Prostaglandin H synthase oxidation of benzidine and o-dianisidine: reduction and conjugation of activated amines by thiols
- 1 January 1985
- journal article
- research article
- Published by Oxford University Press (OUP) in Carcinogenesis: Integrative Cancer Research
- Vol. 6 (4) , 579-583
- https://doi.org/10.1093/carcin/6.4.579
Abstract
Prostaglandin H synthase oxidized the carcinogens benzidine and o-dianisidine to their respective quinonediimines. Analysis of the reaction media by u.v./visible spectroscopy and liquid chromatography with electrochemical and radiochemical detection revealed that these quinonediimines can be both conjugated and reduced by glutathione, cysteine and N-acetyl-cysteine. Analysis of the purified conjugate formed between synthetic benzidinediimine and glutathione by proton magnetic resonance spectroscopy demonstrated the product to be 3-(glutathion-S-yl)-benzidine. This metabolite was also formed during peroxidation of benzidine by prostaglandin H synthase in the presence of excess glutathione. These conjugates may be useful markers of peroxidatic activation of aromatic amines in vivo.This publication has 24 references indexed in Scilit:
- Metabolism of benzidine and benzidine-congener based dyes by human, monkey and rat intestinal bacteriaBiochemical and Biophysical Research Communications, 1982
- Formation and identification of glutathione conjugates from 2-nitrosofluorene and N-hydroxy-2-aminofluoreneChemico-Biological Interactions, 1982
- Cooxidation of benzidine by horseradish peroxidase and subsequent formation of possible thioether conjugates of benzidineBiochemical and Biophysical Research Communications, 1982
- 3-(GLUTATHION-S-YL)ACETAMINOPHEN - A BILIARY METABOLITE OF ACETAMINOPHEN1982
- COVALENT BINDING OF BENZIDINE AND N-ACETYLBENZIDINE TO DNA AT THE C-8 ATOM OF DEOXYGUANOSINE INVIVO AND INVITRO1982
- Metabolism of bisazobiphenyl dyes derived from benzidine, 3,3?-dimethylbenzidine or 3,3?-dimethoxybenzidine to carcinogenic aromatic amines in the dog and rat*1Toxicology and Applied Pharmacology, 1980
- METABOLIC-ACTIVATION OF N-HYDROXY-N,N'-DIACETYLBENZIDINE BY HEPATIC SULFOTRANSFERASE1980
- Chemical and enzymic intermediates in the peroxidation of o-dianisidine by horseradish peroxidase. 1. Spectral properties of the products of dianisidine oxidationBiochemistry, 1979
- Glutathione adducts of N-methyl-4-aminoazobenzene formed in vivo and by reaction of N-benzoyloxy-N-methyl-4-aminoazobenzene with glutathioneChemico-Biological Interactions, 1979
- Purification of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes.Journal of Biological Chemistry, 1976