메뉴 건너뛰기




Volumn 21, Issue 3, 2008, Pages 720-725

Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: Naphthalene, styrene, and toluene

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; 4 NITROPHENOL; 6 HYDROXYCHLORZOXAZONE; BENZYL ALCOHOL; CYTOCHROME P450 1A2; CYTOCHROME P450 2A; CYTOCHROME P450 2A13; CYTOCHROME P450 2E1; NAPHTHALENE; NAPHTHOQUINONE; STYRENE; TOBACCO SMOKE; TOLUENE; UNCLASSIFIED DRUG;

EID: 41849093006     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700325f     Document Type: Article
Times cited : (74)

References (47)
  • 2
    • 0025022689 scopus 로고
    • The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes
    • Yamano, S., Tatsuno, J., and Gonzalez, F. J. (1990) The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 29, 1322-1329.
    • (1990) Biochemistry , vol.29 , pp. 1322-1329
    • Yamano, S.1    Tatsuno, J.2    Gonzalez, F.J.3
  • 3
    • 0034665139 scopus 로고    scopus 로고
    • Human cytochrome P450 CYP2A13: Predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • Su, T., Bao, Z., Zhang, Q. Y., Smith, T. J., Hong, J. Y., and Ding, X. (2000) Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 60, 5074-5079.
    • (2000) Cancer Res , vol.60 , pp. 5074-5079
    • Su, T.1    Bao, Z.2    Zhang, Q.Y.3    Smith, T.J.4    Hong, J.Y.5    Ding, X.6
  • 4
    • 13444274285 scopus 로고    scopus 로고
    • Metabolism of nicotine and cotinine by human cytochrome P450 2A13
    • Bao, Z., He, X. Y., Ding, X., Prabhu, S., and Hong, J. Y. (2005) Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab. Dispos. 33, 258-261.
    • (2005) Drug Metab. Dispos , vol.33 , pp. 258-261
    • Bao, Z.1    He, X.Y.2    Ding, X.3    Prabhu, S.4    Hong, J.Y.5
  • 6
    • 0034212519 scopus 로고    scopus 로고
    • Expression and biotransformation enzymes in human fetal olfactory mucosa: Potential roles in developmental toxicity
    • Gu, J., Su, Y., Chen, Q. Y., Zhang, X., and Ding, X. (2000) Expression and biotransformation enzymes in human fetal olfactory mucosa: potential roles in developmental toxicity. Toxicol. Appl. Pharmacol. 165, 158-162.
    • (2000) Toxicol. Appl. Pharmacol , vol.165 , pp. 158-162
    • Gu, J.1    Su, Y.2    Chen, Q.Y.3    Zhang, X.4    Ding, X.5
  • 8
    • 33847387556 scopus 로고    scopus 로고
    • CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin and theophylline
    • Fukami, T., Nakajima, M., Sakai, H., Katoh, M., and Yokoi, T. (2007) CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin and theophylline. Drug Metab. Dispos. 35, 335-339.
    • (2007) Drug Metab. Dispos , vol.35 , pp. 335-339
    • Fukami, T.1    Nakajima, M.2    Sakai, H.3    Katoh, M.4    Yokoi, T.5
  • 10
    • 0026116612 scopus 로고
    • Application of Pseudomonas pulid PpG786 containing P-450 cytochrome monooxygenase for removal of trace naphthalene concentrations
    • Kulisch, G. P., and Vilker, V. L. (1991) Application of Pseudomonas pulid PpG786 containing P-450 cytochrome monooxygenase for removal of trace naphthalene concentrations. Biotechnol. Prog. 7, 93-98.
