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Chemical Compound Review

Anilinum     aniline

Synonyms: Benzidam, ANILINE, Aminophen, Anilina, Arylamine, ...
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Disease relevance of aniline

  • Bacterial luciferase and NAD(P)H: FMN oxidoreductase isolated from Beneckea harveyi were covalently linked via diazotization to arylamine porous glass beads which had been cemented onto plain glass rods [1].
  • We examined arylamine substrate and acetyl coenzyme A cofactor affinities, and the N-acetyltransferase catalytic activities of the wild-type and 14 different mutant or chimeric human NAT2 alleles expressed in an Escherichia coli JM105 expression system [2].
  • Salmonella typhimurium strains expressing human arylamine N-acetyltransferases: metabolism and mutagenic activation of aromatic amines [3].
  • Acetylator genotype-dependent expression by the human colon of arylamine N-acetylation capacity, catalyzed by acetyl coenzyme A-dependent N-acetyltransferase(s) (EC (NAT), may be an important risk factor in the initiation of colorectal cancer [4].
  • In aromatic amine-induced rat hepatomas, the aldehyde dehydrogenase (AIDH) phenotype is qualitatively and quantitatively different from that of normal liver [5].

High impact information on aniline

  • The activation of these, and also some arylamine drugs, involves N-hydroxylation, usually by cytochrome P450 (P450) [6].
  • These results demonstrate considerable tissue, species, and compound specificity for the metabolic activation of aromatic amines and provide further evidence in support of bladder activation as a mechanism of aromatic amine-induced bladder cancer [7].
  • The aromatic amine 2,4-toluenediamine was fed at levels of 50 and 100 ppm to inbred, barrier-raised F344 rats for 2 years [8].
  • Previously, we showed that NAT2 polymorphisms did not influence bladder cancer risk among Chinese workers exposed exclusively to benzidine (BZ), suggesting that NAT2 N-acetylation is not a critical detoxifying pathway for this aromatic amine [9].
  • These data strongly suggest that defective arylamine N-acetylation in the rabbit model is caused by a gene deletion resulting in an absence of specific mRNA and NAT enzyme protein [10].

Chemical compound and disease context of aniline


Biological context of aniline

  • The polymorphic expression of these acetylation activities may be important risk factors in human susceptibility to bladder cancer from arylamine carcinogens [16].
  • Significantly greater mean apparent Vmax levels were found in colons from rapid as compared to intermediate acetylators (1.5-3-fold) (P less than 0.001) and intermediate as compared to slow (2.5-3-fold) (P less than 0.005) acetylator phenotypes for the four arylamine substrates [4].
  • Aberrant crypts, the earliest morphologically evident preneoplastic lesions in chemical colon carcinogenesis, were measured in rapid and slow acetylator congenic Syrian hamsters administered 3,2' -dimethyl-4-aminobiphenyl, an aromatic amine colon carcinogen, to investigate the specific role of the acetylator genotype (NAT2) in colon carcinogenesis [17].
  • In this paper we report the construction and use of new tester strains of S. typhimurium that express high levels of functional human arylamine N-acetyltransferases, NAT1 and NAT2, retaining characteristic arylamine substrate specificities that are distinct from those of the bacterial enzyme [3].
  • The genetic predisposition of rapid acetylators to colorectal cancers suggests localized metabolic activation of arylamine carcinogen metabolites by polymorphic N-acetyltransferase (NAT2) in colon tissues [18].

Anatomical context of aniline

  • This radioligand, which possesses an arylamine moiety, may then be covalently incorporated into the receptor binding subunit (58,000 Mr peptide) of the frog erythrocyte membranes by the use of the bifunctional photoactive crosslinker N-succinimidyl-6-(4'-azido-2'- nitrophenylamino)hexanoate (SANAH) [19].
  • Expression of arylamine N-acetyltransferases in pre-term placentas and in human pre-implantation embryos [20].
  • Four of the bladder cytosols had mean activities significantly (P less than 0.01) higher (approximately 10-fold) than the mean NAT activities of the other five bladder cytosols towards each arylamine carcinogen [16].
  • Unscheduled DNA synthesis (UDS)-inducing activity was used as a parameter to estimate the abilities of rat mammary epithelial cells and urothelial cells from various species to activate carcinogenic aromatic amine derivatives [21].
  • The arylhydroxamic acid acyltransferase, an enzyme that promotes the introduction of arylamine groups into nucleic acids, is greater in the stomach, small intestine, colon, and lung of the Sprague-Dawley rat than in comparable tissues of Fischer animals [22].

