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Chemical Compound Review

Xenylamin     4-phenylaniline

Synonyms: Xenylamine, Aminobiphenyl, Biphenylamine, p-Xenylamine, CCRIS 26, ...
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Disease relevance of CCRIS 26


High impact information on CCRIS 26


Chemical compound and disease context of CCRIS 26


Biological context of CCRIS 26

  • Adduct detection by acylation with [35S]methionine: analysis of DNA adducts of 4-aminobiphenyl [13].
  • 32P-postlabeling assay in mice of transplacental DNA damage induced by the environmental carcinogens safrole, 4-aminobiphenyl, and benzo(a)pyrene [14].
  • Frequency of urination and its effects on metabolism, pharmacokinetics, blood hemoglobin adduct formation, and liver and urinary bladder DNA adduct levels in beagle dogs given the carcinogen 4-aminobiphenyl [15].
  • The demonstration that both the genetically determined slow acetylator phenotype and tobacco smoking are independently associated with levels of the carcinogen 4-aminobiphenyl in adducted hemoglobin suggests a single mechanism to explain the contribution of genetic susceptibility and environmental exposure in bladder carcinogenesis [16].
  • A sensitive 32P-postlabeling method enabled us to study the binding of the environmental carcinogens safrole (600 mumol/kg p.o.), 4-aminobiphenyl (800 mumol/kg), and benzo(a)pyrene (200 mumol/kg) to the DNA of various maternal and fetal tissues after administration of test carcinogens to pregnant ICR mice on day 18 of gestation [14].

