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J Inorg Biochem ; 162: 295-308, 2016 09.
Article in English | MEDLINE | ID: mdl-27138101

ABSTRACT

Substituted semicarbazones/thiosemicarbazones and their copper complexes have been prepared and several single crystal structures examined. The copper complexes of these semicarbazone/thiosemicarbazones were prepared and several crystal structures examined. The single crystal X-ray structure of the pyridyl-substituted semicarbazone showed two types of copper complexes, a monomer and a dimer. We also found that the p-nitrophenyl semicarbazone formed a conventional 'magic lantern' acetate-bridged dimer. Electron Paramagnetic Resonance (EPR) of several of the copper complexes was consistent with the results of single crystal X-ray crystallography. The EPR spectra of the p-nitrophenyl semicarbazone copper complex in dimethylsulfoxide (DMSO) showed the presence of two species, confirming the structural information. Since thiosemicarbazones and semicarbazones have been reported to exhibit anticancer activity, we examined the anticancer activity of several of the derivatives reported in the present study and interestingly only the thiosemicarbazone showed activity while the semicarbazones were not active indicating that introduction of sulphur atom alters the biological profile of these thiosemicarbazones.


Subject(s)
Antineoplastic Agents/chemical synthesis , Coordination Complexes/chemical synthesis , Copper/chemistry , Semicarbazones/chemical synthesis , Thiosemicarbazones/chemical synthesis , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Coordination Complexes/pharmacology , Crystallography, X-Ray , Dimerization , Dimethyl Sulfoxide/chemistry , Electron Spin Resonance Spectroscopy , Epithelial Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Semicarbazones/pharmacology , Solvents/chemistry , Structure-Activity Relationship , Sulfur/chemistry , Thiosemicarbazones/pharmacology
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