Neutral gold complexes with tridentate SNS thiosemicarbazide ligands.
Na[AuCl(4)]·2H(2)O reacts with tridentate thiosemicarbazide ligands, H(2)L1, derived from N-[N',N'-dialkylamino(thiocarbonyl)]benzimidoyl chloride and thiosemicarbazides under formation of air-stable, green [AuCl(L1)] complexes. The organic ligands coordinate in a planar SNS coordination mode. Small amounts of gold(I) complexes of the composition [AuCl(L3)] are formed as side-products, where L3 is an S-bonded 5-diethylamino-3-phenyl-1-thiocarbamoyl-1,2,4-triazole. The formation of the triazole L3 can be explained by the oxidation of H(2)L1 to an intermediate thiatriazine L2 by Au(3+), followed by a desulfurization reaction with ring contraction. The chloro ligands in the [AuCl(L1)] complexes can readily be replaced by other monoanionic ligands such as SCN(-) or CN(-) giving [Au(SCN)(L1)] or [Au(CN)(L1)] complexes. The complexes described in this paper represent the first examples of fully characterized neutral Gold(III) thiosemicarbazone complexes. All the [AuCl(L1)] compounds present a remarkable cell growth inhibition against human MCF-7 breast cancer cells. However, systematic variation of the alkyl groups in the N(4)-position of the thiosemicarbazone building blocks as well as the replacement of the chloride by thiocyanate ligands do not considerably influence the biological activity. On the other hand, the reduction of Au(III) to Au(I) leads to a considerable decrease of the cytotoxicity.
Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, São Carlos-São Paulo, Brazil.
Pedro I da S
PI
Maia
Hung Huy
HH
Nguyen
Daniela
D
Ponader
Adelheid
A
Hagenbach
Silke
S
Bergemann
Ronald
R
Gust
Victor M
VM
Deflon
Ulrich
U
Abram
D045744:Cell Line, Tumor; D006046:Gold / Q000737:chemistry*; D006801:Humans; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D012663:Semicarbazides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D014961:X-Ray Diffraction
D008024:Ligands; D012663:Semicarbazides; C005151:thiosemicarbazide; D006046:Gold