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Chemical Compound Review

CHEMBL349860     1,6-dinitropyrene

Synonyms: ACMC-1AN8R, CCRIS 2212, D9288_SIGMA, BIDD:ER0474, CTK1D7517, ...
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Disease relevance of CCRIS 2212


High impact information on CCRIS 2212


Biological context of CCRIS 2212


Anatomical context of CCRIS 2212

  • These findings indicate that concentrations of 1,6-dinitropyrene that produce a dose-dependent induction of lung tumors also result in a dose-dependent formation of DNA adducts and induction of lymphocyte mutations but that the dose-response curves for DNA binding and mutations are different [15].
  • 1,6-Dinitropyrene and 1-nitropyrene induced unscheduled DNA synthesis in epithelial cells of in vitro cultured human bronchi, as did diol-epoxides of benzo[a]pyrene, while benzo[a]pyrene itself was inert [16].
  • 1,6-Dinitropyrene (DNP) was found to be an extremely potent genotoxicant in metabolically competent primary cultures of human and rat hepatocytes [10].
  • Genotoxicity of 1,3- and 1,6-dinitropyrene: induction of micronuclei in a panel of mammalian test cell lines [17].
  • In these experiments, 1,6-dinitropyrene was implanted into the lungs of rats according to a protocol known to induce lung tumors; the DNA adducts were characterized and quantified in target (lung) and surrogate (liver, white blood cells, and spleen lymphocytes) tissues [18].

