Towards a more selective analogue of oxaliplatin: Synthesis of [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)]

A novel oxaliplatin analogue, [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)], boldiplatin, has been synthesized by the coordination of the boldine derivative 3-carboxypredicentrinate to the corresponding platinum(II) moiety in 5.8% overall yield. The complex was fully characterized and biologically evaluated in vitro. Boldiplatin was compared with its parent drug oxaliplatin, showing equal activity over four human tumor cell lines (MCF-7, MDA-MB-231, PC-3 and HT-29) and a tenfold decrease in toxicity over a non-tumor cell line (DHF). This selectivity makes boldiplatin a good candidate for further evaluations to assess its potential as antitumor drug.

Boldiplatin, a novel oxaliplatin analogue, was synthesized from the platinum(II) precursor K2[PtCl4] and the boldine derivate 3-carboxipredicentrine. The in vitro cell viability assays demonstrate that both compounds exhibit the same activity over four distinct human tumor cell lines, and that boldiplatin shows less toxicity over a non-tumor cell line.Figure optionsDownload as PowerPoint slideHighlights
► A platinum complex, using a boldine derivative as ligand, was synthesized.
► Boldiplatin exhibits similar biological activity than oxaliplatin.
► Boldiplatin has greater selectivity for some cancer cell lines than oxaliplatin.