Arylsulfotransferase IV Catalyzed Sulfation of 1-Naphthalenemethanol
A variety of drugs, carcinogens, and other xenobiotics either contain benzylic alcohol functional groups or are metabolized by hydroxylation at a benzylic carbon. Several studies indicate that the route for formation of reactive metabolites from molecules containing benzylic hydroxyls may proceed via sulfation.1-7 Benzylic sulfate esters have been reported as metabolites of such diverse compounds as 1-methylamino-2-phenylpropan2-ol (an isomer of ephedrine)1, l’-hydroxysafrole,2,5 7,12-dimethylbenzanthracene,3’4 and various mono-and di-nitrotoluenes.6’7 Benzylic sulfates are electrophilic metabolites and can react with cellular nucleophiles due to the ease with which the sulfate acts as a leaving group, and the ability of the aromatic ring to stabilize a positive charge at the benzylic carbon. The ability of these reactive sulfate esters to bind covalently to cellular macromolecules has led to an interest in their role in carcinogenesis and other toxic responses.
KeywordsMethylene Blue Benzylic Alcohol Sodium Succinate Mercapturic Acid Benzylic Carbon
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