    • (1991) Biotechnol. Prog , vol.7 , pp. 93-98
    • Kulisch, G.P.1    Vilker, V.L.2
  • 11
    • 0027759768 scopus 로고
    • Retrospective evaluation of the exposure to polycyclic aromatic hydrocarbons: Comparative evaluations with a job exposure matrix and by experts in industrial hygiene
    • Stucker, I., Bouyer, J., Mandereau, L., and Hemon, D. (1993) Retrospective evaluation of the exposure to polycyclic aromatic hydrocarbons: comparative evaluations with a job exposure matrix and by experts in industrial hygiene. Int. J. Epidemiol. 22, 5106-5112.
    • (1993) Int. J. Epidemiol , vol.22 , pp. 5106-5112
    • Stucker, I.1    Bouyer, J.2    Mandereau, L.3    Hemon, D.4
  • 12
    • 0029745142 scopus 로고    scopus 로고
    • Naphthalene-induced oxidative stress in rats and the prospective effects of vitamine E succinate
    • Vuchetich, P. J., Bagchi, D., Bagchi, M., Hassoun, E. A., Tang, L., and Stohs, S. J. (1996) Naphthalene-induced oxidative stress in rats and the prospective effects of vitamine E succinate. Free Radical Biol. Med. 21, 577-590.
    • (1996) Free Radical Biol. Med , vol.21 , pp. 577-590
    • Vuchetich, P.J.1    Bagchi, D.2    Bagchi, M.3    Hassoun, E.A.4    Tang, L.5    Stohs, S.J.6
  • 14
    • 29944447220 scopus 로고    scopus 로고
    • In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes
    • Cho, T. M., Rose, R. L., and Hodgson, E. (2006) In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Drug. Metab. Dispos. 34, 176-183.
    • (2006) Drug. Metab. Dispos , vol.34 , pp. 176-183
    • Cho, T.M.1    Rose, R.L.2    Hodgson, E.3
  • 15
    • 0026057999 scopus 로고
    • Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung
    • Kanekal, S., Plopper, C., Morin, D., and Buckpitt, A. (1991) Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung. J. Pharmacol. Exp. Ther. 256, 391-401.
    • (1991) J. Pharmacol. Exp. Ther , vol.256 , pp. 391-401
    • Kanekal, S.1    Plopper, C.2    Morin, D.3    Buckpitt, A.4
  • 16
    • 0028855791 scopus 로고
    • Relationship of cytochrome P450 activity to Clara cell cytotoxicity. IV. Metabolism of naphthalene and naphthalene oxide in microdissected airways from mice, rats and hamsters
    • Buckpitt, A., Chang, A. M., Weir, A., Van Winkle, L., Duan, X., Philpot, R., and Plopper, C. (1995) Relationship of cytochrome P450 activity to Clara cell cytotoxicity. IV. Metabolism of naphthalene and naphthalene oxide in microdissected airways from mice, rats and hamsters. Mol. Pharmacol. 47, 74-81.
    • (1995) Mol. Pharmacol , vol.47 , pp. 74-81
    • Buckpitt, A.1    Chang, A.M.2    Weir, A.3    Van Winkle, L.4    Duan, X.5    Philpot, R.6    Plopper, C.7
  • 19
    • 0024560505 scopus 로고
    • Review of the toxicology of styrene
    • Bond, J. A. (1989) Review of the toxicology of styrene. CRC Crit. Rev. Toxicol. 19, 227-249.
    • (1989) CRC Crit. Rev. Toxicol , vol.19 , pp. 227-249
    • Bond, J.A.1
  • 20
    • 0025303557 scopus 로고
    • Chronic neurobehavioral effects of toluene
    • Foo, S. C., Jeyaratnam, J., and Koh, D. (1990) Chronic neurobehavioral effects of toluene. Br. J. Ind. Med. 47, 480-484.
