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Chemical Compound Review

CCRIS 22     anthracen-2-amine

Synonyms: CHEMBL83154, A38800_ALDRICH, AG-G-23267, ACMC-209mrd, CHEBI:34260, ...
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Disease relevance of anthracen-2-amine


High impact information on anthracen-2-amine


Chemical compound and disease context of anthracen-2-amine

  • Anti-mutagenicity was determined in the Salmonella typhimurium assay by measuring the effects of the test compounds on bacterial mutagenesis induced by methyl-nitrosourea (MNU), methyl-n-nitro-N-nitrosoguanidine (MNNG), benzo[a]pyrene (BaP) or 2-aminoanthracene (2-AA) [8].
  • In this study, S9, cytosolic fractions (CF), and microsomal fractions (MF) prepared from unexposed clams and clams exposed to model pollutants were used to activate 2-aminoanthracene (2-AA) and 2-acetylaminofluorene (AAF) to mutagens in Salmonella typhimurium strain BA149, which overexpresses O-acetyltransferase [9].
  • In the first group of experiments the effects of increasing the concentration of S9 from untreated and 3-methylcholanthrene (MC)- or Aroclor 1254 (AC)-pretreated toadfish and Sprague-Dawley rats on the mutagenicities of different concentrations of 2-aminoanthracene (2AA) and benzo[a]pyrene (BAP) were examined in Salmonella (TA98) plate assays [10].
  • Four different indirect mutagens, 2-aminoanthracene, benzo[a]pyrene, 7,12-dimetylbenz[a]anthracene and cyclophosphamide, were used with the liver cells as metabolizing system in the preincubation assay with Salmonella typhimurium TA100 [11].
  • 6-Aminochrysene and 2-aminoanthracene were activated to metabolites which were mutagenic to Salmonella typhimurium TA98 by hepatocytes or hepatic 9000 X g supernatants (S9s) from control or xenobiotic-treated rats [12].

Biological context of anthracen-2-amine


Anatomical context of anthracen-2-amine


Associations of anthracen-2-amine with other chemical compounds


Gene context of anthracen-2-amine

  • Mutagenicity of 2-aminoanthracene in strain DJ4309 is higher than can be obtained by rat liver homogenate 9000g supernatant (S9) activation in the parent strain lacking the P450 expression vector [25].
  • The rabbit CYP4B1 converts this prodrug and other furane analogs and aromatic amines, such as 2-aminoanthracene, to highly toxic alkylating metabolites, whereas the human isoenzyme exhibits only minimal enzymatic activity [26].
  • Mutagenicity of precarcinogens known to be bioactivated by CYP1A2, namely 2-aminoanthracene (2-AA), aflatoxin B1 (AFB1) and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), could be detected [27].
  • The well-known mutagens 2-aminoanthracene and MelQ increased the revertant colonies of E. coli WP2 uvrA expressing human P450 1A2 without an exogenous rat hepatic post-mitochondrial supernatant (S9 fraction) in a dose-dependent manner [28].
  • 2-aminoanthracene as an analytical tool with the acetylation reaction catalyzed by arylamine N-acetyltransferase [29].

