• 1
    Conney AH. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A. Clowes memorial lecture. Cancer Res 1982; 4: 4875917.
  • 2
    Guengerich FP, Shimada T. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 1991; 4: 391407.
  • 3
    Shimada T, Hayes CL, Yamazaki H, Amin S, Hecht SS, Guengerich FP, Sutter TR. Activation of chemically diverse procarcinogens by human cytochrome P450 1B1. Cancer Res 1996; 56: 297984.
  • 4
    Shimada T, Iwasaki M, Martin MV, Guengerich FP. Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA1535/pSK1002. Cancer Res 1989; 49: 321828.
  • 5
    Yamazaki H, Inui Y, Yun CH, Guengerich FP, Shimada T. Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-ni-trosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 1992; 13: 178994.
  • 6
    Guengerich FP, Kim DH, Iwasaki M. Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 1991; 1: 16879.
  • 7
    Shimada T, Guengerich FP. Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Proc Natl Acad Sci USA 1989; 86: 4625.
  • 8
    Imaoka S, Hiroi T, Tamura Y, Yamazaki H, Shimada T, Komori M, Degawa M, Funae Y. Mutagenic activation of 3-methoxy-4-aminoazobenzene by mouse renal cytochrome P450 CYP4B1: cloning and characterization of mouse CYP4B1. Arch Biochem Biophys 1995; 321: 25562.
  • 9
    Spink DC, Spink BC, Cao JQ, de Pasquale JA, Pentecost BT, Fasco MJ, Li Y, Sutter TR. Differential expression of CYP1A1 and CYP1B1 in human breast epithelial cells and breast tumor cells. Carcinogenesis 1998; 19: 2918.
  • 10
    Gelboin HV. Benzo[a]pyrene metabolism, activation, and carcinogenesis: role and regulation of mixed-function oxidases and related enzymes. Physiol Rev 1980; 60: 110766.
  • 11
    Tang M-shong, Vulimiri SV, Viaje A, Chen JX, Bilolikar DS, Morris RJ, Harvey RG, Slaga TJ, DiGiovanni J. Both (±)syn- and (±)anti-7,12-dimeth-ylbenz[a]anthracene-3,4-diol-1,2-epoxides initiate tumors in mouse skin that possess -CAA- to CTA- mutations at codon 61 of c-H-ras. Cancer Res 2000; 60: 568895.
  • 12
    Buening MK, Wislocki PG, Levin W, Yagi H, Thakker DR, Akagi H, Koreeda M, Jerina DM, Conney AH. Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7β,8α-dihydroxy-9α,10a-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Proc Natl Acad Sci USA 1978; 75: 535861.
  • 13
    Kapitulnik J, Levin W, Conney AH, Yagi H, Jerina DM. Benzo[a]pyrene7,8-dihydrodiol is more carcinogenic than benzo[a]pyrene in newborn mice. Nature 1977; 266: 37880.
  • 14
    Luch A, Schober W, Soballa VJ, Raab G, Greim H, Jacob J, Doehmer J, Seidel A. Metabolic activation of dibenzo[a, l]pyrene by human cytochrome P450 1A1 and 1B1 expressed in V79 Chinese hamster cells. Chem Res Toxicol 1999; 12: 35364.
  • 15
    Yang SK. Stereoselectivity of cytochrome P-450 isozymes and epoxide hydrolase in the metabolism of polycyclic aromatic hydrocarbons. Biochem Pharmacol 1988; 37: 6170.
  • 16
    Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EMJ, Inoue K. Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis 1999; 20: 160713.
  • 17
    Otto S, Bhattacharyya KK, Jefcoate CR. Polycyclic aromatic hydrocarbon metabolism in rat adrenal, ovary, and testis microsomes is catalyzed by the same novel cytochrome P450 (P450RAP). Endocrinology 1992; 131: 306776.
  • 18
    Savas U, Bhattacharyya KK, Christou M, Alexander DL, Jefcoate CR. Mouse cytochrome P-450EF, representative of a new 1B subfamily of cytochrome P-450s. J Biol Chem 1994; 269: 1490511.
  • 19
    Savas U, Carstens C-P, Jefcoate CR. Recombinant mouse CYP1B1 expressed in Escherichia coli exhibits selective binding by polycyclic hydrocarbons and metabolism which parallels C3H10T1/2 cell microsomes, but differs from human recombinant CYP1B1. Arch Biochem Biophys 1997; 347: 18192.
  • 20
    Walker NJ, Gastel JA, Costa LT, Clark GC, Lucier GW, Sutter TR. Rat CYP1B1: an adrenal cytochrome P450 that exhibits sex dependent expression in livers and kidneys of TCDD-treated animals. Carcinogenesis 1995; 16: 131927.
  • 21
    Sutter TR, Guzman K, Dold KM, Greenlee WF. Targets for dioxin: genes for plasminogen activator inhibitor-2 and interleukin-1β. Science 1995; 254: 4158.
  • 22
    Shimada T, Wunsch RM, Hanna IH, Sutter TR, Guengerich FP, Gillam EMJ. Recombinant human cytochrome P450 1B1 expression in Escherichia coli. Arch Biochem Biophys 1998; 357: 11120.
