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Volumn 105, Issue 19, 2008, Pages 6846-6851

Evidence for the aldo-keto reductase pathway of polycyclic aromatic trans-dihydrodiol activation in human lung A549 cells

Author keywords

8 oxo dGuo; DNA strand breaks; Reactive oxygen species; Tobacco carcinogens

Indexed keywords

4,5 DIHYDRO 4,5 DIHYDROXYBENZO[A]PYRENE; 7,8 DIHYDRO 7,8 DIHYDROXYBENZO[A]PYRENE; 7,8 DIHYDROXY 9ALPHA,10BETA EPOXY 7,8,9,10 TETRAHYDROBENZO[A]PYRENE; 8 HYDROXYGUANINE; 8 OXOGUANINE HYDROXYLASE; ALDO KETO REDUCTASE; BENZO[A]PYRENE 7,8 DIONE; BENZO[A]PYRENE DERIVATIVE; DICHLOROFLUORESCEIN; GLUTATHIONE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; OXIDOREDUCTASE; POLYCYCLIC AROMATIC HYDROCARBON; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; 8 OXO 7 HYDRODEOXYGUANOSINE; 8-OXO-7-HYDRODEOXYGUANOSINE; ALCOHOL DEHYDROGENASE; BENZO(A)PYRENE 7,8 DIHYDRODIOL; BENZO(A)PYRENE 7,8 DIONE; BENZO(A)PYRENE 7,8-DIHYDRODIOL; BENZO(A)PYRENE-7,8-DIONE; CARBONYL REDUCTASE (NADPH); CATECHOL METHYLTRANSFERASE; DEOXYGUANOSINE; DIACETYLDICHLOROFLUORESCEIN; DNA GLYCOSYLTRANSFERASE; DRUG DERIVATIVE; ENZYME INHIBITOR; FLUORESCEIN DERIVATIVE; ISOENZYME; OXOGUANINE GLYCOSYLASE 1, HUMAN;

EID: 44349169635     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0802776105     Document Type: Article
Times cited : (107)

References (41)
  • 1
    • 0016524263 scopus 로고
    • Polycyclic aromatic hydrocarbon profile analysis of high-protein foods, oils, and fats by gas chromatography
    • Grimmer G, Bohnke H (1975) Polycyclic aromatic hydrocarbon profile analysis of high-protein foods, oils, and fats by gas chromatography. J Assoc Off Anal Chem 58:725-733.
    • (1975) J Assoc Off Anal Chem , vol.58 , pp. 725-733
    • Grimmer, G.1    Bohnke, H.2
  • 2
    • 20444412643 scopus 로고    scopus 로고
    • Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review
    • Xue W, Warshawsky D (2005) Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review. Toxicol Appl Pharmacol 206:73-93.
    • (2005) Toxicol Appl Pharmacol , vol.206 , pp. 73-93
    • Xue, W.1    Warshawsky, D.2
  • 3
    • 0033591845 scopus 로고    scopus 로고
    • Tobacco smoke carcinogens and lung cancer
    • Hecht SS (1999) Tobacco smoke carcinogens and lung cancer. J Natl Cancer Inst 91:1194-1210.
    • (1999) J Natl Cancer Inst , vol.91 , pp. 1194-1210
    • Hecht, S.S.1
  • 4
    • 0021133140 scopus 로고
    • Activation of c-Ha-ras-1 protooncogene by in vitro modification with a chemical carcinogen, benzo(a)pyrene diol-epoxide
    • Marshall CJ, Vousden KH, Phillips DH (1984) Activation of c-Ha-ras-1 protooncogene by in vitro modification with a chemical carcinogen, benzo(a)pyrene diol-epoxide. Nature 310:586-589.
    • (1984) Nature , vol.310 , pp. 586-589
    • Marshall, C.J.1    Vousden, K.H.2    Phillips, D.H.3
  • 5
    • 0029806936 scopus 로고    scopus 로고
    • Preferential formation of benzo-[a]pyrene adducts at lung cancer mutational hotspots in P53
    • Denissenko MF, Pao A, Tang M, Pfeifer GP (1996) Preferential formation of benzo-[a]pyrene adducts at lung cancer mutational hotspots in P53. Science 274:430-432.
