Table of Contents
Metal-Based Drugs
Volume 3, Issue 6, Pages 269-276
http://dx.doi.org/10.1155/MBD.1996.269

Reactions of the Antiarthritic Drug Aurothiomalate With Phenylmercury(II) Compounds: NMR Studies

1School of Physiology and Pharmacology, University of NSW, Sydney 2052, NSW, Australia
2Department of Chemistry, Birkbeck College, University of London, Gordon House and Christopher Ingold Laboratory, 29 Gordon Square, London WC1H OPP, United Kingdom

Received 16 September 1996; Accepted 23 September 1996

Copyright © 1996 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Clinical formulations of the antiarthritic drug aurothiomalate sometimes contain phenylmercury(ll) compounds as antimicrobial preservative agents and, in the presence of para-chloromercuri-benzoate, aurothiomalate is a potent inhibitor of collagenase. By H1 NMR spectroscopy, para-hydroxymercuribenzoate and para-hydroxymercuriphenylsulphonate were shown to react with aurothiomalate by complexing only with the terminal thiomalate of aurothiomalate oligomers, thereby converting them to ring complexes. The reaction was also detected by UV spectroscopy. The arylmercury complexes produced no change in the bulk of the thiomalate residues of aurothiomalate indicating considerable stability of the polymeric structure of aurothiomalate in which each gold is bound to two thiolate residues. The potent inhibition of the mercurial induced collagenase activity may be due either to aurothiomalate or to a complex formed between the terminal thiomalate residues with the arylmercurial. The arylmercury complexes may be unsuitable as antimicrobials in solutions of aurothiomalate because of complexation with the terminal thiomalate residues.