  • 23
    Shimada T, Oda Y, Inoue K. Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella. Drug Metab Dispos 2001; 29: 117682.
  • 24
    Buters JTM, Sakai S, Richter T, Pineau T, Alexander DL, Savas U, Doehmer J, Ward JM, Jefcoate CR, Gonzalez FJ. Cytochrome P450 CYP1B1 determines susceptibility to 7,12-dimethylbenz[a]anthracene-induced lymphomas. Proc Natl Acad Sci USA 1999; 96: 197782.
  • 25
    Buters JTM, Mahadevan B, Quintanilla-Martinez L, Gonzalez FJ, Greim H, Baird WM, Luch A. Cytochrome P450 1B1 determines susceptibility to dibenzo[a, l]pyrene-induced tumor formation. Chem Res Toxicol 2002; 15: 112735.
  • 26
    Hankinson O. The aryl hydrocarbon receptor complex. Annu Rev Pharmacol Toxicol 1995; 35: 30740.
  • 27
    Zhang L, Savas U, Alexander DL, Jefcoate CR. Characterization of the mouse Cyp1B1 gene: identification of an enhancer region that directs aryl hydrocarbon receptor-mediated constitutive and induced expression. J Biol Chem 1998; 273: 517483.
  • 28
    Sogawa K, Fujisawa-Sehara A, Yamane M, Fujii-Kuriyama Y. Location of regulatory elements responsible for drug induction in the rat cytochrome P-450c gene. Proc Natl Acad Sci USA 1986; 83: 80448.
  • 29
    Kubota M, Sogawa K, Kaizu Y, Sawaya T, Watanabe J, Kawajiri K, Gotoh O, Fujii-Kuriyama Y. Xenobiotic responsive element in the 5′-upstream region of the human P-450c gene. J Biochem (Tokyo) 1991; 110: 2326.
  • 30
    Eltom SE, Larsen MC, Jefcoate CR. Expression of CYP1B1 but not CYP1A1 by primary cultured human mammary stromal fibroblasts constitutively and in response to dioxin exposure: role of the Ah receptor. Carcinogenesis 1998; 19: 143744.
  • 31
    Kress S, Greenlee WF. Cell-specific regulation of human CYP1A1 and CYP1B1 genes. Cancer Res 1997; 57: 12649.
  • 32
    Sutter TR, Tang YM, Hayes CL, Wo Y-Y P, Jabs W, Li X, Yin H, Cody CW, Greenlee WF. Complete cDNA sequence of a human dioxin-inducible mRNA identifies a new gene subfamily of cytochrome P450 that maps to chromosome 2. J Biol Chem 1994; 269: 130929.
  • 33
    Eltom SE, Zhang L, Jefcoate CR. Regulation of cytochrome P-450 (CYP) 1B1 in mouse hepa-1 variant cell lines: a possible role for aryl hydrocarbon receptor nuclear translocator (ARNT) as a suppressor of CYP1B1 gene expression. Mol Pharmacol 1999; 55: 594604.
  • 34
    Warker NJ, Portier CJ, Lax SF, Crofts FG, Li Y, Lucier GW, Sutter TR. Characterization of the dose-response of CYP1B1, CYP1A1, and CYP1A2 in the liver of female Sprague-Dawley rats following chronic eposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin. Toxicol Appl Pharmacol 1999; 154: 27986.
  • 35
    Savas U, Jefcoate CR. Dual regulation of cytochrome P450EF expression via the aryl hydrocarbon receptor and protein stabilization in C3H/10T1 /2 cells. Mol Pharmacol 1994; 45: 11539.
  • 36
    Dohr O, Vogel C, Abel J. Different response of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-sensitive genes in human breast cancer MCF-7 and MDA-MB 231 cells. Arch Biochem Biophys 1995; 321: 40512.
  • 37
    Takahashi Y, Nakayama K, Itoh S, Fujii-Kuriyama Y, Kamataki T. Inhibition of the transcription of CYP1A1 gene by the upstream stimulatory factor 1 in rabbits. J Biol Chem 1997; 272: 3002531.
  • 38
    Shimizu Y, Nakatsuru Y, Ichinose M, Takahashi Y, Kume H, Mimura J, Fujii-Kuriyama Y, Ishikawa T. Benzo[a]pyrene carcinogenicity is lost in mice lacking the aryl hydrocarbon receptor. Proc Natl Acad Sci USA 2000; 97: 77982.
  • 39
    Shimada T, Inoue K, Suzuki Y, Kawai T, Azuma E, Nakajima T, Shindo M, Kurose K, Sugie A, Yamagishi Y, Fujii-Kuriyama Y, Hashimoto M. Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2, and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice. Carcinogenesis 2002; 23: 1199207.
  • 40
    Shimada T, Sugie A, Shindo M, Nakajima T, Azuma E, Hashimoto M, Inoue K. Tissue-specific induction of cytochromes P450 1A1 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in engineered C57BL/6J mice of Arylhydrocarbon Receptor gene. Toxicol Appl Pharmacol 2003; 187: 110.
