Synthesis, characterization and antiproliferative activity of amino- and DMSO complexes of platinum(II) containing l-carnitine

• l-Carnitine was used as mono or bidentate anionic ligand for Pt(II).
• Five new l-carnitine/amino (NH3, 1,2-DACH) complexes and four l-carnitine/DMSO complexes were prepared and characterized.
• The antiproliferative activity of three representative complexes were assayed against three human cancer cell lines.

l-Carnitine, a biomolecule able to cross the blood–brain barrier exploiting specific transporters, behaves as mono or bidentate anionic ligand for Pt(II) in the new amino complexes cis-[Pt(l-carnitine-O)2(NH3)2](BF4)2 (1), cis-[PtCl(l-carnitina-O)(NH3)2]BF4 (2), [Pt(l-carnitine-O,O′)(1,2-DACH)]BF4 (3), [Pt(l-carnitine-O)2(1,2-DACH)](BF4)2 (4), and [PtCl(l-carnitine-O)(1,2-DACH)](BF4) (5). Four complexes with DMSO have been also prepared and characterized: the synthetic intermediate [Pt(CO3)(DMSO)2] (6), [Pt(l-carnitine-O,O′)(DMSO)2]BF4 (7), cis-[Pt(l-carnitine-O)2(DMSO)2](BF4)2 (8) and cis-[PtCl(l-carnitine-O)(DMSO)2]BF4, (9).The antiproliferative activity of three representative complexes 1, 5 and 7 has been assayed against three human cancer cell lines A2780, K562 and SKOV3, and it was found comparable to that of the parent active compounds cis-[PtCl2(1,2-DACH)] and cisplatin.

l-Carnitine was coordinated to Pt(II) as a mono or bidentate anionic ligand giving a group of cis-L2Pt(II) complexes (2L = 2NH3, 1,2-DACH or 2DMSO).The antiproliferative activity of three representative complexes (1, 5 and 7) was assayed against three human cancer cell lines. It was found that l-carnitine does not reduce the remarkable activity of the precursors cis-[PtCl2(1,2-DACH)] and cisplatin and therefore this natural molecule deserves to be investigated as a carrier of Pt across the blood–brain barrier, exploiting its specific transporters.Figure optionsDownload as PowerPoint slide