    • (1990) Br. J. Ind. Med , vol.47 , pp. 480-484
    • Foo, S.C.1    Jeyaratnam, J.2    Koh, D.3
  • 25
    • 10044244648 scopus 로고    scopus 로고
    • A novel polymorphism of human CYP2A6 gene CYP2A6*17 has an amino acid substitution (V365M) that decreases enzymatic activity in vitro and in vivo
    • Fukami, T., Nakajima, M., Yoshida, R., Tsuchiya, Y., Fujiki, Y., Katoh, M., McLeod, H. L., and Yokoi, T. (2004) A novel polymorphism of human CYP2A6 gene CYP2A6*17 has an amino acid substitution (V365M) that decreases enzymatic activity in vitro and in vivo. Clin. Pharmacol. Ther. 76, 519-527.
    • (2004) Clin. Pharmacol. Ther , vol.76 , pp. 519-527
    • Fukami, T.1    Nakajima, M.2    Yoshida, R.3    Tsuchiya, Y.4    Fujiki, Y.5    Katoh, M.6    McLeod, H.L.7    Yokoi, T.8
  • 26
    • 28144450359 scopus 로고    scopus 로고
    • CYP2A6 and CYP2B6 are involved in nornicotine formation from nicotine in humans: Interindividual differences in these contributions
    • Yamanaka, H., Nakajima, M., Fukami, T., Sakai, H., Nakamura, A., Katoh, M., Takamiya, M., Aoki, Y., and Yokoi, T. (2005) CYP2A6 and CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions. Drug Metab. Dispos. 33, 1811-1818.
    • (2005) Drug Metab. Dispos , vol.33 , pp. 1811-1818
    • Yamanaka, H.1    Nakajima, M.2    Fukami, T.3    Sakai, H.4    Nakamura, A.5    Katoh, M.6    Takamiya, M.7    Aoki, Y.8    Yokoi, T.9
  • 27
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes
    • Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378.
    • (1964) J. Biol. Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 28
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
    • (1976) Anal. Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 29
    • 73649173283 scopus 로고
    • Microsomal triphosphopyridine nucleotide-cytochrome c reductase of liver
    • Williams, C. H., Jr., and Kamin, H. (1962) Microsomal triphosphopyridine nucleotide-cytochrome c reductase of liver. J. Biol. Chem. 237, 587-595.
    • (1962) J. Biol. Chem , vol.237 , pp. 587-595
    • Williams Jr., C.H.1    Kamin, H.2
  • 30
    • 0017088267 scopus 로고
    • Some properties of detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinities chromatography
    • Yasukochi, Y., and Masters, B. S. (1995) Some properties of detergent-solubilized NADPH-cytochrome c (cytochrome P-450) reductase purified by biospecific affinities chromatography. J. Biol. Chem. 251, 5337-5344.
    • (1995) J. Biol. Chem , vol.251 , pp. 5337-5344
    • Yasukochi, Y.1    Masters, B.S.2
  • 31
    • 0030843652 scopus 로고    scopus 로고
    • Drug metabolism by Escherichia coli expressing human cytochromes P450
    • Parikh, A., Gillam, E. M., and Guengerich, F. P. (1997) Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol. 15, 784-788.
    • (1997) Nat. Biotechnol , vol.15 , pp. 784-788
    • Parikh, A.1    Gillam, E.M.2    Guengerich, F.P.3
  • 32
    • 0030894106 scopus 로고    scopus 로고
    • Biotransformation of chlorzoxazone by hepatic microsomes from humans and ten other mammalian species
    • Court, M. H., Von Moltke, L. L., Shader, R. I., and Greenblatt, D. J. (1997) Biotransformation of chlorzoxazone by hepatic microsomes from humans and ten other mammalian species. Biopharm. Drug Dispos. 18, 213-226.
    • (1997) Biopharm. Drug Dispos , vol.18 , pp. 213-226
    • Court, M.H.1    Von Moltke, L.L.2    Shader, R.I.3    Greenblatt, D.J.4
  • 33
    • 17744417087 scopus 로고    scopus 로고
    • The detection of cytochrome P450 2E1 and its catalytic activity in rat testis
    • Jiang, Y., Kuo, C. L., Pernecky, S. J., and Piper, W. N. (1998) The detection of cytochrome P450 2E1 and its catalytic activity in rat testis. Biochem. Biophys. Res. Commun. 246, 578-583.
