Lack of contribution of covalent benzo[a]pyrene-7,8-quinone–DNA adducts in benzo[a]pyrene-induced mouse lung tumorigenesis

Cook, 1933, The isolation of a cancer producing hydrocarbon from coal tar, J. Chem. Soc., 395, 10.1039/jr9330000395 Kennaway, 1955, Identification of carcinogenic compound in coal tar, Brit. Med. J., 2, 749, 10.1136/bmj.2.4942.749 IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Polynuclear Aromatic Compounds, Part 1, Chemical, Environmental, and Experimental Data, International Agency for Research on Cancer, Lyon, France, 1983. Dipple, 1985, Polycyclic aromatic hydrocarbon carcinogenesis: an introduction, 1 Osborne, 1987 IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Polynuclear Aromatic Compounds, Part 3, Industrial Exposures in Aluminum Production, Coal Gasification, Coke Production, and Iron and Steel Founding, International Agency for Research on Cancer, Lyon, France, 1984. IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Polynuclear Aromatic Compounds, Part 4, Bitumens, Coal-Tars, and Derived Products, Shale Oils and Soots, International Agency for Research on Cancer, Lyon, France, 1985. IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Tobacco Smoking, International Agency for Research on Cancer, Lyon, France, 1986. IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Diesel and Gasoline Exhausts and Some Nitroarenes, International Agency for Research on Cancer, Lyon, France, 1989. Straif, 2005, Carcinogenicity of polycyclic aromatic hydrocarbons, Lancet Oncol., 6, 931, 10.1016/S1470-2045(05)70458-7 Xue, 2005, Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: a review, Toxicol. Appl. Pharmacol., 206, 73, 10.1016/j.taap.2004.11.006 Alexandrov, 2002, CYP1A1 and GSTM1 genotypes affect benzo[a]pyrene DNA adducts in smokers’ lung: comparison with aromatic/hydrophobic adduct formation, Carcinogenesis, 23, 1969, 10.1093/carcin/23.12.1969 Feng, 2002, Preferential DNA damage and poor repair determine ras gene mutational hotspot in human cancer, J. Natl. Cancer Inst., 94, 1527, 10.1093/jnci/94.20.1527 Hussain, 2001, Mutability of p53 hotspot codons to benzo(a)pyrene diol epoxide (BPDE) and the frequency of p53 mutations in nontumorous human lung, Cancer Res., 61, 6350 Krawczak, 1998, p53 mutations, benzo[a]pyrene and lung cancer, Mutagenesis, 13, 319, 10.1093/mutage/13.4.319 Liang, 2003, Identification of benzo(a)pyrene diol epoxide-binding DNA fragments using DNA immunoprecipitation technique, Cancer Res., 63, 1470 Rojas, 1998, High benzo[a]pyrene diol-epoxide DNA adduct levels in lung and blood cells from individuals with combined CYP1A1 MspI/Msp-GSTM1*0/*0 genotypes, Pharmacogenetics, 8, 109, 10.1097/00008571-199804000-00003 Xiong, 2001, Sensitivity to benzo(a)pyrene diol-epoxide associated with risk of breast cancer in young women and modulation by glutathione S-transferase polymorphisms: a case-control study, Cancer Res., 61, 8465 Cavalieri, 1995, Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons, Xenobiotica, 25, 677, 10.3109/00498259509061885 Flowers-Geary, 1995, Identification of benzo[a]pyrene-7,8-dione as an authentic metabolite of (+/−)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in isolated rat hepatocytes, Carcinogenesis, 16, 2707, 10.1093/carcin/16.11.2707 Penning, 1999, Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones, Chem. Res. Toxicol., 12, 1, 10.1021/tx980143n Nesnow, 2002, Comparison of the genotoxic activities of the K-region dihydrodiol of benzo[a]pyrene with benzo[a]pyrene in mammalian cells: morphological cell transformation; DNA damage; and stable covalent DNA adducts, Mutat. Res., 521, 91, 10.1016/S1383-5718(02)00218-8 Balu, 2004, Identification and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8-quinone from reactions at physiological pH, Chem. Res. Toxicol., 17, 827, 10.1021/tx034207s Balu, 2006, Benzo[a]pyrene-7,8-quinone-3′-mononucleotide adduct standards for 32P postlabeling analyses: detection of benzo[a]pyrene-7,8-quinone-calf thymus DNA adducts, Anal. Biochem., 355, 213, 10.1016/j.ab.2006.05.023 Murty, 1992, Characterization of mercapturic acid and glutathionyl conjugates of benzo[a]pyrene-7,8-dione by two-dimensional NMR, Bioconjug. Chem., 3, 218, 10.1021/bc00015a003 Murty, 1992, Polycyclic aromatic hydrocarbon (PAH) ortho-quinone conjugate chemistry: kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphthalene-1,2-dione, Chem. Biol. Interact., 84, 169, 10.1016/0009-2797(92)90077-X McCoull, 1999, Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7-guanine adducts, Chem. Res. Toxicol., 12, 