Associations of aniline with other chemical compounds


Gene context of aniline

  • The single coding exons of the cloned genes encoding two human arylamine N-acetyltransferases (NAT1 and NAT2) were amplified by expression-cassette polymerase chain reaction and subcloned into the tac promoter-based phagemid vector pKEN2 for production of the recombinant proteins in Escherichia coli strain XA90 [27].
  • Human N-acetyltransferase type 1 (NAT1) catalyses the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens [28].
  • Combined analyses of different alleles of carcinogenic aromatic amine-activating phase II enzymes were applied to urothelial cancer risk for the first time and showed the highest risk combination of ST1A3 and NAT2 alleles [29].
  • Renal interstitial fibrosis based on the interstitial area stained with Aniline-blue or Sirius red solution was significantly attenuated in the obstructed kidney of Smad3(-/-) mice when compared with that of Smad3(+/+) mice [30].
  • N-acetyltransferase activity toward the aromatic amine carcinogen 4-aminobiphenyl and O-acetyltransferase activity toward its proximate metabolite N-hydroxy-4-aminobiphenyl were both present in tissue cytosols of WT mice but were undetectable in Nat2 KO mice [31].

Analytical, diagnostic and therapeutic context of aniline


  1. Immobilization of bacterial luciferase and FMN reductase on glass rods. Jablonski, E., DeLuca, M. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  2. Molecular genetics of human polymorphic N-acetyltransferase: enzymatic analysis of 15 recombinant wild-type, mutant, and chimeric NAT2 allozymes. Hein, D.W., Ferguson, R.J., Doll, M.A., Rustan, T.D., Gray, K. Hum. Mol. Genet. (1994) [Pubmed]
  3. Salmonella typhimurium strains expressing human arylamine N-acetyltransferases: metabolism and mutagenic activation of aromatic amines. Grant, D.M., Josephy, P.D., Lord, H.L., Morrison, L.D. Cancer Res. (1992) [Pubmed]
  4. Acetylator genotype-dependent expression of arylamine N-acetyltransferase in human colon cytosol from non-cancer and colorectal cancer patients. Kirlin, W.G., Ogolla, F., Andrews, A.F., Trinidad, A., Ferguson, R.J., Yerokun, T., Mpezo, M., Hein, D.W. Cancer Res. (1991) [Pubmed]
  5. Expression of the tumor aldehyde dehydrogenase phenotype during 2-acetylaminofluorene-induced rat hepatocarcinogenesis. Lindahl, R., Evces, S., Sheng, W.L. Cancer Res. (1982) [Pubmed]
  6. Cytochrome P450 activation of arylamines and heterocyclic amines. Kim, D., Guengerich, F.P. Annu. Rev. Pharmacol. Toxicol. (2005) [Pubmed]
  7. Organ, species, and compound specificity in the metabolic activation of primary aromatic amines. Poupko, J.M., Radomski, T., Santella, R.M., Radomski, J.L. J. Natl. Cancer Inst. (1983) [Pubmed]
  8. Carcinogenicity and chronic toxicity of 2,4-toluenediamine in F344 rats. Cardy, R.H. J. Natl. Cancer Inst. (1979) [Pubmed]