Analytical, diagnostic and therapeutic context of anthracen-2-amine


  1. Effect of human colonic microsomes and cell-free extracts of Bacteroides fragilis on the mutagenicity of 2-aminoanthracene. Tasich, M., Piper, D.W. Gastroenterology (1983) [Pubmed]
  2. Effect of microsomal cytochrome P-450 isozyme induction on the mutagenic activation of 2-aminoanthracene. Norman, R.L., Muller-Eberhard, U., Johnson, E.F. Cancer Res. (1982) [Pubmed]
  3. Evaluation of the Escherichia coli K12 inductest for detection of potential chemical carcinogens. Mamber, S.W., Bryson, V., Katz, S.E. Mutat. Res. (1984) [Pubmed]
  4. Sensitivity of carcinogen-treated DNA to inactivation by ultraviolet radiation. Larcom, L.L., Wood, D.C. Mutat. Res. (1985) [Pubmed]
  5. Differential cytotoxicity and bystander effect of the rabbit cytochrome P450 4B1 enzyme gene by two different prodrugs: implications for pharmacogene therapy. Frank, S., Steffens, S., Fischer, U., Tlolko, A., Rainov, N.G., Kramm, C.M. Cancer Gene Ther. (2002) [Pubmed]
  6. Inhibition of human cytochrome P450-catalyzed oxidations of xenobiotics and procarcinogens by synthetic organoselenium compounds. Shimada, T., El-Bayoumy, K., Upadhyaya, P., Sutter, T.R., Guengerich, F.P., Yamazaki, H. Cancer Res. (1997) [Pubmed]
  7. New prodrug activation gene therapy for cancer using cytochrome P450 4B1 and 2-aminoanthracene/4-ipomeanol. Rainov, N.G., Dobberstein, K.U., Sena-Esteves, M., Herrlinger, U., Kramm, C.M., Philpot, R.M., Hilton, J., Chiocca, E.A., Breakefield, X.O. Hum. Gene Ther. (1998) [Pubmed]
  8. Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol. Birt, D.F., Walker, B., Tibbels, M.G., Bresnick, E. Carcinogenesis (1986) [Pubmed]
  9. Mutagenic activation of arylamines by subcellular fractions of Chamaelea gallina clams exposed to environmental pollutants. Rodríguez-Ortega, M.J., Rodríguez-Ariza, A., Amezcua, O., López-Barea, J. Environ. Mol. Mutagen. (2003) [Pubmed]
  10. Activation and detoxication of promutagens by toadfish (Opsanus tau) hepatic postmitochondrial fractions in the Salmonella assay. Milling, D.M., Maddock, M.B. Mutat. Res. (1986) [Pubmed]
  11. Cryopreserved and hypothermically stored rat liver parenchymal cells as metabolizing system in the Salmonella mutagenicity assay. Diener, B., Oesch, F. Mutat. Res. (1995) [Pubmed]
  12. Preferential activation of 6-aminochrysene and 2-aminoanthracene to mutagenic moieties by different forms of cytochrome P450 in hepatic 9000 X g supernatants from the rat. Lubet, R.A., McKinney, C.E., Cameron, J.W., Guengerich, F.P., Nims, R.W. Mutat. Res. (1989) [Pubmed]
  13. Distribution, retention, and fate of 2-aminoanthracene in rats after inhalation. Mitchell, C.E., Henderson, R.F., McClellan, R.O. Toxicol. Appl. Pharmacol. (1984) [Pubmed]
  14. SOS-inducing activity of chemical carcinogens and mutagens in Salmonella typhimurium TA1535/pSK1002: examination with 151 chemicals. Nakamura, S.I., Oda, Y., Shimada, T., Oki, I., Sugimoto, K. Mutat. Res. (1987) [Pubmed]
  15. Studies on the potential in vivo induction of sister-chromatid exchanges in rat bone marrow by resorcinol. Bracher, M., Swistak, J., Noser, F. Mutat. Res. (1981) [Pubmed]
  16. Genotoxicity assessment of aromatic amines and amides in genetically engineered V79 cells. Rodrigues, A.S., Silva, I.D., Caria, M.H., Laires, A., Chaveca, T., Glatt, H.R., Rueff, J. Mutat. Res. (1994) [Pubmed]
  17. Aflatoxin B1, 2-aminoanthracene, and 7,12-dimethylbenz[a]anthracene-induced frameshift mutations in human APRT. Zhu, Y., Bye, S., Stambrook, P.J., Tischfield, J.A. Environ. Mol. Mutagen. (1995) [Pubmed]