    • (1996) Science , vol.274 , pp. 430-432
    • Denissenko, M.F.1    Pao, A.2    Tang, M.3    Pfeifer, G.P.4
  • 6
    • 0020431144 scopus 로고    scopus 로고
    • Conney AH (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res 42:4875-4917.
    • Conney AH (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res 42:4875-4917.
  • 7
    • 0034556629 scopus 로고    scopus 로고
    • Error-prone lesion bypass by human DNA polymerase eta
    • Zhang Y, et al. (2000) Error-prone lesion bypass by human DNA polymerase eta. Nucleic Acids Res 28:4717-4724.
    • (2000) Nucleic Acids Res , vol.28 , pp. 4717-4724
    • Zhang, Y.1
  • 8
    • 0029080079 scopus 로고
    • Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons
    • Cavalieri EL, Rogan EG (1995) Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons. Xenobiotica 25:677-688.
    • (1995) Xenobiotica , vol.25 , pp. 677-688
    • Cavalieri, E.L.1    Rogan, E.G.2
  • 9
    • 0022432235 scopus 로고
    • Abasic sites from cytosine as termination signals for DNA synthesis
    • Sagher D, Strauss B (1985) Abasic sites from cytosine as termination signals for DNA synthesis. Nucleic Acids Res 13:4285-4298.
    • (1985) Nucleic Acids Res , vol.13 , pp. 4285-4298
    • Sagher, D.1    Strauss, B.2
  • 10
    • 0032937593 scopus 로고    scopus 로고
    • Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: Generation of reactive and redox active o-quinones
    • Penning TM, et al. (1999) Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: Generation of reactive and redox active o-quinones. Chem Res Toxicol 12:1-18.
    • (1999) Chem Res Toxicol , vol.12 , pp. 1-18
    • Penning, T.M.1
  • 11
    • 3042727183 scopus 로고    scopus 로고
    • Identification and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8- quinone from reactions at physiological pH
    • Balu N, et al. (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 17:827-838.
    • (2004) Chem Res Toxicol , vol.17 , pp. 827-838
    • Balu, N.1
  • 12
    • 0033024560 scopus 로고    scopus 로고
    • Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7-guanine adducts
    • McCoull KD, Rindgen D, Blair IA, Penning TM (1999) Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7-guanine adducts. Chem Res Toxicol 12:237-246.
    • (1999) Chem Res Toxicol , vol.12 , pp. 237-246
    • McCoull, K.D.1    Rindgen, D.2    Blair, I.A.3    Penning, T.M.4
  • 13
    • 0021964203 scopus 로고
    • Prooxidant states and tumor promotion
    • Cerutti PA (1985) Prooxidant states and tumor promotion. Science 227:375-381.
    • (1985) Science , vol.227 , pp. 375-381
    • Cerutti, P.A.1
  • 14
    • 0026592966 scopus 로고
    • 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions
    • Cheng KC, et al. (1992) 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions. J Biol Chem 267:166-172.
    • (1992) J Biol Chem , vol.267 , pp. 166-172
    • Cheng, K.C.1
  • 15
    • 0034068228 scopus 로고    scopus 로고
    • Role of quinones in toxicology
    • Bolton JL, et al. (2000) Role of quinones in toxicology. Chem Res Toxicol 13:135-160.
    • (2000) Chem Res Toxicol , vol.13 , pp. 135-160
    • Bolton, J.L.1
  • 16
    • 0035998283 scopus 로고    scopus 로고
    • Reactive oxygen species generated by PAH o-quinones cause change-in-function mutations in p53
    • Yu D, Berlin JA, Penning TM, Field J (2002) Reactive oxygen species generated by PAH o-quinones cause change-in-function mutations in p53. Chem Res Toxicol 15:832-842.
    • (2002) Chem Res Toxicol , vol.15 , pp. 832-842
    • Yu, D.1    Berlin, J.A.2    Penning, T.M.3    Field, J.4
  • 17
    • 47549087168 scopus 로고    scopus 로고
    • Park J-H, et al. (2008) The pattern of P53 mutation caused by PAH o-quinones is driven by 8-oxo-dGuo formation while the spectrum of mutations is determined by biological selection for dominance. Chem Res Toxicol 21, in press.
