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Studies on synthesis, structure, and antitumor activity of Pt(II) complexes containing 1,2-diamino-1,2-dideoxy-D-glucitol.

An attempt was made to develop new water-soluble antitumor Pt(II) complexes by introducing hydroxyl groups into a carrier ligand, 1, 2-diamino-1, 2-dideoxy-D-glucitol (1, 2-DAG), and their structures were determined by 13C nuclear magnetic resonance and circular dicroism spectral analyses. Only [Pt(NO3)2(1, 2-DAG)] and [Pt(SO4)(1, 2-DAG)] exhibited marginal effects against leukemia L1210 in vivo, among compounds with various leaving groups.The unexpectedly low antitumor activity of Pt(II) complexes containing 1, 2-DAG was investigated in in vitro experiments. The Pt(II) complexes of 1, 2-DAG showed the same binding mode with calf-thymus deoxyribonucleic acid (DNA) as cis-diamminedichloroplatinum(II), but inhibition of DNA synthesis in L1210 cells in vitro was not observed even at the concentration of 100 μM [PtCl2(1, 2-DAG)] or [Pt(oxalato)(1, 2-DAG)]. Consideration of the Pt contents taken into the cells indicated that the Pt(II) complexes have difficulty in passing through the cell membranes, which might account for the low antitumor effects observed in vivo.