메뉴 건너뛰기




Volumn 22, Issue 3, 2009, Pages 426-432

Preferential glutathione conjugation of a reverse diol epoxide compared to a bay region diol epoxide of phenanthrene in human hepatocytes: Relevance to molecular epidemiology studies of glutathione-s-transferase polymorphisms and cancer

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; ACETYLCYSTEINE DERIVATIVE; ANTIPHENANTHRENE 1,2 DIOL 3,4 EPOXIDE; ANTIPHENANTHRENE 3,4 DIOL 1,2 EPOXIDE; EPOXIDE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; PHENANTHRENE DERIVATIVE; PHENANTHRENEQUINONE; UNCLASSIFIED DRUG;

EID: 65949121359     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800315m     Document Type: Article
Times cited : (13)

References (34)
  • 1
    • 84967546681 scopus 로고    scopus 로고
    • Metabolic activation and detoxification of polycyclic aromatic hydrocarbons
    • Luich, A., Ed. Imperial College Press, London
    • Luch, A. and Baird, W. M. (2005) Metabolic Activation and Detoxification of Polycyclic Aromatic Hydrocarbons. In The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons. (Luich, A., Ed.) pp 19-96, Imperial College Press, London.
    • (2005) The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons , pp. 19-96
    • Luch, A.1    Baird, W.M.2
  • 3
    • 0020431144 scopus 로고
    • Induction of microsomal enzymes for foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A. Clowes Memorial Lecture
    • Conney, A. H. (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. (Pubitemid 13223122)
    • (1982) Cancer Research , vol.42 , Issue.12 , pp. 4875-4917
    • Conney, A.H.1
  • 4
    • 0000751859 scopus 로고
    • The metabolism and activation of benzo[a]pyrene
    • Cooper, C. S., Grover, P. L., and Sims, P. (1983) The metabolism and activation of benzo[a]pyrene. Prog. Drug Metab. 7, 295-396.
    • (1983) Prog. Drug Metab. , vol.7 , pp. 295-396
    • Cooper, C.S.1    Grover, P.L.2    Sims, P.3
  • 5
    • 0021007163 scopus 로고
    • Polynuclear aromatic Compounds, Part 1. chemical, environmental and experimental data
    • International Agency for Research on Cancer, IARC, Lyon, France
    • International Agency for Research on Cancer (1983) Polynuclear Aromatic Compounds, Part 1. Chemical, Environmental and Experimental Data. In IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 32, pp 419-430, IARC, Lyon, France.
    • (1983) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans , vol.32 , pp. 419-430
  • 6
    • 0003173565 scopus 로고
    • 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, IARC, Lyon, France.
    • International Agency for Research on Cancer (1984) Polynuclear Aromatic Compounds, Part 3. Industrial Exposures in Aluminum Production, Coal Gasification, Coke Production, and Iron and Steel Founding. In IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 34, pp 65-131, IARC, Lyon, France.
    • (1984) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans , vol.34 , pp. 65-131
  • 7
    • 0021951738 scopus 로고
    • Polynuclear Aromatic Compounds, Part 4. Bitumens, Coal-Tars and Derived Products, Shale Oils and Soots
    • International Agency for Research on Cancer, IARC, Lyon, France.
    • International Agency for Research on Cancer (1985) Polynuclear Aromatic Compounds, Part 4. Bitumens, Coal-Tars and Derived Products, Shale Oils and Soots. In IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 35, pp 83-241, IARC, Lyon, France.
    • (1985) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans , vol.35 , pp. 83-241
  • 8
    • 0142228320 scopus 로고    scopus 로고
