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Chemical and Biological Studies of Dichloro(2-((dimethylamino)methyl)phenyl)gold(III)

Several new organogold(III) derivatives of the type [AuX2(damp)] (damp = o-C6H4CH2NMe2) have been prepared [X = CN, SCN, dtc, or X2 = tm; dtc = R2NCS2 (R = Me (dmtc) or Et (detc)); tm = SCH(CO2)CH2CO2Na] together with [AuCl(tpca)(damp)]Cl (tpca = o-Ph2PC6H4CO2H), [Au(dtc)(damp)]Y (Y = Cl, BPh4) and K[Au-(CN)3(damp)]. The 13C NMR spectra of these and previous derivatives have been fully assigned. In [Au(dtc)2-(damp)] and K[Au(CN)3(damp)], the damp ligand is coordinated only through carbon, as shown by X-ray crystallography and/or NMR. [Au(detc)2(damp)] has space group C2/c, with a = 29.884(4) ?, b = 13.446(2) ?, c = 12.401(2) ?, β = 99.45(3)°, V = 4915 ?3, Z = 8, and R = 0.057 for 1918 reflections. The damp and one detc ligand are monodentate, the other detc is bidentate; in solution, the complex shows dynamic behavior, with the detc ligands appearing equivalent. The crystal structure of [Au(dmtc)(damp)]BPh4 [Pna21, a = 26.149(5) ?, b = 11.250(2) ?, c = 11.921(2) ?, V = 3507 ?3, Z = 4, R = 0.073, 1772 reflections] shows both ligands to be bidentate in the cation, but the two Au-S distances are nonequivaient. The crystal structure of [Au(tm)(damp)] has also been determined [P21/n, a = 18.267(7) ?, b = 9.618(3) ?, c = 18.938(4) ?, β = 113.45(3)°, V = 3053 ?3, Z = 8, R = 0.079, 1389 reflections]. The tm is bound through sulfur and the carboxyl group which allows five-membered ring formation. In all three structures, the trans-influence of the σ-bonded aryl group is apparent. [AuCl2(damp)] has been tested in vitro against a range of microbial strains and several human tumor lines, where it displays differential cytotoxicity similar to that of cisplatin. Against the ZR-75-1 human tumor xenograft, both [AuCl2(damp)] and cisplatin showed limited activity.