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99. Devanesan, P.D., RamaKrishna, N.V.S., Todorovic, R., Rogan, E.G., Cavalieri, E.L., Jeong, H., Jankowiak, R., Small, G.J. (1992). Identi cation and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro. Chemical Research in Toxicology, 5, 302 309. 100. Chakravarti, D., Pelling, J.C., Cavalieri, E.L., Rogan, E.G. (1995). Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras-mutations in mouse skin papillomas: the role of apurinic sites. Proceedings of the National Academy of Sciences of the United States of America, 92, 10422 10426. 101. Jennette, K.W., Jeffery, A.M., Blobstein, S.H., Beland, F.A., Harvey, R.G., Weinstein, I.B. (1977). Nucleoside adducts from the in vitro reaction of benzo[a]pyrene7,8-dihydrodiol-9,10-oxide or benzo[a]pyrene-4,5-oxide with nucleic acids. Biochemistry, 16, 932 938. 102. Ruan, Q., Kim, H.-Y., Jiang, H., Penning, T.M., Harvey, R.G., Blair, I.A. (2006). Quanti cation of benzo[a]pyrene diol epoxide DNA-adducts by stable isotope dilution liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 20, 1369 1380. 103. Koreeda, M., Moore, P.D., Wislocki, P.G., Levin, W., Conney, A.H., Yagi, H., Jerina, D.M. (1978). Binding of benzo[a]pyrene-7,8-diol-9,10-epoxides to DNA, RNA and protein of mouse skin occurs with high stereoselectivity. Science, 199, 778 781. 104. Ruan, Q., Gelhaus, S.L., Penning, T.M., Harvey, R.G., Blair, I.A. (2007). Aldo-keto reductase- and cytochrome P450-dependent formation of benzo[a]pyrene-derived DNA adducts in human bronchoalveolar cells. Chemical Research in Toxicology, 20, 424 431. 105. Malaveille, C., Kuroki, T., Sims, P., Grover, P.L., Bartsch, H. (1977). Mutagenicity of isomeric diol-epoxides of benzo[a]pyrene and benz[a]anthracene in S. typhimurium TA98 and TA100 and in V79 Chinese hamster cells. Mutation Research, 44, 313 326. 106. Marshall, C.J., Vousden, K.H., Phillips, D.H. (1984). Activation of c-Ha-ras-1 proto-oncogene by in vitro chemical modi cation with a chemical carcinogen, benzo[a]pyrene diol-epoxide. Nature, 310, 585 589. 107. Denissenko, M.F., Pao, A., Tang, M-S, P eifer, G.P. (1996). Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in p53. Science, 274, 430 432. 108. Slaga, T.J., Viaje, A., Berry, D.L., Bracken, W. (1976). Skin tumour initiating ability of benzo[a]pyrene 4,5-, 7,5- and 7,8-diol-9,10-epoxides and 7,8-diol. Cancer Letters, 2, 115 122. 109. Slaga, T.J., Bracken, W.M., Viaje, A., Levin, W., Yagi, H., Jerina, D.M., Conney, A.H. (1977). Comparison of the tumour initiating activities of benzo[a]pyrene arene oxides and diol-epoxides. Cancer Research, 37, 4130 4133. 110. Nesnow, S., Mass, M.J., Ross, J.A., Galati, A.J., Lambert, G.R., Gennings, C., Carter, W.H., Jr, Stoner, G.A. (1998). Lung tumourigenic interactions in strain A/J mice of ve environmental polycyclic aromatic hydrocarbons. Environmental Health Perspectives, 106, 1337 1346. 111. Agency for Toxic Substances & Disease Registry (ASTDR) (1995). Toxicological Pro le for Polycyclic Aromatic Hydrocarbons (PAHs), ASTDR, pp. 50 53. 112. Burczynski, M.E., Harvey, R.G., Penning, T.M. (1998). Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms:
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oxidation of trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated oquinone metabolite benzo[a]pyrene-7,8-dione. Biochemistry, 37, 6781 6790. Palackal, N.T., Burczynski, M.E., Harvey, R.G., Penning, T.M. (2001). The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen transdihydrodiols to o-quinones: potential role in polycyclic aromatic hydrocarbon activation. Biochemistry, 40, 10901 10910. Palackal, N.T., Lee, S.H., Harvey, R.G., Blair, I.A., Penning, T.M. (2002). Activation of polycyclic aromatic hydrocarbon trans-dihydrodiol proximate carcinogens by human aldo-keto reductase (AKR1C) enzymes and their functional overexpression in human lung carcinoma (A549) cells. Journal of Biological Chemistry, 277, 24799 24808. Smithgall, T.E., Harvey, R.G., Penning, T.M. (1988). Spectroscopic identi cation of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. A potential route of proximate carcinogen metabolism. Journal of Biological Chemistry, 263, 1814 1820. Penning, T.M., Ohnishi, S.T., Ohnishi, T., Harvey, R.G. (1996). Generation of reactive oxygen species during the enzymatic oxidation of polycyclic aromatic hydrocarbon trans-dihydrodiols catalyzed by dihydrodiol dehydrogenase. Chemical Research in Toxicology, 9, 84 92. Shou, M., Harvey, R.G., Penning, T.M. (1993). Reactivity of benzo[a]pyrene-7,8dione with DNA. Evidence for the formation of deoxyguanosine adducts. Carcinogenesis, 14, 475 482. McCoull, K.D., Rindgen, D., Blair, I.A., Penning, T.M. (1998). Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7guanine adducts. Chemical Research in Toxicology, 12, 237 246. Balu, N., Padgett, W.T., Lambert, G.R., Swank, A.E., Richard, A.M., Nesnow, S. (2004). Identi cation and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8-quione from reactions at physiological pH. Chemical Research in Toxicology, 17, 827 838. Murty, V.S., Penning, T.M. (1992). Characterization of mercapturic acid and glutathionyl conjugates of benzo[a]pyrene-7,8-dione by two-dimensional NMR. Bioconjugate Chemistry, 3, 218 224. Sridhar, G.R., Murty, V.S., Lee, S.H., Blair, I.A., Penning, T.M. (2001). Amino acid adducts of PAH o-quinones: model studies with naphthalene-1,2-dione. Tetrahedron, 57, 407 412. Park, J.-H., Gopishetty, S., Szewczuk, L.M., Troxel, A.B., Harvey, R.G., Penning, T.M. (2005). Formation of 8-oxo-7,8-dihydro-2 -deoxyguanosine (8-oxo-dGuo) by PAH o-quinones: involvement of reactive oxygen species and copper (II)/copper(I) redox cycling. Chemical Research in Toxicology, 18, 1026 1037. Shen, Y.M., Troxel, A.B., Vedantam, S., Penning, T.M., Field, J. (2006). Comparison of p53 mutations induced by PAH o-quinones with those caused by antibenzo[a]pyrene diol epoxide in vitro: role of reactive oxygen and biological selection. Chemical Research in Toxicology, 19, 1441 1450. Flowers, L., Ohnishi, S.T., Penning, T.M. (1997). DNA strand scission by polycyclic aromatic hydrocarbon o-quinones: role of reactive oxygen species, Cu(II)/ Cu(I) redox-cycling and o-semiquinone anion radicals. Biochemistry, 36, 8640 8648.
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