    • Park J-H, et al. (2008) The pattern of P53 mutation caused by PAH o-quinones is driven by 8-oxo-dGuo formation while the spectrum of mutations is determined by biological selection for dominance. Chem Res Toxicol 21, in press.
  • 18
    • 13844264435 scopus 로고    scopus 로고
    • Competing roles of cytochrome P450 1A1/1B1 and aldo-keto reductase 1A1 in the metabolic activation of (+/-)-7,8-dihydroxy-7,8-dihydro-benzopyrene in human bronchoalveolar cell extracts
    • Jiang H, Shen YM, Quinn AM, Penning TM (2005) Competing roles of cytochrome P450 1A1/1B1 and aldo-keto reductase 1A1 in the metabolic activation of (+/-)-7,8-dihydroxy-7,8-dihydro-benzopyrene in human bronchoalveolar cell extracts. Chem Res Toxicol 18:365-374.
    • (2005) Chem Res Toxicol , vol.18 , pp. 365-374
    • Jiang, H.1    Shen, Y.M.2    Quinn, A.M.3    Penning, T.M.4
  • 19
    • 31844444754 scopus 로고    scopus 로고
    • 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
    • Jiang H, Vudathala DK, Blair IA, Penning TM (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 19:68-78.
    • (2006) Chem Res Toxicol , vol.19 , pp. 68-78
    • Jiang, H.1    Vudathala, D.K.2    Blair, I.A.3    Penning, T.M.4
  • 20
    • 0037025386 scopus 로고    scopus 로고
    • 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
    • Palackal NT, et al. (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. J Biol Chem 277:24799-24808.
    • (2002) J Biol Chem , vol.277 , pp. 24799-24808
    • Palackal, N.T.1
  • 21
    • 33749055937 scopus 로고    scopus 로고
    • Smoking and cancer-related gene expression in bronchial epithelium and non-small-cell lung cancers
    • Woenckhaus M, et al. (2006) Smoking and cancer-related gene expression in bronchial epithelium and non-small-cell lung cancers. J Pathol 210:192-204.
    • (2006) J Pathol , vol.210 , pp. 192-204
    • Woenckhaus, M.1
  • 22
    • 20144387888 scopus 로고    scopus 로고
    • Overexpression of the aldo-keto reductase family protein AKR1B10 is highly correlated with smokers' non-small cell lung carcinomas
    • Fukumoto S, et al. (2005) Overexpression of the aldo-keto reductase family protein AKR1B10 is highly correlated with smokers' non-small cell lung carcinomas. Clin Cancer Res 11:1776-1785.
    • (2005) Clin Cancer Res , vol.11 , pp. 1776-1785
    • Fukumoto, S.1
  • 23
    • 0031553958 scopus 로고    scopus 로고
    • Validated high-performance liquid chromatography-electrochemical method for determination of glutathione and glutathione disulfide in small tissue samples
    • Lakritz J, Plopper CG, Buckpitt AR (1997) Validated high-performance liquid chromatography-electrochemical method for determination of glutathione and glutathione disulfide in small tissue samples. Anal Biochem 247:63-68.
    • (1997) Anal Biochem , vol.247 , pp. 63-68
    • Lakritz, J.1    Plopper, C.G.2    Buckpitt, A.R.3
  • 24
    • 73049123450 scopus 로고
    • The measurement of pyridine nucleotides by enzymatic cycling
    • Lowry OH, Passoneau JV, Rock MK (1961) The measurement of pyridine nucleotides by enzymatic cycling. J Biol Chem 236:2756-2759.
    • (1961) J Biol Chem , vol.236 , pp. 2756-2759
    • Lowry, O.H.1    Passoneau, J.V.2    Rock, M.K.3
  • 25
    • 11244327638 scopus 로고    scopus 로고
    • Establishing the background level of base oxidation in human lymphocyte DNA: Results of an interlaboratory validation study
    • European Standards Committee on Oxidative DNA Damage
    • European Standards Committee on Oxidative DNA Damage, Gedik CM, Collins A (2005) Establishing the background level of base oxidation in human lymphocyte DNA: Results of an interlaboratory validation study. FASEB J 19:82-84.
