Affiliations: [a] Department of Chemistry, University of Patras, Patras, Greece
| [b] Department of Chemistry, School of Sciences, University of Sussex, Falmer, Brighton, East Sussex, UK
Correspondence:
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Corresponding author: Panayiotis V. Ioannou, Department of Chemistry, University of Patras, 26504 Patras, Greece. Fax: +30 2610 997118; E-mail: [email protected].
Abstract: The chemistry of British Anti-Lewisite (BAL) and copper in relation to the therapeutic action for the treatment of Wilson’s disease was studied by reacting selected Cu(I) and Cu(II) compounds with a range of thiol compounds. Optimum conditions for the preparation of cuprous mercaptides, CuI–SR, from thiophenol, 3-mercapto-1,2-propanediol (MPDH), cysteine (CysH), and glutathione (GSH), were established. BAL displaced Cu(I) from CuI–MPD giving CuI2–BAL irrespective of stoichiometry, while from CuI–cys and CuI–SG, Cu–BAL were obtained. BAL passivated CuI–SPh. The direct reaction of BAL with either Cu(II) or Cu(I) gave insoluble amorphous solids assumed to be CuI2-(oxidized dimeric BAL) or CuI2–BAL, respectively, that could not be completely analyzed or solubilized under various conditions. Thus, the detection of elevated copper in the urine of Wilson’s disease patients treated with BAL may not be directly due to the solubilization of endogenous copper by BAL. Cuprous mercaptides are easily autoxidized by attack of O2 to CuI to give CuII probably as peroxo complexes.
Keywords: Wilson’s disease, Copper(II), Copper(I), cuprous mercaptides, British Anti-Lewisite
