Anticancer cyclometalated [Au(III)m(C(wedge)N(wedge)C)mL]n+ compounds: Synthesis and cytotoxic properties

Chemistry : a European Journal
Carrie Ka-Lei LiChi-Ming Che

Abstract

A series of cyclometalated gold(III) compounds [Au(m)(C(wedge)N(wedge)C)mL]n+ (m = 1-3; n = 0-3; HC(wedge)N(wedge)CH = 2,6-diphenylpyridine) was prepared by ligand substitution reaction of L with N-donor or phosphine ligands. The [Au(m)(C(wedge)N(wedge)C)mL]n+ compounds are stable in solution in the presence of glutathione. Crystal structures of the gold(III) compounds containing bridging bi- and tridentate phosphino ligands reveal the presence of weak intramolecular pi pi stacking between the [Au(C(wedge)N(wedge)C)]+ units. Results of MTT assays demonstrated that the [Au(m)(C(wedge)N(wedge)C)mL]n+ compounds containing nontoxic N-donor auxiliary ligands (2) exert anticancer potency comparable to that of cisplatin, with IC50 values ranging from 1.5 to 84 microM. The use of [Au(C(wedge)N(wedge)C)(1-methylimidazole)]+ (2 a) as a model compound revealed that the gold(III)-induced cytotoxicity occurs through an apoptotic cell-death pathway. The cell-free interaction of 2 a with double-stranded DNA was also examined. Absorption titration showed that 2 a binds to calf-thymus DNA (ctDNA) with a binding constant of 4.5 x 10(5) dm3 mol(-1) at 298 K. Evidence from gel-mobility-shift assays and viscosity measurements supports an intercalat...Continue Reading

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