Chemical structure of the adducts formed by the oxidation of benzidine in the presence of phenols
Journal Article
·
· Carcinogenesis (N.Y.); (United States)
Bioactivation of carcinogens by peroxidases has received increasing attention since the discovery of the oxidation of carcinogens by prostaglandin hydroperoxidase. Benzidine and 3,5,3',5'-tetramethylbenzidine are oxidized by horseradish peroxidase and prostaglandin synthase to two-electron oxidation products (di-imines). Di-imines readily react with the phenolic anti-oxidant butylated hydroxyanisole to form adducts. In this paper, we have studied the oxidation of benzidine by horseradish peroxidase in the presence of phenolic compounds and characterized the resultant benzidine/phenol adducts. A benzidine/2,6-dimethylphenol adduct was isolated and characterized by mass spectrometry and high field n.m.r. The reaction of (/sup 14/C)benzidine in the presence of horseradish peroxidase and phenol yielded only the benzidine/phenol adduct. Our results indicate that the benzidine/phenol adducts are analogous to the indoaniline dyes, differing only in substitution of a biphenyl group for a benzene ring. The reaction of benzidine di-imine with endogenous phenols may represent a new pathway for detoxication, removing potentially harmful metabolites of benzidine.
- Research Organization:
- Laboratory of Pulmonary Function and Toxicology, National Institute of Environmental Health Sciences, Research Triangle Park, NC
- OSTI ID:
- 5984149
- Journal Information:
- Carcinogenesis (N.Y.); (United States), Journal Name: Carcinogenesis (N.Y.); (United States) Vol. 3:10; ISSN CRNGD
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
550201 -- Biochemistry-- Tracer Techniques
560301* -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINES
AROMATICS
BENZIDINE
BIOLOGICAL EFFECTS
BIOLOGICAL PATHWAYS
CARBON 14 COMPOUNDS
CARBOXYLIC ACIDS
DETOXIFICATION
ENZYMES
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
METABOLIC ACTIVATION
METABOLISM
METABOLITES
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDOREDUCTASES
PEROXIDASES
PHENOLS
PORPHYRINS
STRUCTURAL CHEMICAL ANALYSIS
TRACER TECHNIQUES
560301* -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINES
AROMATICS
BENZIDINE
BIOLOGICAL EFFECTS
BIOLOGICAL PATHWAYS
CARBON 14 COMPOUNDS
CARBOXYLIC ACIDS
DETOXIFICATION
ENZYMES
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
METABOLIC ACTIVATION
METABOLISM
METABOLITES
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDOREDUCTASES
PEROXIDASES
PHENOLS
PORPHYRINS
STRUCTURAL CHEMICAL ANALYSIS
TRACER TECHNIQUES