    • (2005) FASEB J , vol.19 , pp. 82-84
    • Gedik, C.M.1    Collins, A.2
  • 26
    • 33745107265 scopus 로고    scopus 로고
    • hOGG1 recognizes oxidative damage using the comet assay with greater specificity than FPG or ENDOIII
    • Smith CC, O'Donovan MR, Martin EA (2006) hOGG1 recognizes oxidative damage using the comet assay with greater specificity than FPG or ENDOIII. Mutagenesis 21:185-190.
    • (2006) Mutagenesis , vol.21 , pp. 185-190
    • Smith, C.C.1    O'Donovan, M.R.2    Martin, E.A.3
  • 27
    • 0032531145 scopus 로고    scopus 로고
    • Characterization of the A549 cell line as a type II pulmonary epithelial cell model for drug metabolism
    • Foster KA, et al. (1998) Characterization of the A549 cell line as a type II pulmonary epithelial cell model for drug metabolism. Exp Cell Res 243:359-366.
    • (1998) Exp Cell Res , vol.243 , pp. 359-366
    • Foster, K.A.1
  • 28
    • 0034652743 scopus 로고    scopus 로고
    • Genotoxic polycyclic aromatic hydrocarbon orthoquinones generated by aldo-keto reductases induce CYP1A1 via nuclear translocation of the aryl hydrocarbon receptor
    • Burczynski ME, Penning TM (2000) Genotoxic polycyclic aromatic hydrocarbon orthoquinones generated by aldo-keto reductases induce CYP1A1 via nuclear translocation of the aryl hydrocarbon receptor. Cancer Res 60:908-915.
    • (2000) Cancer Res , vol.60 , pp. 908-915
    • Burczynski, M.E.1    Penning, T.M.2
  • 29
    • 0024437491 scopus 로고
    • Genotoxicity of 1,4-benzoquinone and 1,4-naphthoquinone in relation to effects on glutathione and NAD(P)H levels in V79 cells
    • Ludewig G, Dogra S, Glatt H (1989) Genotoxicity of 1,4-benzoquinone and 1,4-naphthoquinone in relation to effects on glutathione and NAD(P)H levels in V79 cells. Environ Health Perspect 82:223-228.
    • (1989) Environ Health Perspect , vol.82 , pp. 223-228
    • Ludewig, G.1    Dogra, S.2    Glatt, H.3
  • 30
    • 21144438119 scopus 로고    scopus 로고
    • 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
    • Park J-H, et al. (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. Chem Res Toxicol 18:1026-1037.
    • (2005) Chem Res Toxicol , vol.18 , pp. 1026-1037
    • Park, J.-H.1
  • 31
    • 0030703177 scopus 로고    scopus 로고
    • Opposite base-dependent reactions of a human base excision repair enzyme on DNA containing 7,8-dihydro-8-oxoguanine and abasic sites
    • Bjørås M, et al. (1997) Opposite base-dependent reactions of a human base excision repair enzyme on DNA containing 7,8-dihydro-8-oxoguanine and abasic sites. EMBO J 16:6314-6322.
    • (1997) EMBO J , vol.16 , pp. 6314-6322
    • Bjørås, M.1
  • 32
    • 2042438877 scopus 로고
    • Production of oxidative DNA damage during the metabolic activation of benzo[a]pyrene in human mammary epithelial cells correlates with cell killing
    • Leadon SA, Stampfer MR, Bartley J (1988) Production of oxidative DNA damage during the metabolic activation of benzo[a]pyrene in human mammary epithelial cells correlates with cell killing. Proc Natl Acad Sci USA 85:4365-4368.
    • (1988) Proc Natl Acad Sci USA , vol.85 , pp. 4365-4368
    • Leadon, S.A.1    Stampfer, M.R.2    Bartley, J.3
  • 33
    • 0029562365 scopus 로고
    • Coal tar residues produce both DNA adducts and oxidative DNA damage in human mammary epithelial cells
    • Leadon SA, Sumerel J, Minton TA, Tischler A (1995) Coal tar residues produce both DNA adducts and oxidative DNA damage in human mammary epithelial cells. Carcinogenesis 16:3021-3026.
