Host –guest interactions involving platinum anticancer agents. DNA binding and cytotoxicity of a β-cyclodextrin-adamantane-Pt(IV) complex

A Pt(IV) complex, 1-adamantanemethylamine–Pt(IV), 2, a potential prodrug of the Pt(II) anticancer agent cisplatin was synthesized by tethering 1-adamantanemethylamine to oxoplatin using a dicarboxylate linker. The host–guest inclusion complex of 2 with β-cyclodextrin, is less toxic toward neuroblastoma SK-N-SH cells than cisplatin. Reduction of the inclusion complex with ascorbic acid produces a Pt(II) product that binds to and unwinds pBR322 form I DNA in a manner that is similar to that of cisplatin.