237, 10.1021/tx980182z Shou, 1993, Reactivity of benzo[a]pyrene-7,8-dione with DNA. Evidence for the formation of deoxyguanosine adducts, Carcinogenesis, 14, 475, 10.1093/carcin/14.3.475 Harvey, 2005, Syntheses of adducts of active metabolites of carcinogenic polycyclic aromatic hydrocarbons with 2′-deoxyribonucleosides, Polycycl. Aromat. Compd., 25, 371, 10.1080/10406630500447019 Harvey, 2004, Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis, J. Org. Chem., 69, 2024, 10.1021/jo030348n Ross, 1991, DNA isolation from small tissue samples using salt and spermine, Nucleic Acids Res., 19, 6053, 10.1093/nar/19.21.6053 Ross, 1991, DNA adducts in rat lung, liver and peripheral blood lymphocytes produced by i.p. administration of benzo[a]pyrene metabolites and derivatives, Carcinogenesis, 12, 1953, 10.1093/carcin/12.10.1953 Nesnow, 1997, Comparison of the morphological transforming activities of dibenzo[a,l]pyrene and benzo[a]pyrene in C3H10T1/2CL8 cells and characterization of the dibenzo[a,l]pyrene-DNA adducts, Carcinogenesis, 18, 1973, 10.1093/carcin/18.10.1973 Cho, 1976, Synthesis of hydroquinone diacetates from polycyclic aromatic quinones, J. Chem. Soc., 836 Ross, 1999, Polycyclic aromatic hydrocarbons: correlations between DNA adducts and ras oncogene mutations, Mutat. Res., 424, 155, 10.1016/S0027-5107(99)00016-0 Denissenko, 1996, Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in P53, Science, 274, 430, 10.1126/science.274.5286.430 Denissenko, 1996, Site-specific induction and repair of benzo[a]pyrene diol epoxide DNA damage in human H-ras protooncogene as revealed by restriction cleavage inhibition, Mutat. Res., 363, 27, 10.1016/0921-8777(95)00059-3 Cavalieri, 1991, Comparative dose–response tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland, Carcinogenesis, 12, 1939, 10.1093/carcin/12.10.1939 Ross, 1995, Adenomas induced by polycyclic aromatic hydrocarbons in strain A/J mouse lung correlate with time-integrated DNA adduct levels, Cancer Res., 55, 1039 Fang, 2001, Identification and characterization of a novel benzo[a]pyrene-derived DNA adduct, Biochem. Biophys. Res. Commun., 281, 383, 10.1006/bbrc.2000.4161 Banasiewicz, 2004, Identification and quantitation of benzo[a]pyrene-derived DNA adducts formed at low adduction level in mice lung tissue, Anal. Biochem., 334, 390, 10.1016/j.ab.2004.08.006 Yeowell-O’Connell, 2001, Protein adducts of 1,4-benzoquinone and benzene oxide among smokers and nonsmokers exposed to benzene in China, Cancer Epidemiol. Biomarkers Prev., 10, 831 Lin, 2009, Investigation of the cumulative tissue doses of naphthoquinones in human serum using protein adducts as biomarker of exposure, Chem.-Biol. Interact., 181, 107, 10.1016/j.cbi.2009.05.016 Jiang, 2006, Competing roles of aldo-keto reductase 1A1 and cytochrome P4501B1 in benzo[a]pyrene-7,8-diol activation in human bronchoalveolar H358 cells: role of AKRs in P4501B1 induction, Chem. Res. Toxicol., 19, 68, 10.1021/tx0502488 Tsuruda, 2001, Stable expression of rat dihydrodiol dehydrogenase (AKR1C9) in human breast MCF-7 cells results in the formation of PAH-o-quinones and enzyme mediated cell death, Chem. Res. Toxicol., 14, 856, 10.1021/tx0100035 Jiang, 2005, Competing roles of cytochrome P450 1A1/1B1 and aldo-keto reductase 1A1 in the metabolic activation of (+/−)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in human bronchoalveolar cell extracts, Chem. Res. Toxicol., 18, 365, 10.1021/tx0497245 Park, 2008, Evidence for the aldo-keto reductase pathway of polycyclic aromatic trans-dihydrodiol activation in human lung A549 cells, Proc. Natl. Acad. Sci. U.S.A., 105, 6846, 10.1073/pnas.0802776105 Jiang, 2007, Metabolism of benzo[a]pyrene in human bronchoalveolar H358 cells using liquid chromatography-mass spectrometry, Chem. Res. Toxicol., 20, 1331, 10.1021/tx700107z Kim, 2000, Lipid peroxidation, antioxidant enzymes, and benzo[a]pyrene-quinones in the blood of rats treated with benzo[a]pyrene, Chem.-Biol. Interact., 127, 139, 10.1016/S0009-2797(00)00177-0 Mass, 1993, Ki-ras oncogene mutations in tumors and DNA adducts formed by benz[j]aceanthrylene and benzo[a]pyrene in the lungs of strain A/J mice, Mol. Carcinog., 8, 186, 10.1002/mc.2940080309 Leavitt, 2008, Mutations induced by benzo[a]pyrene and dibenzo[a,l]pyrene in lacI transgenic B6C3F1 mouse lung result from stable DNA adducts, Mutagenesis, 23, 445, 10.1093/mutage/gen033 Prahalad, 1997, Dibenzo[a,l]pyrene-induced DNA adduction, tumorigenicity, and Ki-ras oncogene mutations in strain A/J mouse lung, Carcinogenesis, 18, 1955, 10.1093/carcin/18.10.1955