Synthesis, characterization and anticancer evaluation of phosphinogold (I) thiocarbohydrate complexes

Abstract

Several novel thiocarbohydrate phosphinogold(I) complexes were prepared via the reaction of n-gluconamidoalkyl thiol (L1–L7) {where L1–L4 = n-gluconamidoalkyl thiol (n = 1–4),L5– L7 = acetylated n-gluconamidoalkyl thiol (n = 1–3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)] and [Au2Cl2(dppb)], leading to the new gold(I) complexes [Au(L1) (PPh3)] (1–4), [Au(L5)(PPh3)] (5–7), [Au2(L1)2(dppe)] (8–11), [Au2(L5)2(dppx)] (12–14), [(Au2(L6)2) (dppx)] (15–17), [Au2(L7)2(dppx)] (18–20), {where dppe = 1,2-bis(diphenylphosphino)ethane (x = e), dppp = 1,3 is(diphenylphosphino)propane (x = p) and dppb = 1,4-bis-(diphenylphosphino)butane (x = b)}. These gold complexes were characterized by a combination of NMR and infrared spectroscopy, microanalysis and mass spectrometry. Complexes 8,12,14–16 (IC50 values between 0.003 and 1.8 lM) are all active against MCF7, HCT116 and PC3 cells. Complex 8 recorded the highest IC50 value of 0.003 lM against PC3. Complex 14 was found to be selective towards both MCF7 and PC3 cells with a TS value of 142.1, while compounds 15 and 16 were highly selective toward PC3 cells with TS value of 970.0 and 937.5, respectively