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Chemical Compound Review

pyrenylamine     pyren-1-amine

Synonyms: CCRIS 760, CHEMBL400756, ACMC-1BODO, A77903_ALDRICH, AG-E-10228, ...
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Disease relevance of NSC 11436


High impact information on NSC 11436


Biological context of NSC 11436


Anatomical context of NSC 11436


Associations of NSC 11436 with other chemical compounds


Gene context of NSC 11436

  • It was shown that the CBP bound the environmental carcinogen 1-nitropyrene, its reduced metabolite 1-aminopyrene and the ultimate carcinogenic metabolite of benzo[a]pyrene or (+)-r-7,t-8-dihydroxy-t-9,10-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene but not the smaller coplanar PCB molecule, 3,3',4,4'-tetrachlorobiphenyl [19].

Analytical, diagnostic and therapeutic context of NSC 11436

  • High-pressure liquid chromatography analysis showed that 1-NP was converted by S9 mix to several metabolites, including 1-aminopyrene (AP) [20].
  • The former metabolite was identified as 1-aminopyrene and the latter two metabolites as 1-acetylaminopyrene and 1-formylaminopyrene by comparing their mass and UV spectra, and their behaviors in HPLC and TLC, with those of authentic samples [21].
  • This study presents a sensitive and selective method for detection of Hb adducts after oral administration of a single dose 1-NP to rats, by measuring 1-aminopyrene (1-AP) after in vitro hydrolysis of the adducts [22].


