Water-soluble phosphanes derived from 1,3,5-triaza-7-phosphaadamantane and their reactivity towards gold(I) complexes

Abstract

New water-soluble phosphanes derived from 1,3,5-triaza-7-phosphaadamantane, namely, [PTA-R]Br (R = -CH2C≡CH, -CH2CONH 2, -CH2COOH), are described. Coordination of these phosphanes and their previously reported counterparts (R = -CH2CN, -CH2Ph and -CH2COOMe) to gold(I) salts gives water-soluble derivatives with chlorido, bromido or pentafluorophenyl coligands. The luminescence properties of all new compounds have been studied in the solid state and compared with the respective free PTA ligands. [PTA-CH 2Ph]Br, [PTA-CH2COOMe]Br and [AuBr(PTA-CH 2Ph)]Br have also been characterised by X-ray diffraction analysis. Some of the new gold(I) compounds exhibit strong antiproliferative effects in the human ovarian carcinoma cell line A2780 and its cisplatin-resistant variant (A2780cisR). A balanced relationship between lipophilicity and hydrophilicity is found in these derivatives, with distribution coefficients (log D 7.4) that range from 0.14 to -0.40. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.