Copper(ii) and palladium(ii) complexes with cytotoxic and antibacterial activity

A.M. Krause-Heuer, P. Leverett, J.R. Aldrich-Wright, A. Bolhuis

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The synthesis of eight square pyramidal copper complexes with general structure [Cu(I )(A )H O] , where IL represents various methylated 1,10-phenanthrolines, and AL represents either 1S,2S- or 1R,2R-diaminocyclohexane, is reported, with the complexes synthesised as both the perchlorate and chloride salts. The crystal structures of [Cu(1,10-phenanthroline)(1S,2S-diaminocyclohexane](ClO ) ·H O and [Cu(5,6-dimethyl-1,10-phenanthroline)(1S, 2S-diaminocyclohexane](ClO ) ·1.5H O are reported. Four square planar palladium complexes with general structure [Pd(I )(A )]Cl have also been synthesised. These complexes were synthesised in order to investigate the structureactivity relationship against both cancer cell lines and bacterial cultures. The copper complexes display anticancer activity similar to cisplatin and 1,10-phenanthroline (phen) in the L1210 murine leukaemia cell line. Methylation of the phen increased the copper complex cytotoxicity by approximately four-fold, compared with the non-methylated complex. No significant difference in activity was observed by altering the chirality of the diaminocyclohexane ligand. The copper complexes demonstrated antibacterial activity against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli; however, high levels of toxicity (30-60% of death) were observed in the nematode Caenorhabditis elegans. The copper complexes have also been shown to act as DNA nucleases, with the ability to cleave plasmid DNA in the presence of hydrogen peroxide. The palladium complexes all have half maximal inhibitory concentration (IC ) values of ∼10μM in the L1210 cell line, with no significant difference in the cytotoxicity of any of the compounds tested. Minimal antibacterial activity of the palladium complexes was observed.
Original languageEnglish
Pages (from-to)860-873
Number of pages14
JournalAustralian Journal of Chemistry
Volume65
Issue number7
DOIs
Publication statusPublished - 1 Jan 2012

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