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Chemical Compound Review

NITROPYRENE     1-nitropyrene

Synonyms: CCRIS 455, CHEMBL167395, ACMC-1B96I, N22959_ALDRICH, AG-F-92843, ...
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Disease relevance of NITROPYRENE


High impact information on NITROPYRENE


Chemical compound and disease context of NITROPYRENE


Biological context of NITROPYRENE


Anatomical context of NITROPYRENE


Associations of NITROPYRENE with other chemical compounds


Gene context of NITROPYRENE


Analytical, diagnostic and therapeutic context of NITROPYRENE

  • To elucidate a relationship between lung cancer and tumor induction of environmental chemicals, the presence of 1-nitropyrene (1-NP) and benzo[a]pyrene (B[a]P) in 137 Japanese (97 male and 40 female), and 21 Chinese lung specimens was examined by HPLC, and GC-MS and environmental exposure discussed [30].
  • Competitive ELISA with antibody 11H2 reliably detected AP-DNA adducts formed when 1-nitropyrene was incubated with Salmonella typhimurium TA1538 [31].
  • The urinary and fecal metabolites of NP were separated and quantitated by h.p.l.c., then identified by high resolution gas chromatography/mass spectrometry (h.r.g.c./m.s.) and comparison with synthetic reference compounds, where available [32].
  • An oligodeoxyribonucleotide 5'-d(CTCATGAPATTCC), in which G(AP) denotes N-(guanin-8-yl)-1-aminopyrene, the C8-guanine adduct of reductively activated 1-nitropyrene, was synthesized and characterized by polyacrylamide gel electrophoresis, absorption and fluorescence spectroscopy, circular dichroism, and thermal melting studies [33].
  • In this study, lung lesions were found in male A/J mice 24 wk after intraperitoneal injection of 1-nitropyrene (1-NP) [34].