    • (1998) Biochem. Biophys. Res. Commun , vol.246 , pp. 578-583
    • Jiang, Y.1    Kuo, C.L.2    Pernecky, S.J.3    Piper, W.N.4
  • 34
    • 0038771110 scopus 로고    scopus 로고
    • Predictive value of comparative molecular field analysis modeling of naphthalene inhibition of human CYP2A6 and mouse CYP2A5 enzymes
    • Asikainen, A., Tarhanen, J., Poso, A., Pasanen, M., Alhava, E., and Juvonen, R. O. (2003) Predictive value of comparative molecular field analysis modeling of naphthalene inhibition of human CYP2A6 and mouse CYP2A5 enzymes. Toxicol. in Vitro 17, 449-455.
    • (2003) Toxicol. in Vitro , vol.17 , pp. 449-455
    • Asikainen, A.1    Tarhanen, J.2    Poso, A.3    Pasanen, M.4    Alhava, E.5    Juvonen, R.O.6
  • 35
    • 0347416985 scopus 로고    scopus 로고
    • A recombinant model for assessing the role of GSTM1 in styrene-7,8-oxide toxicity and mutagenecity
    • Shield, A. J., and Sanderson, B. J. (2004) A recombinant model for assessing the role of GSTM1 in styrene-7,8-oxide toxicity and mutagenecity. Toxicology 195, 61-68.
    • (2004) Toxicology , vol.195 , pp. 61-68
    • Shield, A.J.1    Sanderson, B.J.2
  • 36
    • 0037447571 scopus 로고    scopus 로고
    • Individual sensitivity to DNA damage induced by styrene in vitro: Influence of cytochrome P450 epoxide hydrolase and glutathione S-transferase genotypes
    • Laffon, B., Perez-cadahia, B., Pasaro, E., and Mendez, J. (2003) Individual sensitivity to DNA damage induced by styrene in vitro: influence of cytochrome P450 epoxide hydrolase and glutathione S-transferase genotypes. Toxicology 186, 131-141.
    • (2003) Toxicology , vol.186 , pp. 131-141
    • Laffon, B.1    Perez-cadahia, B.2    Pasaro, E.3    Mendez, J.4
  • 37
    • 0026035519 scopus 로고
    • Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects
    • Guengerich, F. P., Kim, D. H., and Iwasaki, M. (1991) Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4, 168-179.
    • (1991) Chem. Res. Toxicol , vol.4 , pp. 168-179
    • Guengerich, F.P.1    Kim, D.H.2    Iwasaki, M.3
  • 39
    • 34347235844 scopus 로고    scopus 로고
    • Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2
    • Sansen, S., Yano, J. K., Reynald, R. L., Schoch, G. A., Griffin, K. J., Stout, C. D., and Johnson, E. F. (2007) Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J. Biol. Chem. 282, 14348-14355.
    • (2007) J. Biol. Chem , vol.282 , pp. 14348-14355
    • Sansen, S.1    Yano, J.K.2    Reynald, R.L.3    Schoch, G.A.4    Griffin, K.J.5    Stout, C.D.6    Johnson, E.F.7
  • 40
    • 33748918311 scopus 로고    scopus 로고
    • CYP2A13 in human respiratory tissues and lung cancers: An immunohistochemical study with a new peptide-specific antibody
    • Zhu, L. R., Thomas, P. E., Lu, G., Reuhl, K. R., Yang, G. Y., Wang, L. D., Wang, S. L., Yang, C. S., He, X. Y., and Hong, J. Y. (2006) CYP2A13 in human respiratory tissues and lung cancers: an immunohistochemical study with a new peptide-specific antibody. Drug Metab. Dispos. 34, 1672-1676.
