Summary
The velocity of the N- and p-hydroxylation of aniline and N-ethylaniline by NADPH-dependent hydroxylases in guinea pig liver microsomes was found to be as high as in rabbit liver microsomes. Microsomes prepared from cat livers were less active.
The effect of 2,4-dichlorophenol, p-chloromercuribenzoate, semicarbazide, and 8-hydroxyquinoline on the microsomal hydroxylations was observed to be not uniform in the microsomes of the species studied.
Carbon monoxide inhibited the p-hydroxylation of N-ethylaniline by the microsomes prepared from the livers of rabbits, guinea pigs, dogs, and rats. The N-hydroxylation of N-ethylaniline by microsomes from rat's liver was inhibited like the p-hydroxylation by carbon monoxide. The N-hydroxylation by dog and guinea pig microsomes was scarcely, if at all, inhibited by the same carbon monoxide pressure. These enzymes showed a lower affinity for oxygen than the N-hydroxylating enzyme in rat microsomes and the p-hydroxylating enzymes.
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References
Gornall, A. G., C. J. Bardawill, and M. M. David: Determination of serum proteins by means of the biuret reaction. J. biol. Chem. 177, 751 (1949).
Irving, C. C.: N-Hydroxylation of the carcinogen 2-acetyl-aminofluorene by rabbit liver microsomes. Biochim. biophys. Acta (Amst.) 65, 564 (1962).
— Enzymatic N-hydroxylation of the carcinogen 2-acetylaminofluorene-9-carbon-14 in vitro. J. biol. Chem. 239, 1595 (1964).
Jagow, R. von, H. Kampffmeyer, and M. Kiese: The preparation of microsomes. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. (in press) (1965).
Kampffmeyer, H., and M. Kiese: Unpublished experiments (1961).
— Einige Eigenschaften der Anilin-hydroxylierenden Enzyme in Mikrosomen. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 244, 375 (1963).
— Further factors affecting the hydroxylation of aniline and some of its derivatives by liver microsomes. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 246, 397 (1964a).
— The hydroxylation of aniline and N-ethylaniline by microsomal enzymes at low oxygen pressures. Biochem. Z. 339, 454 (1964b).
— The effect of carbon monoxide on the hydroxylation of aniline and N-ethylaniline by microsomal enzymes. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 250, 1 (1965).
Kiese, M., and E. Rauscher: Isolation of phenylhydroxylamine produced from N-ethylaniline by microsomal enzymes. Biochem. Z. 338, 1 (1963).
Miller, J. A., J. W. Cramer, and E. C. Miller: The N- and ring-hydroxylation of 2-acetylaminofluorene during carcinogenesis in the rat. Cancer Res. 20, 950 (1960).
Miller, E. C., J. A. Miller, and H. A. Hartmann: N-Hydroxy-2-acetylaminofluorene a metabolite of acetylaminofluorene with increased carcinogenic activity in the rat. Cancer Res. 21, 815 (1961).
Miller, J. A., C. S. Wyatt, E. C. Miller, and H. K. Hartmann: The N-hydroxylation of 4-acetylaminobiphenyl by the rat and dog and the strong carcinogenicity of N-hydroxy-4-acetylaminobiphenyl in the rat. Cancer Res. 21, 1465 (1961).
Quinn, G. P., J. Axelrod, and B. B. Brodie: Species, strain and sex differences in metabolism of hexobarbitone, amidopyrine, antipyrine and aniline. Biochem. Pharmacol. 1, 152 (1958).
Siegert, M., B. Alsleben, W. Liebenschütz u. H. Remmer: Unterschiede in der mikrosomalen Oxydation und Acetylierung von Arzneimitteln bei verschiedenen Arten und Rassen. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 247, 509 (1964).
Weisburger, E. K., and J. H. Weisburger: Chemistry, carcinogenicity, and metabolism of 2-fluorenamine and related compounds. Advanc. Cancer Res. 5, 331 (1958).
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Appel, W., Graffe, W., Kampffmeyer, H. et al. Species differences in the hydroxylation of aniline and N-ethylaniline by liver microsomes. Naunyn - Schmiedebergs Arch 251, 88–94 (1965). https://doi.org/10.1007/BF00245732
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DOI: https://doi.org/10.1007/BF00245732