  1. Metabolism of 1-nitropyrene and formation of DNA adducts in Salmonella typhimurium. Messier, F., Lu, C., Andrews, P., McCarry, B.E., Quilliam, M.A., McCalla, D.R. Carcinogenesis (1981) [Pubmed]
  2. Photochemical transformation and phototoxicity of 1-aminopyrene. Zeng, K., Hwang, H.M., Dong, S., Shi, X., Wilson, K., Green, J., Jiao, Y., Yu, H. Environ. Toxicol. Chem. (2004) [Pubmed]
  3. Ultraviolet radiation increases the toxicity of pyrene, 1-aminopyrene and 1-hydroxypyrene to human keratinocytes. Ekunwe, S.I., Hunter, R.D., Hwang, H.M. International journal of environmental research and public health [electronic resource]. (2005) [Pubmed]
  4. Comparative tumorigenicity of 1-nitropyrene, 1-nitrosopyrene, and 1-aminopyrene administered by gavage to Sprague-Dawley rats. el-Bayoumy, K., Rivenson, A., Johnson, B., DiBello, J., Little, P., Hecht, S.S. Cancer Res. (1988) [Pubmed]
  5. Induction of cytochrome P450 1B1 in lung, liver and kidney of rats exposed to diesel exhaust. Hatanaka, N., Yamazaki, H., Kizu, R., Hayakawa, K., Aoki, Y., Iwanari, M., Nakajima, M., Yokoi, T. Carcinogenesis (2001) [Pubmed]
  6. Thermodynamic and kinetic characterization of nitrogen-containing polycyclic aromatic hydrocarbons in reversed-phase liquid chromatography. McGuffin, V.L., Howerton, S.B., Li, X. Journal of chromatography. A. (2005) [Pubmed]
  7. Comparison of three different in vitro mutation assays used for the investigation of cytochrome P450-mediated mutagenicity of nitro-polycyclic aromatic hydrocarbons. Kappers, W.A., van Och, F.M., de Groene, E.M., Horbach, G.J. Mutat. Res. (2000) [Pubmed]
  8. Toxicity and DNA damage induced by 1-nitropyrene and its derivatives in Chinese hamster lung fibroblasts. Edwards, M.J., Parry, J.M., Batmanghelich, S., Smith, K. Mutat. Res. (1986) [Pubmed]
  9. Facile route for the synthesis of the iminosugar nucleoside (3R,4R)-1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol. Hassan, A.A., Jørgensen, P.T., Stein, P.C., Fattah, M.E., el-Gawad, I.I., Pedersen, E.B. Carbohydr. Res. (2004) [Pubmed]
  10. Metabolism of 1-nitropyrene in germ-free and conventional rats. Kinouchi, T., Morotomi, M., Mutai, M., Fifer, E.K., Beland, F.A., Ohnishi, Y. Jpn. J. Cancer Res. (1986) [Pubmed]
  11. Comparison of metabolic activation of carcinogens in human, rat, and hamster hepatocytes. Synder, S., Hsu, I.C., Trump, B.F. Mutat. Res. (1987) [Pubmed]
  12. Metabolism of 1-nitropyrene by cultured rabbit alveolar macrophages and respiratory tract tissues. King, L.C., Ball, L.M., Jackson, M., Inmon, J.P., Lewtas, J. Toxicol. Appl. Pharmacol. (1986) [Pubmed]
  13. The induction of DNA adducts in mammalian cells exposed to 1-nitropyrene and its nitro-reduced derivatives. Edwards, M.J., Batmanghelich, S., Edwards, S., Parry, J.M., Smith, K. Mutagenesis (1986) [Pubmed]
  14. Detection and characterization of a novel hepatic 8 S binding protein for benzo[a]pyrene distinct from the Ah receptor. Lesca, P., Peryt, B., Soues, S., Maurel, P., Cravedi, J.P. Arch. Biochem. Biophys. (1993) [Pubmed]
  15. Microsomal activation of selected polycyclic aromatic hydrocarbons and aromatic amines in Drosophila melanogaster. Nix, C.E., Brewen, B., Epler, J.L. Mutat. Res. (1981) [Pubmed]
  16. The stimulatory role of human cytochrome b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a new cell expression system to study cytochrome P450 mediated biotransformation. Duarte, M.P., Palma, B.B., Gilep, A.A., Laires, A., Oliveira, J.S., Usanov, S.A., Rueff, J., Kranendonk, M. Mutagenesis (2005) [Pubmed]
  17. Composite poly(methyl methacrylate-methacrylic acid-2-hydroxyethyl methacrylate) latex for immunoassay. The case of plasminogen. Miksa, B., Wilczynska, M., Cierniewski, C., Basinska, T., Slomkowski, S. Journal of biomaterials science. Polymer edition. (1995) [Pubmed]
  18. Association interaction and voltammetric determination of 1-aminopyrene and 1-hydroxypyrene at cyclodextrin and DNA based electrochemical sensors. Ferancová, A., Bucková, M., Korgová, E., Korbut, O., Gründler, P., Wärnmark, I., Stepán, R., Barek, J., Zima, J., Labuda, J. Bioelectrochemistry (Amsterdam, Netherlands) (2005) [Pubmed]
  19. The 4-5S carcinogen binding protein binds 1-aminopyrene, 1-nitropyrene and (+)-benzo[a]pyrenediolepoxide and is found in 12 tissues of the DBA/2J mouse. Zytkovicz, T.H. Toxicol. Lett. (1987) [Pubmed]
  20. Clastogenicity of 1-nitropyrene, dinitropyrenes, fluorene and mononitrofluorenes in cultured Chinese hamster cells. Matsuoka, A., Sofuni, T., Miyata, N., Ishidate, M. Mutat. Res. (1991) [Pubmed]
  21. Metabolism in vivo of 1-nitropyrene, an environmental pollutant, in fish. Kitamura, S., Tatsumi, K. Biol. Pharm. Bull. (1996) [Pubmed]
  22. Determination of hemoglobin adducts following oral administration of 1-nitropyrene to rats using gas chromatography-tandem mass spectrometry. van Bekkum, Y.M., Scheepers, P.T., van den Broek, P.H., Velders, D.D., Noordhoek, J., Bos, R.P. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]
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