  9. The impact of interindividual variation in NAT2 activity on benzidine urinary metabolites and urothelial DNA adducts in exposed workers. Rothman, N., Bhatnagar, V.K., Hayes, R.B., Zenser, T.V., Kashyap, S.K., Butler, M.A., Bell, D.A., Lakshmi, V., Jaeger, M., Kashyap, R., Hirvonen, A., Schulte, P.A., Dosemeci, M., Hsu, F., Parikh, D.J., Davis, B.B., Talaska, G. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  10. N-acetylation pharmacogenetics: a gene deletion causes absence of arylamine N-acetyltransferase in liver of slow acetylator rabbits. Blum, M., Grant, D.M., Demierre, A., Meyer, U.A. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  11. The structure of arylamine N-acetyltransferase from Mycobacterium smegmatis--an enzyme which inactivates the anti-tubercular drug, isoniazid. Sandy, J., Mushtaq, A., Kawamura, A., Sinclair, J., Sim, E., Noble, M. J. Mol. Biol. (2002) [Pubmed]
  12. Acetylator phenotype and lupus erythematosus. Uetrecht, J.P., Woosley, R.L. Clinical pharmacokinetics. (1981) [Pubmed]
  13. Glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4, 5-b]pyridine by human microsomal UDP-glucuronosyltransferases: identification of specific UGT1A family isoforms involved. Nowell, S.A., Massengill, J.S., Williams, S., Radominska-Pandya, A., Tephly, T.R., Cheng, Z., Strassburg, C.P., Tukey, R.H., MacLeod, S.L., Lang, N.P., Kadlubar, F.F. Carcinogenesis (1999) [Pubmed]
  14. Azido- and nitro-PhIP, relatives of the heterocyclic arylamine and food mutagen PhIP--mechanism of their mutagenicity in Salmonella. Wild, D., Watkins, B.E., Vanderlaan, M. Carcinogenesis (1991) [Pubmed]
  15. Characterization of the topa quinone cofactor in amine oxidase from Escherichia coli by resonance Raman spectroscopy. Moënne-Loccoz, P., Nakamura, N., Steinebach, V., Duine, J.A., Mure, M., Klinman, J.P., Sanders-Loehr, J. Biochemistry (1995) [Pubmed]
  16. Polymorphic expression of acetyl coenzyme A-dependent arylamine N-acetyltransferase and acetyl coenzyme A-dependent O-acetyltransferase-mediated activation of N-hydroxyarylamines by human bladder cytosol. Kirlin, W.G., Trinidad, A., Yerokun, T., Ogolla, F., Ferguson, R.J., Andrews, A.F., Brady, P.K., Hein, D.W. Cancer Res. (1989) [Pubmed]
  17. Acetylator genotype (NAT2)-dependent formation of aberrant crypts in congenic Syrian hamsters administered 3,2'-dimethyl-4-aminobiphenyl. Feng, Y., Wagner, R.J., Fretland, A.J., Becker, W.K., Cooley, A.M., Pretlow, T.P., Lee, K.J., Hein, D.W. Cancer Res. (1996) [Pubmed]
  18. 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. Hein, D.W., Doll, M.A., Gray, K., Rustan, T.D., Ferguson, R.J. Cancer Res. (1993) [Pubmed]
  19. The beta-adrenergic receptor: rapid purification and covalent labeling by photoaffinity crosslinking. Shorr, R.G., Heald, S.L., Jeffs, P.W., Lavin, T.N., Strohsacker, M.W., Lefkowitz, R.J., Caron, M.G. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  20. Expression of arylamine N-acetyltransferases in pre-term placentas and in human pre-implantation embryos. Smelt, V.A., Upton, A., Adjaye, J., Payton, M.A., Boukouvala, S., Johnson, N., Mardon, H.J., Sim, E. Hum. Mol. Genet. (2000) [Pubmed]
  21. Induction of repair synthesis of DNA in mammary and urinary bladder epithelial cells by N-hydroxy derivatives of carcinogenic arylamines. Wang, C.Y., Yamada, H., Morton, K.C., Zukowski, K., Lee, M.S., King, C.M. Cancer Res. (1988) [Pubmed]
  22. Comparative effects of strain, species, and sex on the acyltransferase- and sulfotransferase-catalyzed activations of N-hydroxy-N-2-fluorenylacetamide. King, C.M., Olive, C.W. Cancer Res. (1975) [Pubmed]
