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Chemical Compound Review

O-AMINOPHENL     2-aminophenol

Synonyms: O-AMINOPHENOL, Questiomycin B, Fouramine OP, Benzofur GG, Pelagol 3GA, ...
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Disease relevance of 2AF


High impact information on 2AF


Chemical compound and disease context of 2AF


Biological context of 2AF

  • These data are consistent with the existence of more than one binding site for o-aminophenol on UDP-glucuronyltransferase [12].
  • 7. From this and from evidence previously presented we suggest that glucocorticoids, which are known to increase in rat foetuses between days 17 and 20 of gestation, trigger the normal development in utero of hepatic transferase activity towards o-aminophenol which occurs at that time [13].
  • The predicted amino acid sequences of these proteins are highly homologous to those of the corresponding proteins involved in the metabolism of 2-aminophenol (e.g., AmnCDEFGH in Pseudomonas sp. strain AP-3) [14].
  • Rapid release of ammonia from 2-aminophenol transformation indicated that hydrolysis of the imine intermediate was the dominant reaction [15].
  • On the other hand, the genes nbzC, nbzD, and nbzE, involved in the ring cleavage pathway of 2-aminophenol, are localized on the 6.6-kb SnaBI-SmaI fragment of pNB1 and clustered in the order nbzC-nbzD-nbzE as an operon [16].

Anatomical context of 2AF


Associations of 2AF with other chemical compounds


Gene context of 2AF


Analytical, diagnostic and therapeutic context of 2AF

  • The final product of o-aminophenol was identified as 2-aminophenoxazine-3-one, by using spectrophotometry and HPLC [25].


