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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, Cu^I–SR, from thiophenol, 3-mercapto-1,2-propanediol (MPDH), cysteine (CysH), and glutathione (GSH), were established. BAL displaced Cu(I) from Cu^I–MPD giving Cu^I₂–BAL irrespective of stoichiometry^, while from Cu^I–cys and Cu^I–SG, Cu–BAL were obtained. BAL passivated Cu^I–SPh. The direct reaction of BAL with either Cu(II) or Cu(I) gave insoluble amorphous solids assumed to be Cu^I₂-(oxidized dimeric BAL) or Cu^I₂–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 Cu^I to give Cu^II probably as peroxo complexes.

Keywords

Wilson’s disease Copper(II)Copper(I)cuprous mercaptides British Anti-Lewisite

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Interaction of British Anti-Lewisite (BAL) with Copper(I) and Copper(II) compounds in conjunction with Wilson’s disease

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