  23. Biological activity of catecholamines covalently linked to synthetic polymers: proof of immobilized drug theory. Verlander, M.S., Venter, J.C., Goodman, M., Kaplan, N.O., Saks, B. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  24. Retinal rhythms in chicks: circadian variation in melantonin and serotonin N-acetyltransferase activity. Hamm, H.E., Menaker, M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  25. Metabolism and binding of benzo(a)pyrene and 2-acetylaminofluorene by short-term organ cultures of human and rat bladder. Moore, B.P., Hicks, R.M., Knowles, M.A., Redgrave, S. Cancer Res. (1982) [Pubmed]
  26. Metabolic activation of carcinogenic aromatic amines by dog bladder and kidney prostaglandin H synthase. Wise, R.W., Zenser, T.V., Kadlubar, F.F., Davis, B.B. Cancer Res. (1984) [Pubmed]
  27. Site-directed mutagenesis of recombinant human arylamine N-acetyltransferase expressed in Escherichia coli. Evidence for direct involvement of Cys68 in the catalytic mechanism of polymorphic human NAT2. Dupret, J.M., Grant, D.M. J. Biol. Chem. (1992) [Pubmed]
  28. Functional polymorphism of the human arylamine N-acetyltransferase type 1 gene caused by C190T and G560A mutations. Butcher, N.J., Ilett, K.F., Minchin, R.F. Pharmacogenetics (1998) [Pubmed]
  29. Association of genotypes of carcinogen-activating enzymes, phenol sulfotransferase SULT1A1 (ST1A3) and arylamine N-acetyltransferase NAT2, with urothelial cancer in a Japanese population. Ozawa, S., Katoh, T., Inatomi, H., Imai, H., Kuroda, Y., Ichiba, M., Ohno, Y. Int. J. Cancer (2002) [Pubmed]
  30. Smad3 deficiency attenuates renal fibrosis, inflammation,and apoptosis after unilateral ureteral obstruction. Inazaki, K., Kanamaru, Y., Kojima, Y., Sueyoshi, N., Okumura, K., Kaneko, K., Yamashiro, Y., Ogawa, H., Nakao, A. Kidney Int. (2004) [Pubmed]
  31. N-acetyltransferase (nat) 1 and 2 expression in nat2 knockout mice. Loehle, J.A., Cornish, V., Wakefield, L., Doll, M.A., Neale, J.R., Zang, Y., Sim, E., Hein, D.W. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  32. Bentiromide as a test of exocrine pancreatic function in adult patients with pancreatic exocrine insufficiency. Determination of appropriate dose and urinary collection interval. Toskes, P.P. Gastroenterology (1983) [Pubmed]
  33. Growth and structural properties of epithelial cell cultures established from normal rat liver and chemically induced hepatomas. Weinstein, I.B., Orenstein, J.M., Gebert, R., Kaighn, M.E., Stadler, U.C. Cancer Res. (1975) [Pubmed]
  34. Human liver arylacetamide deacetylase. Molecular cloning of a novel esterase involved in the metabolic activation of arylamine carcinogens with high sequence similarity to hormone-sensitive lipase. Probst, M.R., Beer, M., Beer, D., Jenö, P., Meyer, U.A., Gasser, R. J. Biol. Chem. (1994) [Pubmed]
  35. Quantification of the heterocyclic aromatic amine DNA adduct N-(deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-f]quinoline in livers of rats using capillary liquid chromatography/microelectrospray mass spectrometry: a dose-response study. Soglia, J.R., Turesky, R.J., Paehler, A., Vouros, P. Anal. Chem. (2001) [Pubmed]
  36. Metabolic activation and deactivation of arylamine carcinogens by recombinant human NAT1 and polymorphic NAT2 acetyltransferases. Hein, D.W., Doll, M.A., Rustan, T.D., Gray, K., Feng, Y., Ferguson, R.J., Grant, D.M. Carcinogenesis (1993) [Pubmed]
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