Sulfenic acids as reactive intermediates in xenobiotic metabolism.
Sulfenic acid reactive intermediates are formed during the oxidation of cysteine residues of proteins and play key roles in enzyme catalysis, redox homeostasis and regulation of cell signalling. However few data are presently available on the formation and fate of sulfenic acids as reactive intermediates during the metabolism of xenobiotics. This article is a review of the xenobiotic metabolism situations in which the intermediate formation of a sulfenic acid has been reported. Formation of these intermediates has been either proposed on the basis of the isolation of products possibly deriving from sulfenic acids or shown after trapping of the sulfenic acid by specific nucleophiles. This review indicates the different mechanisms by which a sulphur-containing xenobiotic can be metabolized with the intermediate formation of a sulfenic acid. It also indicates the different possible fates of these sulfenic acids that have been reported in the literature. Finally, it discusses the possible implications of the formation of xenobiotic-derived sulfenic acid reactive metabolites in pharmacology and toxicology.
Mansuy
Daniel
D
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR 8601 CNRS, Université Paris Descartes, 45 rue des Saints-pères, Paris Cedex 06, France. daniel.mansuy@parisdescartes.fr
Dansette
Patrick M
PM
D000818:Animals; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D006801:Humans; D010084:Oxidation-Reduction; D013434:Sulfenic Acids / Q000737:chemistry / Q000378:metabolism*; D013457:Sulfur Compounds / Q000737:chemistry / Q000378:metabolism*; D015262:Xenobiotics / Q000737:chemistry / Q000378:metabolism*
D013434:Sulfenic Acids; D013457:Sulfur Compounds; D015262:Xenobiotics; D003577:Cytochrome P-450 Enzyme System