Molecular Mechanisms of Polymorphism in Acetylating Enzymes for Arylamines and N-Hydroxyarylamines in Hamster Liver

References

• Evans D. A. N-Acetyltransferase. Pharmacol. Ther. 1989; 42: 157–234
   PubMed Web of Science ®Google Scholar
• Weber W. W., Hein D. W. N-acetylation pharmacogenetics. Pharm. Rev. 1985; 37: 25–79
   PubMed Web of Science ®Google Scholar
• Glowinski I. B., Radke H. E., Weber W. W. Genetic variation in N-acetylation of carcinogen arylamines by human and rabbit liver. Mol. Pharmacol 1978; 14: 940–949
   PubMed Web of Science ®Google Scholar
• Lower G. M. J., Bryan G. T. Enzymatic N-acetylation of carcinogenic aromatic amines by liver cytosol of species displaying different organ susceptibilities. Biochem. Pharmacol. 1973; 22: 1581–1588
   PubMed Web of Science ®Google Scholar
• Shinohara A., Yamazoe Y., Saito K., Kamataki T., Kato R. Species differences in the N-acetylation by liver cytosol of mutagenic heterocyclic aromatic amines in protein pyrolysates. Carcinogenesis 1984; 5: 683–686
   PubMed Web of Science ®Google Scholar
• Hein D. W., Omichinski J. G., Brewer J. A., Weber W. W. A unique pharmacogenetic expression of the N-acetylation polymorphism in the inbred hamster,. J. Pharm. Exp. Ther. 1982; 220: 8
   PubMed Web of Science ®Google Scholar
• Hein D. W., Kirlin W. G., Ferguson R. J., Weber W. W. Inheritance of liver N-acetyltransferase activity in the rapid and slow acetylator inbred hamster. J. Pharm. Exp. Ther. 1985; 233: 584–587
   PubMed Web of Science ®Google Scholar
• Kato R., Yamazoe Y. N-Hydroxyarylamine O-acetyltransferase in mammalian livers and Salmonella. Carcinogenic and Mutagenic Responses to Aromatic amines and Nitroarenes, M. King, L. J. Romano, D. Shuetzle. Elsevier Science Publishing, New York 1988; 125–136
   Google Scholar
• Kato R., Yamazoe Y. Further metabolic activations of mutagenic and carcinogenic N-hydroxy arylamine by conjugating enzymes. Xenobiotic Metabolism and Disposition, R. Kato, R. W. Estabrook, M. N. Cayen. Taylor & Francis, London 1989; 383–391
   Google Scholar
• Ozawa S., Abu-Zeid M., Kawakubo Y., Toyama S., Yamazoe Y., Kato R. Monomorphic and polymorphic isozymes of arylamine N-acetyltransferase in hamster liver: purification of the isozymes and genetic basis of N-acetylation polymorphism. Carcinogenesis 1990; 11: 2137–2144
   PubMed Web of Science ®Google Scholar
• Abu-Zeid M., Nagata K., Miyata M., Ozawa S., Fukuhara M., Yamazoe Y., Kato R. An arylamine acetyltransferase (AT-I) from Syrian golden hamster liver: Cloning, complete nucleotide sequence, and expression in mammalian cells. Mol. Carcinogenesis 1991; 4: 81–88
   PubMed Web of Science ®Google Scholar
• Nagata K., Ozawa S., Miyata M., Shimada M., Yamazoe Y., Kato R. Primary structure and molecular basis of polymorphic appearance of a hamster acetyltransferase, AT-II. Pharmacogenetics 1994; 4: 91–100
   PubMedGoogle Scholar
• King C. M., Glowinski I. B. Acetylation, deacetylation and acyltransfer. Environ. Health Perspec 1983; 49: 43–50
   PubMed Web of Science ®Google Scholar
• Yamazoe Y., Shimada M., Kamataki T., Kato R. Covalent binding of N-hydroxy-Trp-P-2 to DNA by cytosolic proline-depen-dent system. Biochem. Biophys. Res. Commun. 1982; 107: 165–172
   PubMed Web of Science ®Google Scholar
• Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. DNA binding of N-hydroxy-Trp-P-2 and Af-hydroxy-Glu-P-1 by acetyl-CoA dependent enzyme in mammalian liver cytosol. Carcinogenesis 1985; 6: 305–307
   PubMed Web of Science ®Google Scholar
• Shinohara A., Saito K., Yamazoe Y., Kamataki T., Kato R. Acetyl coenzyme A-dependent activation of N-hydroxy derivative of carcinogenic arylamines: Mechanism of activation, species difference, tissue distribution and acetyl donor specificity. Cancer Res. 1986; 46: A362–W61
   PubMedGoogle Scholar
• Flammang T. J., Westra J. G., Kadlubar F. F., Beland F. A. DNA adducts formed from the probable proximate carcinogen, N-hydroxy-3,2′-dimethyl-4-aminobiophenyl, by acid catalysis or 5-acetyl coenzyme A-dependent enzymatic esterification. Carcinogenesis 1985; 6: 251–258
   PubMed Web of Science ®Google Scholar
