Progress in the characterization of gold drugs

As used clinically, Myocrisin appears to contain largely polymeric (Autm)n, in which thiomalate (tm) sulphurs bridge between Au(I) ions, together with small amounts of a more reactive gold-bound thiomalate, and free thiomalate, as well as glycerol, unidentified yellow-products from autoclaving and phenylmercury adducts. Solganal usually contains thioglucose sulphinic acid as an impurity. Auranofin, on the other hand, has been crystallised. It is monomeric and Au(I) is almost linearly coordinated by P and S from triethylphosphine and tetraacetyl-beta-D-thioglucose, the latter adopting the chair conformation in the solid state and in solution. The major reaction of auranofin in acidic aqueous solutions appears to be hydrolysis of the sugar acetyl groups but other products arise if methanol is also present in the medium. NMR methods are used to examine in vitro the partition of auranofin between plasma and blood cells. The displacement of the thioglucose ligand and release of PEt3 from gold as OPEt3 are discussed.