  1. Formation of DNA adducts in vitro and in Salmonella typhimurium upon metabolic reduction of the environmental mutagen 1-nitropyrene. Howard, P.C., Heflich, R.H., Evans, F.E., Beland, F.A. Cancer Res. (1983) [Pubmed]
  2. Mutagenicity, unscheduled DNA synthesis, and metabolism of 1-nitropyrene in the human hepatoma cell line HepG2. Eddy, E.P., Howard, P.C., McCoy, G.D., Rosenkranz, H.S. Cancer Res. (1987) [Pubmed]
  3. Comparative carcinogenicities of 1-, 2-, and 4-nitropyrene and structurally related compounds in the female CD rat. Imaida, K., Hirose, M., Tay, L., Lee, M.S., Wang, C.Y., King, C.M. Cancer Res. (1991) [Pubmed]
  4. Mutagenic specificity of reductively activated 1-nitropyrene in Escherichia coli. Malia, S.A., Basu, A.K. Biochemistry (1995) [Pubmed]
  5. 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]
  6. Kinds and locations of mutations induced in the hypoxanthine-guanine phosphoribosyltransferase gene of human T-lymphocytes by 1-nitrosopyrene, including those caused by V(D)J recombinase. McGregor, W.G., Maher, V.M., McCormick, J.J. Cancer Res. (1994) [Pubmed]
  7. Cytochrome P-450 3A4 (nifedipine oxidase) is responsible for the C-oxidative metabolism of 1-nitropyrene in human liver microsomal samples. Silvers, K.J., Chazinski, T., McManus, M.E., Bauer, S.L., Gonzalez, F.J., Gelboin, H.V., Maurel, P., Howard, P.C. Cancer Res. (1992) [Pubmed]
  8. Pathways for the mutagenesis of 1-nitropyrene and dinitropyrenes in the human hepatoma cell line HepG2. Silvers, K.J., Eddy, E.P., McCoy, E.C., Rosenkranz, H.S., Howard, P.C. Environ. Health Perspect. (1994) [Pubmed]
  9. Identification of two N2-deoxyguanosinyl DNA adducts upon nitroreduction of the environmental mutagen 1-nitropyrene. Herreno-Saenz, D., Evans, F.E., Beland, F.A., Fu, P.P. Chem. Res. Toxicol. (1995) [Pubmed]
  10. Bioactivation of cysteine conjugates of 1-nitropyrene oxides by cysteine conjugate beta-lyase purified from Peptostreptococcus magnus. Kataoka, K., Kinouchi, T., Akimoto, S., Ohnishi, Y. Appl. Environ. Microbiol. (1995) [Pubmed]
  11. The nature of the mutagenicity and carcinogenicity of nitrated, aromatic compounds in the environment. Tokiwa, H., Nakagawa, R., Horikawa, K., Ohkubo, A. Environ. Health Perspect. (1987) [Pubmed]
  12. Metabolism of nitropolycyclic aromatic hydrocarbons by human intestinal microflora. Cerniglia, C.E., Howard, P.C., Fu, P.P., Franklin, W. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  13. Species differences in metabolic activation and inactivation of 1-nitropyrene in the liver. Kataoka, K., Kinouchi, T., Ohnishi, Y. Cancer Res. (1991) [Pubmed]
  14. Participation of cytochrome P-450 in reductive metabolism of 1-nitropyrene by rat liver microsomes. Saito, K., Kamataki, T., Kato, R. Cancer Res. (1984) [Pubmed]
  15. Comparative mutagenesis of the C8-guanine adducts of 1-nitropyrene and 1,6- and 1,8-dinitropyrene in a CpG repeat sequence. A slipped frameshift intermediate model for dinucleotide deletion. Hilario, P., Yan, S., Hingerty, B.E., Broyde, S., Basu, A.K. J. Biol. Chem. (2002) [Pubmed]
  16. 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]
  17. Kinetics and cofactor requirements for the nitroreductive metabolism of 1-nitropyrene and 3-nitrofluoranthene by rabbit liver aldehyde oxidase. Bauer, S.L., Howard, P.C. Carcinogenesis (1991) [Pubmed]
  18. Induction of rat mammary gland tumors by 1-nitropyrene, a recently recognized environmental mutagen. Hirose, M., Lee, M.S., Wang, C.Y., King, C.M. Cancer Res. (1984) [Pubmed]
  19. Synthesis and mutagenicity of 1-nitro-6-nitrosopyrene and 1-nitro-8-nitrosopyrene, potential intermediates in the metabolic activation of 1,6- and 1,8-dinitropyrene. Fifer, E.K., Heflich, R.H., Djurić, Z., Howard, P.C., Beland, F.A. Carcinogenesis (1986) [Pubmed]
  20. Transformation of normal human skin fibroblasts by 1-nitropyrene and 6-nitrobenzo[a]pyrene. Howard, P.C., Gerrard, J.A., Milo, G.E., Fu, P.P., Beland, F.A., Kadlubar, F.F. Carcinogenesis (1983) [Pubmed]
  21. Identification of ring oxidized metabolites of 1-nitropyrene in the feces and urine of germfree F344 rats. El-Bayoumy, K., Reddy, B., Hecht, S.S. Carcinogenesis (1984) [Pubmed]
  22. 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]
  23. Tumorigenicity of nitrated derivatives of pyrene, benz[a]anthracene, chrysene and benzo[a]pyrene in the newborn mouse assay. Wislocki, P.G., Bagan, E.S., Lu, A.Y., Dooley, K.L., Fu, P.P., Han-Hsu, H., Beland, F.A., Kadlubar, F.F. Carcinogenesis (1986) [Pubmed]
  24. A new Salmonella typhimurium NM5004 strain expressing rat glutathione S-transferase 5-5: use in detection of genotoxicity of dihaloalkanes using an SOS/umu test system. Oda, Y., Yamazaki, H., Thier, R., Ketterer, B., Guengerich, F.P., Shimada, T. Carcinogenesis (1996) [Pubmed]
  25. 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]
  26. 1-Nitropyrene induces elevated expression of oncogenes and tumor suppressor genes 24 hours after treatment in CBA/Ca mice. Ember, I., Pusztai, Z., Gyöngyi, Z., Kiss, I. Anticancer Res. (2000) [Pubmed]
  27. Induction of CYP1A1, CYP1A2, and CYP1B1 mRNAs by nitropolycyclic aromatic hydrocarbons in various human tissue-derived cells: chemical-, cytochrome P450 isoform-, and cell-specific differences. Iwanari, M., Nakajima, M., Kizu, R., Hayakawa, K., Yokoi, T. Arch. Toxicol. (2002) [Pubmed]
  28. Polycyclic aromatic hydrocarbon carcinogens increase ubiquitination of p21 protein after the stabilization of p53 and the expression of p21. Nakanishi, Y., Pei, X.H., Takayama, K., Bai, F., Izumi, M., Kimotsuki, K., Inoue, K., Minami, T., Wataya, H., Hara, N. Am. J. Respir. Cell Mol. Biol. (2000) [Pubmed]
  29. Effects of DNA repair deficiency on the mutational specificity in the lacZ gene of Escherichia coli. Watanabe-Akanuma, M., Ohta, T. Mutat. Res. (1994) [Pubmed]
  30. The presence of mutagens/carcinogens in the excised lung and analysis of lung cancer induction. Tokiwa, H., Sera, N., Horikawa, K., Nakanishi, Y., Shigematu, N. Carcinogenesis (1993) [Pubmed]
  31. Monoclonal antibodies to 1-aminopyrene-DNA. Hsieh, L.L., Jeffrey, A.M., Santella, R.M. Carcinogenesis (1985) [Pubmed]
  32. Metabolism of 1-nitro[14C]pyrene in vivo in the rat and mutagenicity of urinary metabolites. Ball, L.M., Kohan, M.J., Inmon, J.P., Claxton, L.D., Lewtas, J. Carcinogenesis (1984) [Pubmed]
  33. Solution properties and computational analysis of an oligodeoxynucleotide containing N-(deoxyguanosin-8-yl)-1-aminopyrene. Nolan, S.J., Vyas, R.R., Hingerty, B.E., Ellis, S., Broyde, S., Shapiro, R., Basu, A.K. Carcinogenesis (1996) [Pubmed]
  34. Ki-ras mutation and cell proliferation of lung lesions induced by 1-nitropyrene in A/J mice. Bai, F., Nakanishi, Y., Takayama, K., Pei, X.H., Tokiwa, H., Hara, N. Mol. Carcinog. (1998) [Pubmed]
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