Book chapter
Arylsulfotransferase IV Catalyzed Sulfation of 1-Naphthalenemethanol
Biological Reactive Intermediates III, pp.415-422
Advances in Experimental Medicine and Biology, Springer US
1986
DOI: 10.1007/978-1-4684-5134-4_40
PMID: 3464166
Abstract
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.
Details
- Title: Subtitle
- Arylsulfotransferase IV Catalyzed Sulfation of 1-Naphthalenemethanol
- Creators
- Michael W. Duffel - University of IowaMaria N. Janss - University of Iowa
- Resource Type
- Book chapter
- Publication Details
- Biological Reactive Intermediates III, pp.415-422
- Publisher
- Springer US; Boston, MA
- Series
- Advances in Experimental Medicine and Biology
- DOI
- 10.1007/978-1-4684-5134-4_40
- PMID
- 3464166
- ISSN
- 0065-2598
- Language
- English
- Date published
- 1986
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984303163502771
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