• Flammang T. J., Kadlubar F. F. Acetyl coenzyme A-dependent metabolic activation and A'-hydroxy-3,2′-dimethyl-4-aminobiphenyl and several carcinogenic N-hydroxyarylamines in relation to tissue and species differences, other acetyldonors, and arylhydroxamic acid-dependent acyltransferases. Carcinogenesis 1986; 7: 919–926
   PubMed Web of Science ®Google Scholar
• Saito K., Shinohara A., Kamataki T., Kato R. N-Hydroxy-arylamine O-acetyltransferase in hamster liver: Identity with arylhydroxamic acid, N, O-acetyltransferase and arylamine N-acetyltrans-ferase. J. Biochem. 1986; 99: 1689–1697
   PubMed Web of Science ®Google Scholar
• Weber W. W. Commentary: The molecular basis of hereditary acetylation polymorphisms. Drug Metab. Dispos. 1986; 14: 377–381
   PubMed Web of Science ®Google Scholar
• Hanna P., Banks P. B., Marhevka V. C. Suicide inactivation of hamster hepatic arylhydroxamic acid N, O-acyltransferase A selective probe of Af-acetyltransferase multiplicity. Mol. Pharmacol. 1982; 21: 159–165
   PubMed Web of Science ®Google Scholar
• Smith T. J., Hanna P. E. A'-Acetytransferase multiplicity and the bioactivation of N-arylhydroxamic acids by hamster hepatic and intestinal enzymes. Carcinogenesis 1986; 7: 697–702
   PubMed Web of Science ®Google Scholar
• Hein D. W., Kirlin W. G., Ogolla F., Trinidad A., Thompson L. K., Ferguson R. J. The role of acetylator genotype on hepatic and extrahepatic acetylation, deacetylation, and sulfation of 2-aminofluorene, 2-acetylaminofluorene, and N-hydroxy-2-acerylaminofluorene in the inbred hamster. Drug Metab. Dispos. 1986; 14: 566–573
   PubMed Web of Science ®Google Scholar
• Hein D. W., Flammang T. J., Kirlin W. G., Trinidad A., Ogolla F. Acetylator genotype-dependent metabolic activation of carcinogenic N-hydroxyarylamines by S-acetyl coenzyme A-dependent enzymes of inbred hamster tissue cytosols: Relationship to arylamine N-acetyltransferase. Carcinogenesis 1987; 8: 1767–1774
   PubMed Web of Science ®Google Scholar
• Trinidad A., Hein D. W., Rustan T. D., Ferguson R. J., Miller L. S., Bucher K. D., Kirlin W. G., Ogolla F., Andrews A. F. Purification of hepatic polymorphic arylamine N-acetyltransferase from homozygous rapid acetylator inbred hamster: Identity with polymorphic N-hydroxyarylamine-O-acetyltransferase. Cancer Res. 1990; 50: 7942–7949
   PubMed Web of Science ®Google Scholar
• Kawakubo Y., Manabe S., Yamazoe Y., Nishikawa T., Kato R. Properties of cutaneous acetyltransferase catalyzing N- and O-acetylation of carcinogenic arylamines and N-hydroxyarylamine. Biochem. Pharmacol 1988; 37: 265–270
   PubMed Web of Science ®Google Scholar
• Hein D. W., Rustan T. D., Bucher K. D., Miller L. S. Polymorphic and monomorphic expression of arylamine carcinogen N-acetyltransferase isozymes in tumor target organ cytosols of Syrian hamsters congenic at the polymorphic acetyltransferase locus. J. Pharmacol. Exp. Ther. 1991; 259: 699–704
   PubMed Web of Science ®Google Scholar
• Kawakubo Y., Yamazoe Y., Kato R., Nishikawa T. High capacity of human skin for N-acetylation of arylamines. Skin Pharmacol. 1990; 3: 180–185
   PubMedGoogle Scholar
• Hein D. W. Genetic polymorphism and cancer susceptibility: Evidence concerning acetyltransferases and cancer of the urinary bladder. BioEssays 1988; 9: 200–204
   PubMed Web of Science ®Google Scholar
• Hein D. W., Doll M. A., Gray K., Rustan T. D., Ferguson R. J. Metabolic activation of N-hydroxy-2-aminofluorene and N-hydroxy-2-acetylaminofluorene by monomorphic N-acetyltransferase (NAT1) and polymorphic N-acetyltransferase (NAT2) in colon cytosols of Syrian hamsters congenic at the NAT2 locus. Cancer Res. 1993; 53: 509–514
   PubMed Web of Science ®Google Scholar
• Saito K., Yamazoe Y., Kamataki T., Kato R. Mechanism of activation of proximate mutagens in Ames' tester strains: The acetyl CoA-dependent enzyme in Salmonella typhimurium TA98 deficient in TA98/1,8-DNP6 catalyzes DNA binding as the cause of mutagenicity. Biochem. Biophys. Res. Commun. 1983; 116: 141–147
   PubMed Web of Science ®Google Scholar
