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Chemical Compound Review

CCRIS 1212     2-nitroso-9H-fluorene

Synonyms: AG-E-75791, HSDB 2112, LS-69284, CTK1A3347, AKOS006273447, ...
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Disease relevance of CCRIS 1212

  • The use of a nitroreductase deficient strain of Salmonella, coupled with t.l.c. analysis, however, also indicates the presence of a minor component whose mutagenic and t.l.c. properties are identical with 2-nitrosofluorene [1].

High impact information on CCRIS 1212


Biological context of CCRIS 1212


Anatomical context of CCRIS 1212

  • N-Hydroxy-2-FBS applied directly to the mammary gland was not carcinogenic and 2-nitrosofluorene, the product of the spontaneous decomposition of N-hydroxy-2-FBS, exhibited only weak carcinogenicity upon local application [7].
  • The data are consistent with the suggestion that NF elicits defects in axial rotation primarily via its effects on the visceral yolk sac and demonstrate the capacity of this technique to provide insights into mechanistic aspects of chemical dysmorphogenesis [8].
  • Free radicals and carcinogenesis. Some properties of the nitroxyl free radicals produced by covalent binding of 2-nitrosofluorene to unsaturated lipids of membranes [9].
  • We have demonstrated that incubation of rat liver microsomes with N-hydroxy-2-acetylaminofluorene (N-OH-AAF) leads to formation of a 2-nitrosofluorene-membrane lipid adduct [10].

Associations of CCRIS 1212 with other chemical compounds


Gene context of CCRIS 1212

  • Treatment of NAT1 with 2-nitrosofluorene resulted in a modification (+195 Da) that was identical in mass to that obtained with N-OH-AAF-inactivated enzyme [15].


  1. Phototransformation of 2-aminofluorene into N-oxidized mutagens. Okinaka, R.T., Nickols, J.W., Whaley, T.W., Strniste, G.F. Carcinogenesis (1984) [Pubmed]
  2. The cytochrome P-450 monooxygenase system of rabbit bladder mucosa: enzyme components and isozyme 5-dependent metabolism of 2-aminofluorene. Vanderslice, R.R., Boyd, J.A., Eling, T.E., Philpot, R.M. Cancer Res. (1985) [Pubmed]
  3. Enhancement of N-hydroxy-2-aminofluorene bacterial mutagenicity by the soluble protein fraction from rat liver and partial purification of the enhancement activity. Saccone, G.T., DasGupta, B.R., Pariza, M.W. Cancer Res. (1981) [Pubmed]
  4. Horseradish peroxidase/hydrogen peroxide-catalyzed oxidation of the carcinogen N-hydroxy-N-acetyl-2-aminofluorene as effected by cyanide and ascorbate. Floyd, R.A., Soong, L.M., Culver, P.L. Cancer Res. (1976) [Pubmed]
  5. Lipid hydroperoxide activation of N-hydroxy-N-acetylaminofluorene via a free radical route. Floyd, R.A., Soong, L.M., Walker, R.N., Stuart, M. Cancer Res. (1976) [Pubmed]
  6. Mitochondrial permeability transition is altered in early stages of carcinogenesis of 2-acetylaminofluorene. Klöhn, P.C., Bitsch, A., Neumann, H.G. Carcinogenesis (1998) [Pubmed]
  7. N-hydroxy-2-fluorenylacetamide, an active intermediate of the mammary carcinogen N-hydroxy-2-fluorenylbenzenesulfonamide. Malejka-Giganti, D., Gutmann, H.R. Proc. Soc. Exp. Biol. Med. (1975) [Pubmed]
  8. Microinjection of cultured rat embryos: a new technique for studies in chemical dysmorphogenesis. Stark, K.L., Juchau, M.R. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  9. Free radicals and carcinogenesis. Some properties of the nitroxyl free radicals produced by covalent binding of 2-nitrosofluorene to unsaturated lipids of membranes. Floyd, R.A., Soong, L.M., Stuart, M.A., Reigh, D.L. Arch. Biochem. Biophys. (1978) [Pubmed]
  10. The deacetylation of N-hydroxy-2-acetylaminofluorene by rat liver microsomes and carboxyl esterase. Steward, J.E., Floyd, R.A. Cancer Biochem. Biophys. (1980) [Pubmed]
  11. 2-Nitrosofluorene and N-hydroxy-2-aminofluorene react with the ubiquinone-reduction center (center N) of the mitochondrial cytochrome bc1 complex. Klöhn, P.C., Brandt, U., Neumann, H.G. FEBS Lett. (1996) [Pubmed]
  12. Regulation of intracellular glutathione in rat embryos and visceral yolk sacs and its effect on 2-nitrosofluorene-induced malformations in the whole embryo culture system. Harris, C., Namkung, M.J., Juchau, M.R. Toxicol. Appl. Pharmacol. (1987) [Pubmed]
  13. Impairment of respiration and oxidative phosphorylation by redox cyclers 2-nitrosofluorene and menadione. Klöhn, P.C., Neumann, H.G. Chem. Biol. Interact. (1997) [Pubmed]
  14. Mutagenic, cytotoxic, and teratogenic effects of 2-acetylaminofluorene and reactive metabolites in vitro. Faustman-Watts, E.M., Yang, H.Y., Namkung, M.J., Greenaway, J.C., Fantel, A.G., Juchau, M.R. Teratog., Carcinog. Mutagen. (1984) [Pubmed]
  15. Mass spectrometric investigation of the mechanism of inactivation of hamster arylamine N-acetyltransferase 1 by N-hydroxy-2-acetylaminofluorene. Guo, Z., Wagner, C.R., Hanna, P.E. Chem. Res. Toxicol. (2004) [Pubmed]
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