Synthesis, superoxide dismutase mimetic and anticancer activities of metal complexes of 2,2-dimethylpentanedioic acid(2dmepdaH2) and 3,3-dimethylpentanedioic acid(3dmepdaH2): X-ray crystal structures of [Cu(3dmepda)(bipy)]2·6H2O and [Cu(2dmepda)(bipy) (EtOH)]2·4EtOH (bipy = 2,2′bipyridine)

Abstract

2,2-dimethylpentanedioic acid (2dmepdaH2) and 3,3-dimethylpentanedioic acid (3dmepdaH2) reacted with copper(II) acetate to give [Cu(2dmepda)(H2O)3]2 (1) and [Cu(3dmepda)(H2O)3]2 (2). Reaction of (1) and (2) with 1,10-phenanthroline and 2,2′-bipyridine yielded [Cu(2dmepda)(phen)(H2O)]20.5phen (3), [Cu(2dmepda)(bipy) (H2O)]2 (4), [Cu(2dmepda)(bipy)(EtOH)]2 · 2EtOH (4A), [Cu(3dmepda)(phen)(H2O)]2 (5), and [Cu(3dmepda)(bipy)(H2O)]2 · (6). The structures of (4A) and (6) each consists of a [Cu(bipy)(dicarboxylate)(solvent)]2 dimer. The superoxide dismutase (SOD) mimetic activity of the novel copper complexes and their manganese analogues was investigated. The dimethyl sulphoxide(DMSO) soluble complexes (1)-(4) and (6) were assessed for their cancer chemotherapeutic potential towards hepatocellular carcinoma and kidney adenocarcinoma cell lines. The 1,10-phenanthroline containing complex [Cu(2dmepda)(phen)(H2O)]20.5phen (3) was the most potent with activity that compares well to that of cisplatin. Copyright © 2006 Michael Devereux et al.