title: Synthesis, characterization and biological activities of semicarbazones and their copper complexes.
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.
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia. Electronic address: t.venkatachalam@uq.edu.au.
authors.forename: Taracad K
authors.initials: TK
authors.lastname: Venkatachalam
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: Paul V
authors.initials: PV
authors.lastname: Bernhardt
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: Chris J
authors.initials: CJ
authors.lastname: Noble
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Fletcher
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: Gregory K
authors.initials: GK
authors.lastname: Pierens
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: Kris J
authors.initials: KJ
authors.lastname: Thurecht
authors.affiliation: Centre for Advanced Imaging, School of Chemistry University of Queensland, St. Lucia, Brisbane 4072, Australia.
authors.forename: David C
authors.initials: DC
authors.lastname: Reutens
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000494:pharmacology; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019281:Dimerization; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D004847:Epithelial Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D012664:Semicarbazones / Q000138:chemical synthesis* / Q000494:pharmacology; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000737:chemistry; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D012664:Semicarbazones; D012997:Solvents; D013882:Thiosemicarbazones; D013455:Sulfur; D003300:Copper; D004121:Dimethyl Sulfoxide
keywords: Biological activity; Characterization; Copper complex; Semicarbazones; Synthesis; X-ray crystallography