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. 1966 Sep;100(3):745–753. doi: 10.1042/bj1000745

Acetyl transfer in arylamine metabolism

J Booth 1
PMCID: PMC1265210  PMID: 5969287

Abstract

1. N-Hydroxyacetamidoaryl compounds (hydroxamic acids) are metabolites of arylamides, and an enzyme that transfers the acetyl group from these derivatives to arylamines has been found in rat tissues. The reaction products were identified by thin-layer chromatography and a spectrophotometric method, with 4-amino-azobenzene as acetyl acceptor, was used to measure enzyme activity. 2. The acetyltransferase was in the soluble fraction of rat liver, required a thiol for maximum activity and had a pH optimum between 6·0 and 7·5. 3. The soluble fractions of various rat tissues showed decreasing activity in the following order: liver, adrenal, kidney, lung, spleen, testis, heart; brain was inactive. 4. With the exception of aniline and aniline derivatives all the arylamines tested were effective as acetyl acceptors but aromatic compounds with side-chain amino groups were inactive. 5. The N-hydroxyacetamido derivatives of 2-naphthylamine, 4-amino-biphenyl and 2-aminofluorene were active acetyl donors but N-hydroxyacetanilide showed only slight activity. Acetyl-CoA was not a donor. 6. Some properties of the enzyme are compared with those of other acetyltransferases.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BESSMAN S. P., LIPMANN F. The enzymatic transacetylation between aromatic amines. Arch Biochem Biophys. 1953 Sep;46(1):252–254. doi: 10.1016/0003-9861(53)90192-1. [DOI] [PubMed] [Google Scholar]
  2. BOYLAND E., DUKES C. E., GROVER P. L. Carcinogenicity of 2-naphthylhydroxylamine and 2-naphthylamine. Br J Cancer. 1963 Mar;17:79–84. doi: 10.1038/bjc.1963.12. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. BOYLAND E., MANSON D., NERY R. The biochemistry of aromatic amines. 9. Mercapturic acids as metabolites of aniline and 2-naphthylamine. Biochem J. 1963 Feb;86:263–271. doi: 10.1042/bj0860263. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. BRADSHAW L., CLAYSON D. B. Metabolism of two aromatic amines in the dog. Nature. 1955 Nov 19;176(4490):974–975. doi: 10.1038/176974a0. [DOI] [PubMed] [Google Scholar]
  5. BRAY H. G., JAMES S. P., THORPE W. V., WASDELL M. R. Deacetylation of acetamido compounds by tissue extracts. Biochem J. 1950 Oct;47(4):483–488. doi: 10.1042/bj0470483. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Booth J., Boyland E. The biochemistry of aromatic amines. 10. Enzymic N-hydroxylation of arylamines and conversion of arylhydroxylamines into o-aminophenols. Biochem J. 1964 May;91(2):362–369. doi: 10.1042/bj0910362. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Boyland E., Kinder C. H., Manson D. The biochemistry of aromatic amines. 8. Synthesis and detection of di-(2-amino-1-naphthyl) hydrogen phosphate, a metabolite of 2-naphthylamine in dogs. Biochem J. 1961 Jan;78(1):175–179. doi: 10.1042/bj0780175. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. CHOU T. C., LIPMANN F. Separation of acetyl transfer enzymes in pigeon liver extract. J Biol Chem. 1952 May;196(1):89–103. [PubMed] [Google Scholar]
  9. CRAMER J. W., MILLER J. A., MILLER E. C. N-Hydroxylation: A new metabolic reaction observed in the rat with the carcinogen 2-acetylaminofluorene. J Biol Chem. 1960 Mar;235:885–888. [PubMed] [Google Scholar]