Associations of CCRIS 2212 with other chemical compounds


Gene context of CCRIS 2212


Analytical, diagnostic and therapeutic context of CCRIS 2212


  1. Induction of squamous cell carcinoma in the rat lung by 1,6-dinitropyrene. Maeda, T., Izumi, K., Otsuka, H., Manabe, Y., Kinouchi, T., Ohnishi, Y. J. Natl. Cancer Inst. (1986) [Pubmed]
  2. 1,6-Dinitropyrene: mutagenicity in Salmonella and carcinogenicity in BALB/c mice. Tokiwa, H., Otofuji, T., Horikawa, K., Kitamori, S., Otsuka, H., Manabe, Y., Kinouchi, T., Ohnishi, Y. J. Natl. Cancer Inst. (1984) [Pubmed]
  3. Arylamines suppress their own activation and that of nitroarenes in V79 Chinese hamster cells by competing for acetyltransferases. Kiefer, F., Cumpelik, O., Reen, R., Doehmer, J., Wiebel, F.J. Environ. Health Perspect. (1994) [Pubmed]
  4. Active H-ras and N-ras in rat fibrosarcomas induced by 1,6-dinitropyrene. Ishizaka, Y., Ochiai, M., Ohgaki, H., Ishikawa, F., Sato, S., Miura, Y., Nagao, M., Sugimura, T. Cancer Lett. (1987) [Pubmed]
  5. Metabolic activation of 1-nitropyrene and 1,6-dinitropyrene by nitroreductases from Bacteroides fragilis and distribution of nitroreductase activity in rats. Kinouchi, T., Ohnishi, Y. Microbiol. Immunol. (1986) [Pubmed]
  6. DNA adduct formation and T-lymphocyte mutation induction in F344 rats implanted with tumorigenic doses of 1,6-dinitropyrene. Smith, B.A., Fullerton, N.F., Heflich, R.H., Beland, F.A. Cancer Res. (1995) [Pubmed]
  7. Inactivation of 1,3-, 1,6-, and 1,8-dinitropyrene by cytochrome P-450 enzymes in human and rat liver microsomes. Shimada, T., Guengerich, F.P. Cancer Res. (1990) [Pubmed]
  8. Kinds of mutations found when a shuttle vector containing adducts of 1,6-dinitropyrene replicates in human cells. Boldt, J., Mah, M.C., Wang, Y.C., Smith, B.A., Beland, F.A., Maher, V.M., McCormick, J.J. Carcinogenesis (1991) [Pubmed]
  9. DNA binding by 1-nitropyrene and 1,6-dinitropyrene in vitro and in vivo: effects of nitroreductase induction. Djurić, Z., Fifer, E.K., Yamazoe, Y., Beland, F.A. Carcinogenesis (1988) [Pubmed]
  10. Induction of DNA repair in human and rat hepatocytes by 1,6-dinitropyrene. Butterworth, B.E., Earle, L.L., Strom, S., Jirtle, R., Michalopoulos, G. Mutat. Res. (1983) [Pubmed]
  11. The clastogenic activity of dinitropyrenes in a rat-liver epithelial cell line. Danford, N., Wilcox, P., Parry, J.M. Mutat. Res. (1982) [Pubmed]
  12. 1,6-Dinitropyrene causes spindle disturbances and chromosomal damage in V79 Chinese hamster cells. Bauchinger, M., Schmid, E., Wiebel, F.J., Roscher, E. Mutat. Res. (1988) [Pubmed]
  13. In vivo mutagenesis in the lungs of gpt-delta transgenic mice treated intratracheally with 1,6-dinitropyrene. Hashimoto, A.H., Amanuma, K., Hiyoshi, K., Takano, H., Masumura, K., Nohmi, T., Aoki, Y. Environ. Mol. Mutagen. (2006) [Pubmed]
  14. The effects of 1,6-dinitropyrene on spindle morphology in transformed human cells. Adams, K., Lafi, A., Parry, J.M. Mutat. Res. (1989) [Pubmed]
  15. Formation of DNA adducts and induction of mutations in rats treated with tumorigenic doses of 1,6-dinitropyrene. Beland, F.A., Fullerton, N.F., Smith, B.A., Heflich, R.H. Environ. Health Perspect. (1994) [Pubmed]
  16. Biological actions of nitroarenes in short-term tests on Salmonella, cultured mammalian cells and cultured human tracheal tissues: possible basis for regulatory control. Sugimura, T., Takayama, S. Environ. Health Perspect. (1983) [Pubmed]
  17. Genotoxicity of 1,3- and 1,6-dinitropyrene: induction of micronuclei in a panel of mammalian test cell lines. Roscher, E., Wiebel, F.J. Mutat. Res. (1992) [Pubmed]
  18. DNA adduct formation and T lymphocyte mutation induction in F344 rats implanted with tumorigenic doses of 1,6-dinitropyrene. Beland, F.A. Research report (Health Effects Institute) (1995) [Pubmed]
  19. DNA adducts from nitroreduction of 2,7-dinitrofluorene, a mammary gland carcinogen, catalyzed by rat liver or mammary gland cytosol. Ritter, C.L., Culp, S.J., Freeman, J.P., Marques, M.M., Beland, F.A., Malejka-Giganti, D. Chem. Res. Toxicol. (2002) [Pubmed]
  20. Analysis of mutations in the K-ras and p53 genes of lung tumors and in the hprt gene of 6-thioguanine-resistant T-lymphocytes from rats treated with 1,6-dinitropyrene. Smith, B.A., Manjanatha, M.G., Pogribny, I.P., Mittelstaedt, R.A., Chen, T., Fullerton, N.F., Beland, F.A., Heflich, R.H. Mutat. Res. (1997) [Pubmed]
  21. Moderate inhibition of mutagenicity and carcinogenicity of benzo[a]pyrene, 1,6-dinitropyrene and 3,9-dinitrofluoranthene by Chinese medicinal herbs. Horikawa, K., Mohri, T., Tanaka, Y., Tokiwa, H. Mutagenesis (1994) [Pubmed]
  22. Differences in reduction of 1,6-dinitropyrene and 1-nitro-6-nitrosopyrene by rat liver cytosolic enzymes and formation of oxygen-reactive metabolites by nitrosoreduction. Djuric, Z., McGunagle, D.L. Cancer Lett. (1989) [Pubmed]
  23. Formation of DNA adducts and oxidative DNA damage in rats treated with 1,6-dinitropyrene. Djurić, Z., Potter, D.W., Culp, S.J., Luongo, D.A., Beland, F.A. Cancer Lett. (1993) [Pubmed]
  24. The clastogenic activity of 1,6-dinitropyrene in peripheral human lymphocytes. Adams, K., Lafi, A., Parry, J.M. Mutat. Res. (1988) [Pubmed]
  25. Effect of enzyme inducers on metabolism of 1-nitropyrene in human hepatoma cell line HepG2. Belisario, M.A., Arena, A.R., Pecce, R., Borgia, R., Staiano, N., De Lorenzo, F. Chem. Biol. Interact. (1991) [Pubmed]
  26. Arylamine N-acetyltransferase activities in cell lines of mouse, rat, hamster and man differing in their sensitivity to 1,6-dinitropyrene. Srivastava, A.K., Wiebel, F.J. Toxicol. Lett. (1990) [Pubmed]
  27. Carcinogen-DNA adduct formation in the lungs and livers of preweanling CD-1 male mice following administration of [3H]-6-nitrochrysene, [3H]-6-aminochrysene, and [3H]-1,6-dinitropyrene. Delclos, K.B., Walker, R.P., Dooley, K.L., Fu, P.P., Kadlubar, F.F. Cancer Res. (1987) [Pubmed]
  28. The efficiency of solvent extraction of mutagenic compounds in particulates exhausted from a small diesel engine. Tahara, I., Kinouchi, T., Kataoka, K., Ohnishi, Y. Tokushima J. Exp. Med. (1994) [Pubmed]
  29. DNA binding by 1-nitropyrene and dinitropyrenes in vitro and in vivo: effects of nitroreductase induction. Beland, F.A. Research report (Health Effects Institute) (1989) [Pubmed]
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