3 )•H 2 O, 3,
Journal of Inorganic Biochemistry, 2007
The preparation of new palladium(II) and platinum(II) complexes derived from a-diphenyl ethanedione bis(thiosemicarbazone), 1, and a-diphenyl ethanedione bis(4-ethylthiosemicarbazone), 2, is described. The palladium complexes 3 and 4 and platinum complexes 5 and 6 have been characterized by elemental analyses, fast atom bombardment mass spectrometry (FAB + ) and spectroscopic studies (IR, 1 HNMR). The crystal and molecular structures of the dimeric cyclopalladated compound 4 and the mononuclear platinum complex 6 have been determined by single crystal X-ray diffraction. The cytotoxic activity of the free ligands and palladium and platinum complexes against human A2780 and A2780cisR (acquired resistance to cisplatin) epithelial ovarian carcinoma cells lines is also reported. The IC 50 values for compounds 1, 5 and 6 were found to be higher than that of cisplatin but the maximum antiproliferative activity was similar. Furthermore, the compounds largely retain their activity in the A2780cisR cell line, having a much better resistance factor than cisplatin in the pair of cell lines tested.
Cytotoxic properties of two families of benzaldehyde thiosemicarbazone complexes of palladium
Zenodo (CERN European Organization for Nuclear Research), 2013
Reaction of 4-R-benzaldehy~e thiosernicarbazones (HL-R, where H stands for the dissociable hydrazinic proton-and R (R = OCH 3 , CH 3 , H, Cl and N0 2) for the substituent) with trans-[Pd(PPh 3) 2 CI 2 ] and Na 2 [PdCI 4 ] afford complexes of type [Pd(PPh 3)(L-R)CI] and [Pd(L-R) 2 ] respectively. In vitro cytotoxicity screenings of these complexes along with four human clinical drugs, viz. cisplatin, BCNU, 5-fluorouracil (5-FU) and hydtoxyurea, have been carried out in two human tumor cell lines, viz. pro myelocytic leukemia HL-60 and histiocytic lymphoma U-937. Majority of these complexes show remarkably low IC50 value and are found to be much more cytotoxic than the reference anticancer drugs in both the cell lines. Apoptosis study in HL-60 with two selected complexes from each group shows that at 5 and 10 JLM concentration they induce apoptosis to a greater extent than cisplatin and camptothecin.
Investigational New Drugs, 2019
In vitro cytotoxicity and xanthine oxidase inhibition capabilities were investigated for five palladium (II) chelate complexes. The palladium complexes were synthesized by starting from S-alkyl-thiosemicarbazones where the alkyl component is methyl, ethyl, propyl or butyl. The solid complexes are characterized by elemental analysis and spectroscopic techniques (UV-visible, IR and 1H NMR). In order to be able to verify the N2O2-type thiosemicarbazidato ligand (L2−) structure in the square planar geometry, complex 1 has been studied as a representative by using single crystal X-ray crystallography. The in vitro cytotoxic activity measurements were carried out in HepG2 and Hep3B hepatocellular carcinomas, HCT116 colorectal carcinoma, and 3 T3 mouse fibroblast cell lines. The palladium complexes exhibited notable cytotoxic activities in all cell lines at lower μM concentrations compared to the standard chemicals, cisplatin and allopurinol. IC 50 values were determined between 0.42 ± 0.01 and 12.01 ± 0.37 μg/ml in examining the antixanthine oxidase abilities of the complexes. Two complexes with S-methyl group exhibited a high inhibition activity on the xanthine oxidase. The results indicated that these complexes could be used as active pharmaceutical ingredients.
Inorganic Chemistry Communications, 2019
Six new heteroleptic Pd(II) complexes have been synthesized by reacting equimolar quantities of palladium(II) chloride with the sodium salts of the substituted dithiocarbamates {4benzylpiperazine-1-carbodithioate (1,2), 4-(2-pyridyl)piperazine-1-carbodithioate (3,4) and 4-(2furoyl)piperazine-1-carbodithioate (5,6)), together with the tertiary organophosphines {diphenylp-tolylphosphine (1,3,5) and trip -tolylphosphine (2,4,6)}. These mixed-ligand complexes were characterized by elemental analyses, FT-IR, multinuclear-NMR (1 H, 13 C and 31 P) and singlecrystal X-ray crystallography (1, 2, 4). The symmetrical bidentate coordination mode of the substituted dithiocarbamate ligands around the central Pd(II) ion was confirmed by IR spectroscopy and the pseudo-square-planar geometry of the complexes was established by X-ray crystallography. The anticancer activities of the complexes against various cancer cell lines using staurosporine as the standard drug, were investigated, viz., LU (human lung carcinoma, at