    • (1995) Carcinogenesis , vol.16 , pp. 3021-3026
    • Leadon, S.A.1    Sumerel, J.2    Minton, T.A.3    Tischler, A.4
  • 34
    • 0031586757 scopus 로고    scopus 로고
    • Oxidative stress to DNA, protein, and antioxidant enzymes (superoxide dismutase and catalase) in rats treated with benzo(a)pyrene
    • Kim KB, Lee BM (1997) Oxidative stress to DNA, protein, and antioxidant enzymes (superoxide dismutase and catalase) in rats treated with benzo(a)pyrene. Cancer Lett 113:205-212.
    • (1997) Cancer Lett , vol.113 , pp. 205-212
    • Kim, K.B.1    Lee, B.M.2
  • 35
    • 0032508052 scopus 로고    scopus 로고
    • Mutations in OGG1, a gene involved in the repair of oxidative DNA damage, are found in human lung and kidney tumors
    • Chevillard S, et al. (1998) Mutations in OGG1, a gene involved in the repair of oxidative DNA damage, are found in human lung and kidney tumors. Oncogene 16:3083-3086.
    • (1998) Oncogene , vol.16 , pp. 3083-3086
    • Chevillard, S.1
  • 36
    • 0034672199 scopus 로고    scopus 로고
    • hOGG1 polymorphism and loss of heterozygosity (LOH): Significance for lung cancer susceptibility in a Caucasian population
    • Wikman H, et al. (2000) hOGG1 polymorphism and loss of heterozygosity (LOH): Significance for lung cancer susceptibility in a Caucasian population. Int J Cancer 88:932-937.
    • (2000) Int J Cancer , vol.88 , pp. 932-937
    • Wikman, H.1
  • 37
    • 0033976148 scopus 로고    scopus 로고
    • The effect of hOGG1 and glutathione peroxidase I genotypes and 3p chromosomal loss on 8-hydroxydeoxyguanosine levels in lung cancer
    • Hardie LJ, et al. (2000) The effect of hOGG1 and glutathione peroxidase I genotypes and 3p chromosomal loss on 8-hydroxydeoxyguanosine levels in lung cancer. Carcinogenesis 21:167-172.
    • (2000) Carcinogenesis , vol.21 , pp. 167-172
    • Hardie, L.J.1
  • 38
    • 0042832464 scopus 로고    scopus 로고
    • DNA repair activity for oxidative damage and risk of lung cancer
    • Paz-Elizur T, et al. (2003) DNA repair activity for oxidative damage and risk of lung cancer. J Natl Cancer Inst 95:1312-1319.
    • (2003) J Natl Cancer Inst , vol.95 , pp. 1312-1319
    • Paz-Elizur, T.1
  • 39
    • 0041438479 scopus 로고    scopus 로고
    • Products of oxidative DNA damage and repair as possible biomarkers of susceptibility to lung cancer
    • Gackowski D, et al. (2003) Products of oxidative DNA damage and repair as possible biomarkers of susceptibility to lung cancer. Cancer Res 63:4899-4902.
    • (2003) Cancer Res , vol.63 , pp. 4899-4902
    • Gackowski, D.1
  • 40
    • 4344583242 scopus 로고    scopus 로고
    • Hydroxychavicol modulates benzo-[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase
    • Tang DW, Chang KW, Chi CW, Liu TY (2004) Hydroxychavicol modulates benzo-[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase. Toxicol Lett 152:235-243.
    • (2004) Toxicol Lett , vol.152 , pp. 235-243
    • Tang, D.W.1    Chang, K.W.2    Chi, C.W.3    Liu, T.Y.4
  • 41
    • 1642272391 scopus 로고    scopus 로고
    • Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis
    • Harvey RG, Dai Q, Ran C, Penning TM (2004) Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis. J Org Chem 69:2024-2032.
    • (2004) J Org Chem , vol.69 , pp. 2024-2032
    • Harvey, R.G.1    Dai, Q.2    Ran, C.3    Penning, T.M.4


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