    • (2006) Drug Metab. Dispos , vol.34 , pp. 1672-1676
    • Zhu, L.R.1    Thomas, P.E.2    Lu, G.3    Reuhl, K.R.4    Yang, G.Y.5    Wang, L.D.6    Wang, S.L.7    Yang, C.S.8    He, X.Y.9    Hong, J.Y.10
  • 41
    • 0030006119 scopus 로고    scopus 로고
    • Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs
    • Shimada, T., Yamazaki, H., Mimura, M., Wakamiya, N., Ueng, Y.-F., Guengerich, F. P., and Inui, Y. (1996) Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs. Drug Metab. Dispos. 24, 515-522.
    • (1996) Drug Metab. Dispos , vol.24 , pp. 515-522
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Wakamiya, N.4    Ueng, Y.-F.5    Guengerich, F.P.6    Inui, Y.7
  • 42
    • 0036070530 scopus 로고    scopus 로고
    • Genetic polymorphisms of the human CYP2A13 gene: Identification of single-nucleotide polymorphisms and functional characterization of an Arg257Cys variant
    • Zhang, X., Su, T., Zhang, Q. Y., Gu, J., Caggana, M., Li, H., and Ding, X. (2002) Genetic polymorphisms of the human CYP2A13 gene: identification of single-nucleotide polymorphisms and functional characterization of an Arg257Cys variant. J. Pharmacol. Exp. Ther. 302, 416-423.
    • (2002) J. Pharmacol. Exp. Ther , vol.302 , pp. 416-423
    • Zhang, X.1    Su, T.2    Zhang, Q.Y.3    Gu, J.4    Caggana, M.5    Li, H.6    Ding, X.7
  • 44
    • 33749608123 scopus 로고    scopus 로고
    • The missense genetic polymorphisms of human CYP2A13: Functional significance in carcinogen activation and identification of a null allelic variant
    • Wang, S. L., He, X. Y., Shen, J., Wang, J. S., and Hong, J. Y. (2006) The missense genetic polymorphisms of human CYP2A13: functional significance in carcinogen activation and identification of a null allelic variant. Toxicol. Sci. 94, 38-45.
    • (2006) Toxicol. Sci , vol.94 , pp. 38-45
    • Wang, S.L.1    He, X.Y.2    Shen, J.3    Wang, J.S.4    Hong, J.Y.5
  • 45
    • 4644227631 scopus 로고    scopus 로고
    • Development of a real-time polymerase chain reaction-based method for the measurement of relative allelic expression and identification of CYP2A13 alleles with decreased expression in human lung
    • Zhang, X., Caggana, M., Cutler, T. L., and Ding, X. (2004) Development of a real-time polymerase chain reaction-based method for the measurement of relative allelic expression and identification of CYP2A13 alleles with decreased expression in human lung. J. Pharmacol. Exp. Ther. 311, 373-381.
    • (2004) J. Pharmacol. Exp. Ther , vol.311 , pp. 373-381
    • Zhang, X.1    Caggana, M.2    Cutler, T.L.3    Ding, X.4
  • 46
    • 0345707570 scopus 로고    scopus 로고
    • Substantial reduction in risk of lung adenocarcinoma associated with genetic polymorphism in CYP2A13, the most activate cytochrome P450 for the metabolic activation of tobacco-specific carcinogen NNK
    • Wang, H., Tan, W., Hao, B., Miao, X., Zhou, G., He, F., and Lin, D. (2003) Substantial reduction in risk of lung adenocarcinoma associated with genetic polymorphism in CYP2A13, the most activate cytochrome P450 for the metabolic activation of tobacco-specific carcinogen NNK. Cancer Res. 63, 8057-8061.
    • (2003) Cancer Res , vol.63 , pp. 8057-8061
    • Wang, H.1    Tan, W.2    Hao, B.3    Miao, X.4    Zhou, G.5    He, F.6    Lin, D.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.