Anatomical context of CCRIS 26


Associations of CCRIS 26 with other chemical compounds


Gene context of CCRIS 26


Analytical, diagnostic and therapeutic context of CCRIS 26


  1. Assay for mutagenicity of bile in Sprague-Dawley rats treated subcutaneously with intestinal carcinogens. Moriya, M., Ohta, T., Sugiyama, F., Miyazawa, T., Shirasu, Y. J. Natl. Cancer Inst. (1979) [Pubmed]
  2. Measurement of 4-aminobiphenyl-hemoglobin adducts in lung cancer cases and controls. Weston, A., Caporaso, N.E., Taghizadeh, K., Hoover, R.N., Tannenbaum, S.R., Skipper, P.L., Resau, J.H., Trump, B.F., Harris, C.C. Cancer Res. (1991) [Pubmed]
  3. Specificity of mutagenesis by 4-aminobiphenyl. A possible role for N-(deoxyadenosin-8-yl)-4-aminobiphenyl as a premutational lesion. Lasko, D.D., Harvey, S.C., Malaikal, S.B., Kadlubar, F.F., Essigmann, J.M. J. Biol. Chem. (1988) [Pubmed]
  4. 4-Aminobiphenyl and DNA Reactivity: Case Study Within the Context of the 2006 IPCS Human Relevance Framework for Analysis of a Cancer Mode of Action for Humans. Cohen, S.M., Boobis, A.R., Bette Meek, M.E., Preston, R.J., McGregor, D.B. Crit. Rev. Toxicol. (2006) [Pubmed]
  5. Role of TP53 in repair of N-(deoxyguanosin-8-yl)-4-aminobiphenyl adducts in human transitional cell carcinoma of the urinary bladder. Torino, J.L., Burger, M.S., Reznikoff, C.A., Swaminathan, S. Carcinogenesis (2001) [Pubmed]
  6. Acetylator phenotype, aminobiphenyl-hemoglobin adduct levels, and bladder cancer risk in white, black, and Asian men in Los Angeles, California. Yu, M.C., Skipper, P.L., Taghizadeh, K., Tannenbaum, S.R., Chan, K.K., Henderson, B.E., Ross, R.K. J. Natl. Cancer Inst. (1994) [Pubmed]
  7. 4-Aminobiphenyl hemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. Coghlin, J., Gann, P.H., Hammond, S.K., Skipper, P.L., Taghizadeh, K., Paul, M., Tannenbaum, S.R. J. Natl. Cancer Inst. (1991) [Pubmed]
  8. Cocarcinogenic interaction between D,L-tryptophan and 4-aminobiphenyl or 2-naphthylamine in dogs. Radomski, J.L., Radomski, T., MacDonald, W.E. J. Natl. Cancer Inst. (1977) [Pubmed]
  9. A probe for the mutagenic activity of the carcinogen 4-aminobiphenyl: synthesis and characterization of an M13mp10 genome containing the major carcinogen-DNA adduct at a unique site. Lasko, D.D., Basu, A.K., Kadlubar, F.F., Evans, F.E., Lay, J.O., Essigmann, J.M. Biochemistry (1987) [Pubmed]
  10. Involvement of nitroreductase and O-acetyltransferase on the mutagenicity of plant-activated benzidine and 4-aminobiphenyl. Ju, Y.H., Plewa, M.J. Environ. Mol. Mutagen. (1997) [Pubmed]
  11. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. Part II: alkylation far away from the amino function. Glende, C., Klein, M., Schmitt, H., Erdinger, L., Boche, G. Mutat. Res. (2002) [Pubmed]
  12. Human and Escherichia coli beta-glucuronidase hydrolysis of glucuronide conjugates of benzidine and 4-aminobiphenyl, and their hydroxy metabolites. Zenser, T.V., Lakshmi, V.M., Davis, B.B. Drug Metab. Dispos. (1999) [Pubmed]
  13. Adduct detection by acylation with [35S]methionine: analysis of DNA adducts of 4-aminobiphenyl. Sheabar, F.Z., Morningstar, M.L., Wogan, G.N. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  14. 32P-postlabeling assay in mice of transplacental DNA damage induced by the environmental carcinogens safrole, 4-aminobiphenyl, and benzo(a)pyrene. Lu, L.J., Disher, R.M., Reddy, M.V., Randerath, K. Cancer Res. (1986) [Pubmed]
  15. Frequency of urination and its effects on metabolism, pharmacokinetics, blood hemoglobin adduct formation, and liver and urinary bladder DNA adduct levels in beagle dogs given the carcinogen 4-aminobiphenyl. Kadlubar, F.F., Dooley, K.L., Teitel, C.H., Roberts, D.W., Benson, R.W., Butler, M.A., Bailey, J.R., Young, J.F., Skipper, P.W., Tannenbaum, S.R. Cancer Res. (1991) [Pubmed]
  16. Acetylation phenotype, carcinogen-hemoglobin adducts, and cigarette smoking. Vineis, P., Caporaso, N., Tannenbaum, S.R., Skipper, P.L., Glogowski, J., Bartsch, H., Coda, M., Talaska, G., Kadlubar, F. Cancer Res. (1990) [Pubmed]
  17. 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]
  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. Inhibition of the mutagenicity of aromatic amines by the plant flavonoid (+)-catechin. Steele, C.M., Lalies, M., Ioannides, C. Cancer Res. (1985) [Pubmed]
  20. Bovine bladder mucosa microsomal cytochrome P-450 and 4-aminobiphenyl N-hydroxylase activity. Poupko, J.M., Radomski, J.L., Hearn, W.L. Cancer Res. (1981) [Pubmed]
  21. Modulation of biomarkers by chemopreventive agents in smoke-exposed rats. Izzotti, A., Balansky, R.M., Dagostini, F., Bennicelli, C., Myers, S.R., Grubbs, C.J., Lubet, R.A., Kelloff, G.J., De Flora, S. Cancer Res. (2001) [Pubmed]
  22. Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4'-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Butler, M.A., Guengerich, F.P., Kadlubar, F.F. Cancer Res. (1989) [Pubmed]
  23. NMR-based Model Reveals the Structural Determinants of Mammalian Arylamine N-Acetyltransferase Substrate Specificity. Zhang, N., Liu, L., Liu, F., Wagner, C.R., Hanna, P.E., Walters, K.J. J. Mol. Biol. (2006) [Pubmed]
  24. Quantification of N-(Deoxyguanosin-8-yl)-4-aminobiphenyl Adducts in Human Lymphoblastoid TK6 Cells Dosed with N-hydroxy-4-acetylaminobiphenyl and Their Relationship to Mutation, Toxicity, and Gene Expression Profiling. Ricicki, E.M., Luo, W., Fan, W., Zhao, L.P., Zarbl, H., Vouros, P. Anal. Chem. (2006) [Pubmed]
  25. Carotenoids/vitamin C and smoking-related bladder cancer. Castelao, J.E., Yuan, J.M., Gago-Dominguez, M., Skipper, P.L., Tannenbaum, S.R., Chan, K.K., Watson, M.A., Bell, D.A., Coetzee, G.A., Ross, R.K., Yu, M.C. Int. J. Cancer (2004) [Pubmed]
  26. Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucuronides. Ciotti, M., Lakshmi, V.M., Basu, N., Davis, B.B., Owens, I.S., Zenser, T.V. Carcinogenesis (1999) [Pubmed]
  27. 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]
  28. CYP1A2 is not the primary enzyme responsible for 4-aminobiphenyl-induced hepatocarcinogenesis in mice. Kimura, S., Kawabe, M., Ward, J.M., Morishima, H., Kadlubar, F.F., Hammons, G.J., Fernandez-Salguero, P., Gonzalez, F.J. Carcinogenesis (1999) [Pubmed]
  29. Human UDP-glucuronosyltransferase 1A5: identification, expression, and activity. Finel, M., Li, X., Gardner-Stephen, D., Bratton, S., Mackenzie, P.I., Radominska-Pandya, A. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  30. Effect of carcinogenic components of cigarette smoke on in vivo production of murine interferon. Sonnenfeld, G., Hudgens, R.W. Cancer Res. (1983) [Pubmed]
  31. Detection and characterization of carcinogen-DNA adducts in exfoliated urothelial cells from 4-aminobiphenyl-treated dogs by 32P-postlabelling and subsequent thin-layer and high-pressure liquid chromatography. Talaska, G., Dooley, K.L., Kadlubar, F.F. Carcinogenesis (1990) [Pubmed]
  32. Complex frameshift mutations mediated by plasmid pKM101: mutational mechanisms deduced from 4-aminobiphenyl-induced mutation spectra in Salmonella. Levine, J.G., Schaaper, R.M., DeMarini, D.M. Genetics (1994) [Pubmed]
  33. Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites. pH stability and synthesis by human and dog liver. Babu, S.R., Lakshmi, V.M., Huang, G.P., Zenser, T.V., Davis, B.B. Biochem. Pharmacol. (1996) [Pubmed]
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