Abstract
The metabolism of isomeric amino and acetamidobiphenyls was studied using rat liver microsomal preparations. The aromatic amines were hydroxylated ortho or para to the amino group, whereas the aromatic amides were mainly oxidized in the para position. The carcinogenic amines 3- and 4- aminobiphenyl were converted to hydroxylamines and nitroso compounds. The non-carcinogenic amine 2-aminobiphenyl was resistant to enzymic nitrogen oxidation. The results support the concept that oxidation of aromatic amino groups is a prerequisite for carcinogenic and mutagenic activity.
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References
El-Bayoumy K, La Voie EJ, Tulley-Freiler L, Hecht SS (1981) Effects of ortho-methyl substituents on the mutagenicity of aminobiphenyl and amino aphthalenes. Mutat Res 90: 345–354
Gorrod JW (1964) The carcinogenic effect and metabolism of aromatic amines. Atti del Seminario, Universita da Bari, Casa Editrice Cressati, Bari, Italy 1: 68–98
Gorrod JW (1971) The deacetylation of N-arylacetamides in vitro Biochem J 123: 10 p
Gorrod JW (1979) The metabolism and mode of action of some aromatic amines in relation to carcinogenesis. PhD Thesis, University of London
Gorrod JW, Carey MJ (1970) The metabolism of 2-aminobiphenyl by rats in vivo. Biochem J 119: 52–53
Gorrod JW, Temple DJ, Beckett AH (1975) The metabolism of N-ethyl-N-methylaniline by rabbit liver microsomes: the measurement of metabolites by gas-liquid chromatography. Xenobiotica 5: 453–463
Kiese M, Lenk W (1971) Metabolites of 4-chloroaniline and chloroacetanilides produced by rabbits and pigs. Biochem Pharmacol 20: 379–391
Masson HA, Ioannides C, Gorrod JW, Gibson CG (1983) The role of highly purified cytochrome P-450 isozymes in the activation of 4-aminobiphenyl to mutagenic products in the Ames test. Carcinogenesis 4: 1583–1586
McMahon RE, Turner JC, Whitaker GW (1980) The N-hydroxylation and ring-hydroxylation of 4-aminobiphenyl in vitro by hepatic mono-oxygenases from, rat, mouse, hamster, rabbit and guinea-pig. Xenobiotica 10: 469–481
Uehleke H (1963) N-Hydroxylation of carcinogenic amines in vivo and in vitro with liver microsomes. Biochem Pharmacol 12: 219–221
Weisburger JH, Weisburger EK (1966) Chemicals as causes of cancer. Chem Engineer News 7: 125–142
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Dedicated to Professor Dr. med. Herbert Remmer on the occasion of his 65th birthday
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Bayraktar, N., Kajbaf, M., Jatoe, S.D. et al. The oxidation of isomeric amino and acetamidobiphenyls by rat hepatic microsomal preparations. Arch Toxicol 60, 91–92 (1987). https://doi.org/10.1007/BF00296956
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DOI: https://doi.org/10.1007/BF00296956