• Saito K., Shinohara A., Kamataki T., Kato R. Metabolic activation of mutagenic N-hydroxyarylamines by O-acetyltransferase in Salmonella typhimurium TA98. Arch. Biochem. Biophys. 1985; 239: 286–295
   PubMed Web of Science ®Google Scholar
• Yamazoe Y., Abu-Zeid M., Dawei G., Staiano N., Kato R. Enzymatic acetylation and sulfation of N-hydroxyarylamines in bacteria and rat livers. Carcinogenesis 1989; 10: 1675–1679
   PubMed Web of Science ®Google Scholar
• Ando M., Shindo Y., Fujita M., Ozawa S., Yamazoe Y., Kato R. A new Salmonella tester strain expressing a mammalian acetyl-transferase shows high sensitivity for arylamines. Mutat. Res. 1993; 292: 155–163
   PubMed Web of Science ®Google Scholar
• Martell K. J., Levy G. N., Weber W. W. Cloned mouse N-acetyltransferases–enzymatic properties of expressed Nat-1 and Nat-2 gene products. Mol. Pharmacol. 1992; 42: 265–272
   PubMed Web of Science ®Google Scholar
• Deguchi T. Sequences and expression of alleles of polymorphic arylamine N-acetyltransferase of human liver. J. Biol. Chem. 1992; 267: 18140–18147
   PubMed Web of Science ®Google Scholar
• Martell K. J., Vatsis K. P., Weber W. W. Molecular genetic basis of rapid and slow acetylation in mice. Mol. Pharmacol. 1991; 40: 218–227
   PubMed Web of Science ®Google Scholar
• Allaben W. T., King C. M. The purification of rat liver aryl-hydroxamic acid N,O-acyltransferase. J. Biol. Chem. 1984; 259: 12128–12134
   PubMedGoogle Scholar
• Reeves P. T., Kinnear B. F., Minchin R. F., Ilett K. F. Immunological evidence for N-acetyltransferase isozymes in the rabbit. Mol. Pharmacol. 1991; 39: 42–48
   PubMed Web of Science ®Google Scholar
• Andres H. H., Vogel R. S., Tarr G. E., Johnson L., Weber W. W. Purification, physicochemical, and kinetic properties of liver acetyl-CoA:arylamine N-acetyltransferase from rapid acetylator rabbits. Mol. Pharmacol. 1987; 31: 446–456
   PubMed Web of Science ®Google Scholar
• Jenne J. W., Orser M. Partial purification and properties of the isoniazid transacetylase in human liver. Its relationship to the acetylation of p-aminosalicyclic acid. J. Clin. Invest. 1965; 44: 1992–2002
   PubMed Web of Science ®Google Scholar
• Grant D. M., Blum M., Meyer U. A. Polymorphisms of N-acetyltransferase genes. Xenobiotica 1992; 22: 1073–1081
   PubMed Web of Science ®Google Scholar
• Blum M., Grant D. M., Demierre A., Meyer U. A. Nucleotide sequence of a full-length cDNA for arylamine N-acetyltransferase from rabbit liver,. Nucleic Acids Res. 1989; 17: 3589
   PubMed Web of Science ®Google Scholar
• Blum M., Heim M., Meyer U. A. Nucleotide sequence of rabbit NAT1 encoding monomorphic arylamine AT-acetyltransferase,. Nucleic Acids Res. 1990; 18: 5287
   PubMed Web of Science ®Google Scholar
• Grant D. M., Blum M., Demierre A., Meyer U. A. Nucleotide sequence of an intronless gene for a human arylamine N-acetyltransferase related to polymorphic drug acetylation. Nucleic Acids Res 1989; 17: 3978
   PubMed Web of Science ®Google Scholar
• Ohsako S., Deguchi T. Cloning and expression of cDNAs for polymorphic and monomorphic arylamine N-acetyltransferases from human liver. J. Biol. Chem. 1990; 265: 4630–4634
   PubMed Web of Science ®Google Scholar
• Frymoyer J. W., Jacox R. F. Studies of genetically controled sulfadiazine acetylation in rabbit livers: Possible identification of the heterozygous trait. J. Lab. Clin. Med. 1963; 62: 905–909
   PubMed Web of Science ®Google Scholar
• Hein D. W., Hirata M., Glowinski I. B., Weber W. W. Biochemical evidence for the coexistence of monomorphic and polymorphic N-acetyltransferase activities on a common protein in rabbit liver. J. Pharm. Exp. Ther. 1982; 220: 1–7
   PubMed Web of Science ®Google Scholar
• Blum M., Grant D. M., Demierre A., Meyer U. A. N-Acetylation pharmacogenetics: A gene deletion causes absence of arylamine N-acetyltransferase in liver of slow acetylator rabbits. Proc. Natl. Acad. Sci. USA 1989; 86: 9554–9557
   PubMed Web of Science ®Google Scholar
• Vatsis K. P., Martell K. J., Weber W. W. Diverse point mutations in the human gene for polymorphic N-acetyltransferase. Proc. Natl. Acad. Sci. USA 1991; 88: 6333–6337
   PubMed Web of Science ®Google Scholar