title: Xenobiotic C-sulfonate derivatives; metabolites or metabonates?
abstract: 1. The production of sulfate conjugates is a well-known and established pathway within the field of xenobiotic metabolism. In addition to the usual attachment of a sulfonate grouping via an oxygen atom (O-sulfonates) to yield a sulfate conjugate, so-called "N-sulfates" (N-sulfonates) have been reported and "S-sulfates" (S-sulfonates) mooted to exist. 2. The few examples cited in the literature where the sulfur atom of the sulfonate group was attached directly to a carbon atom of the xenobiotic (C-sulfonates) and subsequently excreted as a metabolite have been collated, examined and reviewed. 3. The potential mechanisms of formation of these C-sulfonates are discussed, both biological and chemical; the potential role of the gut microbiome raised and hopefully by highlighting this curiosity further fruitful investigation will be stimulated.
authors.affiliation: a Computational and Systems Medicine, Department of Surgery and Cancer, Faculty of Medicine, Imperial College London , London , UK.
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Mitchell
mesh_terms: D013431:Sulfates / Q000378:metabolism*; D015262:Xenobiotics / Q000378:metabolism*
chemical_list: D013431:Sulfates; D015262:Xenobiotics
keywords: 2-pyridinethiol-1-oxide; Andrographolide; C-sulfonates; flumipropyn; nitecapone; physalin A