  1. Novel genes encoding 2-aminophenol 1,6-dioxygenase from Pseudomonas species AP-3 growing on 2-aminophenol and catalytic properties of the purified enzyme. Takenaka, S., Murakami, S., Shinke, R., Hatakeyama, K., Yukawa, H., Aoki, K. J. Biol. Chem. (1997) [Pubmed]
  2. Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway). He, Z., Spain, J.C. Arch. Microbiol. (1999) [Pubmed]
  3. A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1: purification, properties, genetic cloning and expression in Escherichia coli. Wu, J.F., Sun, C.W., Jiang, C.Y., Liu, Z.P., Liu, S.J. Arch. Microbiol. (2005) [Pubmed]
  4. A novel meta-cleavage dioxygenase that cleaves a carboxyl-group-substituted 2-aminophenol. Purification and characterization of 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. strain 10d. Takenaka, S., Asami, T., Orii, C., Murakami, S., Aoki, K. Eur. J. Biochem. (2002) [Pubmed]
  5. Proliferation of endoplasmic reticulum with its enzyme, UDP-glucuronyltransferase, in chick embryo liver during culture. Effects of phenobarbital. Banjo, A.O., Nemeth, A.M. J. Cell Biol. (1976) [Pubmed]
  6. Contribution of aniline metabolites to aniline-induced methemoglobinemia. Harrison, J.H., Jollow, D.J. Mol. Pharmacol. (1987) [Pubmed]
  7. Bioelectrochemical monitoring of phenols and aromatic amines in flow injection using novel plant peroxidases. Munteanu, F.D., Lindgren, A., Emnéus, J., Gorton, L., Ruzgas, T., Csŏregi, E., Ciucu, A., van Huystee, R.B., Gazaryan, I.G., Lagrimini, L.M. Anal. Chem. (1998) [Pubmed]
  8. Synthesis and topical antiinflammatory and antiallergic activities of antioxidant o-aminophenol derivatives. Sugiyama, N., Akahoshi, F., Kuwahara, S., Kajii, M., Sakaue, Y., Yakumaru, H., Sugiura, M., Fukaya, C. J. Med. Chem. (1994) [Pubmed]
  9. Identification of increased amounts of UDP-glucuronyltransferase protein in phenobarbital-treated chick-embryo liver cells. Burchell, B., Pratt, G.J., Duffy, I., West, L. Biochem. J. (1983) [Pubmed]
  10. Sequence analysis and initial characterization of two isozymes of hydroxylaminobenzene mutase from Pseudomonas pseudoalcaligenes JS45. Davis, J.K., Paoli, G.C., He, Z., Nadeau, L.J., Somerville, C.C., Spain, J.C. Appl. Environ. Microbiol. (2000) [Pubmed]
  11. Genetic and biochemical comparison of 2-aminophenol 1,6-dioxygenase of Pseudomonas pseudoalcaligenes JS45 to meta-cleavage dioxygenases: divergent evolution of 2-aminophenol meta-cleavage pathway. Davis, J.K., He, Z., Somerville, C.C., Spain, J.C. Arch. Microbiol. (1999) [Pubmed]
  12. Possible multiple binding sites for o-aminophenol on uridine diphosphate glucuronyltransferase. Howland, R.D., Bohm, L.D. Biochem. J. (1977) [Pubmed]
  13. Regulation of onset of development of UDP-glucuronosyltransferase activity towards o-aminophenol by glucocorticoids in late-foetal rat liver in utero. Wishart, G.J., Dutton, G.J. Biochem. J. (1977) [Pubmed]
  14. Prokaryotic homologs of the eukaryotic 3-hydroxyanthranilate 3,4-dioxygenase and 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase in the 2-nitrobenzoate degradation pathway of Pseudomonas fluorescens strain KU-7. Muraki, T., Taki, M., Hasegawa, Y., Iwaki, H., Lau, P.C. Appl. Environ. Microbiol. (2003) [Pubmed]
  15. Biotransformation of hydroxylaminobenzene and aminophenol by Pseudomonas putida 2NP8 cells grown in the presence of 3-nitrophenol. Zhao, J.S., Singh, A., Huang, X.D., Ward, O.P. Appl. Environ. Microbiol. (2000) [Pubmed]
  16. Identification and characterization of the nitrobenzene catabolic plasmids pNB1 and pNB2 in Pseudomonas putida HS12. Park, H.S., Kim, H.S. J. Bacteriol. (2000) [Pubmed]
  17. Light microscopic localization of glycosyltransferase activities in cells and tissues. Benau, D.A., Schumacher, W.G., McGuire, E.J., Fitzpatrick-McElligott, S., Storey, B.T., Roth, S. J. Histochem. Cytochem. (1990) [Pubmed]
  18. Biotransformation of pentachlorophenol, aniline and biphenyl in isolated rainbow trout (Oncorhynchus mykiss) hepatocytes: comparison with in vivo metabolism. Cravedi, J.P., Lafuente, A., Baradat, M., Hillenweck, A., Perdu-Durand, E. Xenobiotica (1999) [Pubmed]
  19. The effect of erythrocytes and hemoglobin on sister chromatid exchange induction in cultured human lymphocytes exposed to aniline HCI. Wilmer, J.L., Erexson, G.L., Kligerman, A.D. Basic Life Sci. (1984) [Pubmed]
  20. 2-aminophenol 1,6-dioxygenase: a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS45. Lendenmann, U., Spain, J.C. J. Bacteriol. (1996) [Pubmed]
  21. Effects of proton pump inhibitors on thyroid hormone metabolism in rats: a comparison of UDP-glucuronyltransferase induction. Masubuchi, N., Hakusui, H., Okazaki, O. Biochem. Pharmacol. (1997) [Pubmed]
  22. Determination of aniline and metabolites produced in vitro by liquid chromatography/electrochemistry. Radzik, D.M., Kissinger, P.T. Anal. Biochem. (1984) [Pubmed]
  23. Aniline and its metabolites generate free radicals in yeast. Brennan, R.J., Schiestl, R.H. Mutagenesis (1997) [Pubmed]
  24. Determination of aminophenol isomers by high-speed liquid chromatography. Sakurai, H., Ogawa, S. Journal of chromatographic science. (1976) [Pubmed]
  25. Mechanism of o-aminophenol metabolism in human erythrocytes. Tomoda, A., Yamaguchi, J., Kojima, H., Amemiya, H., Yoneyama, Y. FEBS Lett. (1986) [Pubmed]
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