  10. Grantham P. H., Weisburger E. K., Weisburger J. H. Dehydroxylation and deacetylation of N-hydroxy-N-2-fluorenylacetamide by rat liver and brain homogenates. Biochim Biophys Acta. 1965 Oct 18;107(3):414–424. doi: 10.1016/0304-4165(65)90185-6. [DOI] [PubMed] [Google Scholar]
  11. Gutmann H. R., Galitski S. B., Foley W. A. N-hydroxy-2-fluorenylbenzamide, an arylhydroxamic acid with high carcinogenic activity. Nature. 1966 Jan 8;209(5019):202–203. doi: 10.1038/209202b0. [DOI] [PubMed] [Google Scholar]
  12. HANDSCHUMACHER R. E., MUELLER G. C., STRONG F. M. An improved enzymatic assay for coenzyme A. J Biol Chem. 1951 Mar;189(1):335–342. [PubMed] [Google Scholar]
  13. IRVING C. C. ENZYMATIC N-HYDROXYLATION OF THE CARCINOGEN 2-ACETYLAMINOFLUORENE AND THE METABOLISM OF N-HYDROXY-2-ACETYLAMINOFLUORENE-9-14C IN VITRO. J Biol Chem. 1964 May;239:1589–1596. [PubMed] [Google Scholar]
  14. JACOBSON K. B. Effect of substrate structure on activity of pigeon liver acetyl transferase. J Biol Chem. 1961 Feb;236:343–348. [PubMed] [Google Scholar]
  15. Jennne J. W. Partial purification and properties of the isoniazid transacetylase in human liver. Its relationship to the acetylation of p-aminosalicylic acid. J Clin Invest. 1965 Dec;44(12):1992–2002. doi: 10.1172/JCI105306. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. KRISCH K. ISOLIERUNG EINER ESTERASE AUS SCHWEINELEBERMIKROSOMEN. Biochem Z. 1963 Aug 14;337:531–545. [PubMed] [Google Scholar]
  17. Kriek E. On the interaction of N-2-fluorenylhydroxylamine with nucleic acids in vitro. Biochem Biophys Res Commun. 1965 Sep 22;20(6):793–799. doi: 10.1016/0006-291x(65)90088-4. [DOI] [PubMed] [Google Scholar]
  18. Lotlikar P. D., Miller E. C., Miller J. A., Margreth A. The enzymatic reduction of the N-hydroxy derivatives of 2-acetylaminofluorene and related carcinogens by tissue preparations. Cancer Res. 1965 Nov;25(10):1743–1752. [PubMed] [Google Scholar]
  19. MILLER E. C., MILLER J. A., HARTMANN H. A. N-Hydroxy-2-acetylaminofluorene: a metabolite of 2-acetylaminofluorene with increased carcinogenic activity in the rat. Cancer Res. 1961 Jul;21:815–824. [PubMed] [Google Scholar]
  20. Miller E. C., McKechnie D., Poirier M. M., Miller J. A. Inhibition of amino acid incorporation in vitro by metabolites of 2-acetylaminofluorene and by certain nitroso compounds. Proc Soc Exp Biol Med. 1965 Nov;120(2):538–541. doi: 10.3181/00379727-120-30583. [DOI] [PubMed] [Google Scholar]
  21. SEAL U. S., GUTMANN H. R. The metabolism of the carcinogen N-(2-fluorenyl) acetamide by liver cell fractions. J Biol Chem. 1959 Mar;234(3):648–654. [PubMed] [Google Scholar]
  22. TABOR H., MEHLER A. H., STADTMAN E. R. The enzymatic acetylation of amines. J Biol Chem. 1953 Sep;204(1):127–138. [PubMed] [Google Scholar]
  23. WEISBURGER J. H. The enzymic deacetylation of the carcinogen 2-acetylaminofluorene and related compounds. Biochim Biophys Acta. 1955 Mar;16(3):382–390. doi: 10.1016/0006-3002(55)90242-0. [DOI] [PubMed] [Google Scholar]
  24. WEISSBACH H., REDFIELD B. G., AXELROD J. The exzymic acetylation of serotonin and other naturally occurring amines. Biochim Biophys Acta. 1961 Nov 25;54:190–192. doi: 10.1016/0006-3002(61)90954-4. [DOI] [PubMed] [Google Scholar]

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