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

Authors:
  • BHBrian P. Howe
    Brian P. Howe
  • JWJonathan P. Wright
    Jonathan P. Wright
  • JMJürgen Mack
    Jürgen Mack
  • RPRobin G. Pritchard
    Robin G. Pritchard
  • RBRobert G. Buckley
    Robert G. Buckley
  • AEAmanda M. Elsome
    Amanda M. Elsome
  • SFSimon P. Fricker
    Simon P. Fricker
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Abstract
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) Å, b = 13.446(2) Å, c = 12.401(2) Å, β = 99.45(3)o, V = 4915 Å3, 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) Å, b = 11.250(2) Å, c = 11.921(2) Å, V = 3507 Å3, Z = 4, R = 0.073, 1772 reflections] shows both ligands to be bidentate in the cation, but the two Au−S distances are nonequivalent. The crystal structure of [Au(tm)(damp)] has also been determined [P21/n, a = 18.267(7) Å, b = 9.618(3) Å, c = 18.938(4) Å, β = 113.45(3)o, V = 3053 Å3, 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.

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