Oxidative activation of benzidine and its derivatives by peroxidases
Journal Article
·
· Environ. Health Perspect.; (United States)
Benzidine (4,4'-diaminobiphenyl) is a known human carcinogen; exposure to this substance resulted in an epidemic of bladder cancer among workers in the dye industry in Europe and north America. The chemical or enzymatic oxidation of benzidine proceeds via a radical cation detectable by electron spin resonance. Peroxidase-catalyzed oxidation of benzidine generates reactive electrophiles which readily form adducts with phenol and thiol compounds. The structures of these novel metabolites are described. Peroxidases, including prostaglandin synthase, catalyze benizidine binding to protein and nucleic acid; the nature of the resulting adducts is unknown. The relevance of these processes to benzidine carcinogenesis in vivo is the subject of research and debate. A central question remains: is benzidine activated in extrahepatic target tissues such as bladder epithelium, or transported to these tissues following hepatic oxidative metabolism. 62 references.
- Research Organization:
- Univ. of Guelph, Ontario
- OSTI ID:
- 5176308
- Journal Information:
- Environ. Health Perspect.; (United States), Journal Name: Environ. Health Perspect.; (United States) Vol. 64; ISSN EVHPA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400104 -- Spectral Procedures-- (-1987)
560306* -- Chemicals Metabolism & Toxicology-- Man-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AMINES
AROMATICS
BENZIDINE
BIOCHEMICAL REACTION KINETICS
BLADDER
BODY
CARCINOGENS
CATALYSIS
CATIONS
CELL TRANSFORMATIONS
CHARGED PARTICLES
CHEMICAL ACTIVATION
DYES
ELECTRON SPIN RESONANCE
ENZYMES
EUROPE
HYDROXY COMPOUNDS
IONS
KINETICS
MAGNETIC RESONANCE
METABOLITES
NORTH AMERICA
NUCLEIC ACIDS
OCCUPATIONAL DISEASES
ONCOGENIC TRANSFORMATIONS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANS
OXIDOREDUCTASES
PEROXIDASES
PHENOLS
PROSTAGLANDINS
PROTEINS
RADICALS
REACTION KINETICS
RESONANCE
STRUCTURAL CHEMICAL ANALYSIS
THIOLS
URINARY TRACT
400104 -- Spectral Procedures-- (-1987)
560306* -- Chemicals Metabolism & Toxicology-- Man-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AMINES
AROMATICS
BENZIDINE
BIOCHEMICAL REACTION KINETICS
BLADDER
BODY
CARCINOGENS
CATALYSIS
CATIONS
CELL TRANSFORMATIONS
CHARGED PARTICLES
CHEMICAL ACTIVATION
DYES
ELECTRON SPIN RESONANCE
ENZYMES
EUROPE
HYDROXY COMPOUNDS
IONS
KINETICS
MAGNETIC RESONANCE
METABOLITES
NORTH AMERICA
NUCLEIC ACIDS
OCCUPATIONAL DISEASES
ONCOGENIC TRANSFORMATIONS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANS
OXIDOREDUCTASES
PEROXIDASES
PHENOLS
PROSTAGLANDINS
PROTEINS
RADICALS
REACTION KINETICS
RESONANCE
STRUCTURAL CHEMICAL ANALYSIS
THIOLS
URINARY TRACT