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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

CCRIS 2823     N-(4- phenylphenyl)hydroxylamine

Synonyms: AG-G-59763, CHEBI:16580, AC1Q7DJP, KB-58305, LS-77377, ...
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Disease relevance of N-Hydroxy-4-aminobiphenyl


High impact information on N-Hydroxy-4-aminobiphenyl


Biological context of N-Hydroxy-4-aminobiphenyl


Anatomical context of N-Hydroxy-4-aminobiphenyl

  • Using this method, we identified N-(deoxyguanosin-3',5'-bisphospho-8-yl)-4-aminobiphenyl (pdGp-ABP) as a major adduct and N-(deoxyadenosin-3',5'-bisphospho-8-yl)-4-aminobiphenyl (pdAp-ABP) as a minor adduct in an immortalized non-tumorigenic cell line of HUC following exposure to N-hydroxy-4-aminobiphenyl (N-OH-ABP) [11].
  • Sulphation of the genotoxic compounds N-hydroxy-4-aminobiphenyl (N-OH-4ABP) and N-hydroxy-4-acetylaminobiphenyl (N-OH-4AABP) was determined in cytosolic preparations of human foetal, neonatal and adult liver and foetal and neonatal adrenal gland [12].
  • 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 [13].
  • 3. After i.p. injection of 10 mg/kg 14C-ABP to rats, ferrihaemoglobin (HbFe3+) concn increased to 60% in 2 h, accompanied by accumulation of 14C activity in erythrocytes, indicating that the active metabolite, N-hydroxy-4-aminobiphenyl (N-hydroxy-ABP) had oxidized haemoglobin-Fe2+ (HbFe2+) and was bound to the erythrocyte [14].

Gene context of N-Hydroxy-4-aminobiphenyl


  1. Effects of partial hepatectomy and dietary phenobarbital on liver and mammary tumorigenesis by two N-hydroxy-N-acylaminobiphenyls in female CD rats. Shirai, T., Lee, M.S., Wang, C.Y., King, C.M. Cancer Res. (1981) [Pubmed]
  2. N-hydroxy-4-aminobiphenyl-DNA binding in human p53 gene: sequence preference and the effect of C5 cytosine methylation. Feng, Z., Hu, W., Rom, W.N., Beland, F.A., Tang, M.S. Biochemistry (2002) [Pubmed]
  3. Development of sarcomas in heterotopically transplanted rat urinary bladder unit exposed to glucuronic acid conjugate of N-hydroxy-4-aminobiphenyl. Hirao, Y., Miyata, Y., Hearn, W.L., Radomski, J.L., Oyasu, R. Cancer Lett. (1981) [Pubmed]
  4. Mutagenicities of N-acyl-N-arylhydroxylamines for Salmonella. Wang, C.Y., Linsmaier-Bednar, E.M., Lee, M.S., King, C.M. Chem. Biol. Interact. (1988) [Pubmed]
  5. 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]
  6. 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]
  7. Metabolic activation of N-hydroxy-4-acetylaminobiphenyl by cultured human breast epithelial cell line MCF 10A. Swaminathan, S., Frederickson, S.M., Hatcher, J.F. Carcinogenesis (1994) [Pubmed]
  8. 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]
  9. Preparation and characterization of antibodies against 3,2'-dimethyl-4-aminobiphenyl-modified DNA. Tada, M., Aoki, H., Kojima, M., Morita, T., Shirai, T., Yamada, H., Ito, N. Carcinogenesis (1989) [Pubmed]
  10. Acetyl transferase-mediated metabolic activation of N-hydroxy-4-aminobiphenyl by human uroepithelial cells. Frederickson, S.M., Hatcher, J.F., Reznikoff, C.A., Swaminathan, S. Carcinogenesis (1992) [Pubmed]
  11. Detection of deoxyadenosine-4-aminobiphenyl adduct in DNA of human uroepithelial cells treated with N-hydroxy-4-aminobiphenyl following nuclease P1 enrichment and 32P-postlabeling analysis. Hatcher, J.F., Swaminathan, S. Carcinogenesis (1995) [Pubmed]
  12. Sulphation of N-hydroxy-4-aminobiphenyl and N-hydroxy-4-acetylaminobiphenyl by human foetal and neonatal sulphotransferase. Gilissen, R.A., Hume, R., Meerman, J.H., Coughtrie, M.W. Biochem. Pharmacol. (1994) [Pubmed]
  13. 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]
  14. The metabolism of 4-aminobiphenyl in rat. I. Reaction of N-hydroxy-4-aminobiphenyl with rat blood in vivo. Karreth, S., Lenk, W. Xenobiotica (1991) [Pubmed]
  15. 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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