  18. Metabolism of 2-aminoanthracene by BALB/c and C57BL mammary epithelium in vitro. Silva, M.H., Petrakis, N.L., Musker, W.K., Talcott, R.E. Carcinogenesis (1985) [Pubmed]
  19. Metabolic activation of environmental carcinogens and mutagens by human liver microsomes. Role of cytochrome P-450 homologous to a 3-methylcholanthrene-inducible isozyme in rat liver. Shimada, T., Okuda, Y. Biochem. Pharmacol. (1988) [Pubmed]
  20. Studies on microsomal cytochrome P-450, monooxygenases and epoxide hydrolase in cultured keratinocytes and intact epidermis from BALB/C mice. Bickers, D.R., Marcelo, C.L., Dutta-Choudhury, T., Mukhtar, H. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  21. A green to blue fluorescence switch of protonated 2-aminoanthracene upon inclusion in cucurbit[7]uril. Wang, R., Yuan, L., Macartney, D.H. Chem. Commun. (Camb.) (2005) [Pubmed]
  22. Activation of mammalian carcinogens to bacterial mutagens by microsomal enzymes from a pelecypod mollusk, Mercenaria mercenaria. Anderson, R.S., Döös, J.E. Mutat. Res. (1983) [Pubmed]
  23. Characterization of the in vitro unscheduled DNA synthesis assay in primary lung cells of the rat. Whong, W.Z., Stewart, J.D., Ong, T. Mutat. Res. (1991) [Pubmed]
  24. Cytosolic activation of 2-aminoanthracene: implications in its use as diagnostic mutagen in the Ames test. Ayrton, A.D., Neville, S., Ioannides, C. Mutat. Res. (1992) [Pubmed]
  25. Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli. Josephy, P.D., Evans, D.H., Parikh, A., Guengerich, F.P. Chem. Res. Toxicol. (1998) [Pubmed]
  26. Rabbit cytochrome P450 4B1: A novel prodrug activating gene for pharmacogene therapy of hepatocellular carcinoma. Mohr, L., Rainov, N.G., Mohr, U.G., Wands, J.R. Cancer Gene Ther. (2000) [Pubmed]
  27. Expression of human cytochrome P450 1A2 in Escherichia coli: a system for biotransformation and genotoxicity studies of chemical carcinogens. Kranendonk, M., Mesquita, P., Laires, A., Vermeulen, N.P., Rueff, J. Mutagenesis (1998) [Pubmed]
  28. Expression of recombinant human cytochrome P450 1A2 in Escherichia coli bacterial mutagenicity tester strain. Chun, Y.J. Arch. Pharm. Res. (1998) [Pubmed]
  29. 2-aminoanthracene as an analytical tool with the acetylation reaction catalyzed by arylamine N-acetyltransferase. Servillo, L., Balestrieri, C., Boccellino, M., Balestrieri, M.L., Quagliuolo, L., Giovane, A. Anal. Biochem. (1999) [Pubmed]
  30. The effect of solvents upon the yield of revertants in the Salmonella/activation mutagenicity assay. Anderson, D., McGregor, D.B. Carcinogenesis (1980) [Pubmed]
  31. Separation and detection of 2-aminoanthracene and its metabolites by high-performance liquid chromatography. Shaikh, B., Hallmark, M.R., Hallmark, R.K., Manning, W.B., Pinnock, A., Kawalek, J.C. J. Chromatogr. (1980) [Pubmed]
  32. The effect of solvents on drug metabolism in vitro. Kawalek, J.C., Andrews, A.W. Drug Metab. Dispos. (1980) [Pubmed]
  33. Formation of mutagenic metabolites from benzo(a)pyrene and 2-aminoanthracene by the s-9 fraction from the liver of the Northern pike (Esox lucius): inducibility with 3-methylcholanthrene and correlation with benzo[a]pyrene monooxygenase activity. Balk, L., Depierre, J.W., Sundvall, A., Rannug, U. Chem. Biol. Interact. (1982) [Pubmed]
  34. New methods to use fish cytochrome P4501A to assess marine organic pollutants. Cousinou, M., Nilsen, B., López-Barea, J., Dorado, G. Sci. Total Environ. (2000) [Pubmed]
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