Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl)butane]platinum(II) Complexes: Synthesis and Antitumor Activity against MCF-7 and MDA-MB 231 Breast Cancer and LnCaP/FGC Prostate Cancer Cell Lines

Enantiomerically pure 1, 2‐diamino‐1‐(4‐fluorophenyl)butanes were synthesized by stereoselective procedures. The enantiomeric purity was determined by 1H NMR spectroscopy after derivatization with (1R)‐myrtenal. For the coordination to platinum, the diamines were reacted with K2PtI4. Reaction with Ag2SO4 yielded the respective sulfatoplatinum(II) complexes, which were converted into the dichloroplatinum(II) complexes by treatment with 2 N HCl. The influence of the configuration and the kind of leaving group on the antitumor activity was studied on the MCF‐7 and MDA‐MB 231 breast cancer cell lines, as well as on the LnCaP/FGC prostate cancer cell line. It was demonstrated that the dichloroplatinum(II) complexes were more active than the respective diiodoplatinum(II) derivatives. Conversion into the sulfatoplatinum(II) complexes further enhanced the antiproliferative effects. The configuration determined the antitumor effects, dependent on the cell line used: MCF‐7: (R, R) > (S, S) > (R, S) > (S, R); MDA‐MB 231: (S, S) > (R, R) > (R, S) = (S, R); LnCaP/FGC: (S, S) > (R, R) > (R, S) > (S, R).