  • 41
    Shimada T, Gillam EMJ, Oda Y, Tsumura F, Sutter TR, Guengerich FP, Inoue K. Metabolism of benzo[a]pyrene to trans-7,8-dihydroxy-7,8-dihy-drobenzo[a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase. Chem Res Toxicol 1999; 12: 6239.
  • 42
    Uno S, Dalton TP, Shertzer HG, Genter MB, Warshawsky D, Talaska G, Nebert DW. Benzo[a]pyrene-induced toxicity: paradoxical protection in Cyp1a1 (-/-) knockout mice having increased hepatic BaP-DNA adduct levels. Biochem Biophys Res Commun 2001; 289: 104956.
  • 43
    Nakachi K, Imai K, Hayashi S, Kawajiri K. Polymorphisms of the CYP1A1 and glutathione S-transferase genes associated with susceptibility to lung cancer in relation to cigarette dose in a Japanese population. Cancer Res 1993; 53: 29949.
  • 44
    Watanabe J, Shimada T, Gillam EMJ, Ikuta T, Suemasu K, Higashi Y, Gotoh O, Kawajiri K. Association of CYP1B1 genetic polymorphism with incidence to breast and lung cancer. Pharmacogenetics 2000; 10: 2533.
  • 45
    Kelsey KT, Wiencke JK, Spitz MR. A race-specific genetic polymorphism in the CYP1A1 gene is not associated with lung cancer in African Americans. Carcinogenesis 1994; 15: 11214.
  • 46
    Nebert DW, Ingelman-Sundberg M, Daly AK. Genetic epidemiology of environmental toxicity and cancer susceptibility: human allelic polymorphisms in drug metabolizing enzyme genes, their functional importance, and nomenclature issues. Drug Metab Rev 1999; 31: 46787.
  • 47
    Inoue K, Asao T, Shimada T. Ethnic-related differences in the frequency distribution of genetic polymorphisms in the CYP1A1 and CYP1B1 genes in Japanese and Caucasian populations. Xenobiotica 2000; 30: 28595.
  • 48
    Komori M, Kikuti O, Kitada T, Kamataki T. Molecular cloning of monkey P450 1A1 cDNA and expression in yeast. Biochim Biophys Acta 1992; 1131: 239.
  • 49
    Guo Z, Gillam E, Ohmori S, Tukey RH, Guengerich FP. Expression of modified human cytochrome P450 1A1 in Escherichia coli: effects of 5′ substitution, stabilization, purification, spectral characterization, and catalytic properties. Arch Biochem Biophys 1994; 312: 43646.
  • 50
    Shimada T, El-Bayoumy K, Upadhyaya P, Sutter TR, Guengerich FP, Yamazaki H. Inhibition of human cytochrome P450-catalyzed oxidations of xenobiotics and procarcinogens by synthetic organoselenium compounds. Cancer Res 1997; 57: 475764.
  • 51
    Shimada T, Yamazaki H, Foroozesh M, Hopkins NE, Alworth WL, Guengerich FP. Selectivity of polycyclic inhibitors for human cytochromes P450 1A1, 1A2, and 1B1. Chem Res Toxicol 1998; 11: 104856.
  • 52
    Chun YJ, Kim MY, Guengerich FP. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem Biophys Res Commun 1999; 262: 204.
  • 53
    Chun Y-J, Kim S, Kim D, Lee S-K, Guengerich FP. A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis. Cancer Res 2001; 61: 816470.
  • 54
    Kinoshita N, Gelboin HV. Aryl hydrocarbon hydroxylase and polycyclic hydrocarbon tumorigenesis: effect of the enzyme inhibitor 7,8-benzoflavone on tumorigenesis and macromolecule binding. Proc Natl Acad Sci USA 1972; 69: 8248.
  • 55
    El-Bayoumy K, Chae Y-H, Upadhyaya P, Meschter C, Cohen LA, Reddy BS. Inhibition of 7,12-dimethylbenzo[a]anthracene-induced tumors and DNA adduct formation in the mammary glands of female Sprague-Dawley rats by the synthetic organoselenium compound, 1,4-phenylenebis(methylene)selenocyanate. Cancer Res 1992; 52: 24027.
  • 56
    El-Bayoumy K, Upadhyaya P, Chae Y-H, Sohn O-S, Rao CV, Faila E, Reddy BS. Chemoprevention of cancer by organoselenium compounds. J Cell Biochem 1995; 22: 92100.
  • 57
    Viaje A, Lu J-Y L, Hopkins NE, Nettikumara AN, DiGiovanni J, Alworth WL, Slaga TJ. Inhibition of the binding of 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene to DNA in mouse skin epidermis by 1-ethynylpyrene. Carcinogenesis 1990; 11: 113943.
  • 58
    Alworth WL, Viaje A, Sandoval A, Warren BS, Slaga TJ. Potent inhibitory effects of suicide inhibitors of P450 isozyme on 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene initiated skin tumors. Carcinogenesis 1991; 12: 120915.
  • 59
    Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Fransworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997; 275: 21820.