    • Tobacco carcinogens, their biomarkers and tobacco-induced cancer
    • Hecht, S. S. (2003) Tobacco carcinogens, their biomarkers, and tobacco-induced cancer. Nature Rev. Cancer 3, 733-744. (Pubitemid 37328812)
    • (2003) Nature Reviews Cancer , vol.3 , Issue.10 , pp. 733-744
    • Hecht, S.S.1
  • 9
    • 0036174215 scopus 로고    scopus 로고
    • Glutathione conjugation and DNA adduct formation of dibenzo[a, l]pyrene and benzo[a]pyrene diol epoxides in V79 cells stably expressing different human glutathione transferases
    • DOI 10.1021/tx015546t
    • Sundberg, K., Dreij, K., Seidel, A., and Jernstrom, B. (2002) Glutathione conjugation and DNA adduct formation of dibenzo[ a, l]pyrene and benzo[a]pyrene diol epoxides in V79 cells stably expressing different human glutathione transferases. Chem. Res. Toxicol. 15, 170-179. (Pubitemid 34163797)
    • (2002) Chemical Research in Toxicology , vol.15 , Issue.2 , pp. 170-179
    • Sundberg, K.1    Dreij, K.2    Seidel, A.3    Jernstrom, B.4
  • 11
    • 0039893835 scopus 로고    scopus 로고
    • Expression of human glutathione transferases in V79 cells and the effect on DNA adduct-formation of diol epoxides derived from polycyclic aromatic hydrocarbons
    • PII S0009279700002167
    • Sundberg, K., Dreij, K., Berntsen, S., Seidel, A., and Jernstrom, B. (2001) Expression of human glutathione transferases in V79 cells and the effect on DNA adduct-formation of diol epoxides derived from polycyclic aromatic hydrocarbons. Chem.-Biol. Interact. 133, 91-94. (Pubitemid 33591355)
    • (2001) Chemico-Biological Interactions , vol.133 , Issue.1-3 , pp. 95-97
    • Sundberg, K.1    Dreij, K.2    Berntsen, S.3    Seidel, A.4    Jernstrom, B.5
  • 12
    • 0031878866 scopus 로고    scopus 로고
    • Differences in the catalytic efficiencies of allelic variants of glutathione transferase P1-1 towards carcinogenic diol epoxides of polycyclic aromatic hydrocarbons
    • DOI 10.1093/carcin/19.3.433
    • Sundberg, K., Johansson, A. S., Stenberg, G., Widersten, M., Seidel, A., Mannervik, B., and Jernstrom, B. (1998) Differences in the catalytic efficiencies of allelic variants of glutathione transferase P1-1 towards carcinogenic diol epoxides of polycyclic aromatic hydrocarbons. Carcinogenesis 19, 433-436. (Pubitemid 28375445)
    • (1998) Carcinogenesis , vol.19 , Issue.3 , pp. 433-436
    • Sundberg, K.1    Johansson, A.-S.2    Stenberg, G.3    Widersten, M.4    Seidel, A.5    Mannervik, B.6    Jernstrom, B.7
  • 13
    • 0030822939 scopus 로고    scopus 로고
    • Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferases M1-1 and P1-1
    • DOI 10.1021/tx970099w
    • Sundberg, K., Widersten, M., Seidel, A., Mannervik, B., and Jernstrom, B. (1997) Glutathione conjugation of bay-and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferase M1-1 and P1-1. Chem. Res. Toxicol. 10, 1221-1227. (Pubitemid 27524826)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.11 , pp. 1221-1227
    • Sundberg, K.1    Widersten, M.2    Seidel, A.3    Mannervik, B.4    Jernstrom, B.5
  • 19
    • 0019516619 scopus 로고
    • Metabolism of chrysene and phenanthrene to bay-region diol epoxides by rat liver enzymes
    • Nordquist, M., Thakker, D. R., Vyas, K. P., Yagi, H., Levin, W., Ryan, D. E., and Thomas, P. E. (1981) Metabolism of chrysene and phenanthrene to bay-region diol epoxides by rat liver enzymes. Mol. Pharmacol. 19, 168-178. (Pubitemid 11104888)
    • (1981) Molecular Pharmacology , vol.19 , Issue.1 , pp. 168-178
    • Nordqvist, M.1    Thakker, D.R.2    Vyas, K.P.3
  • 20
    • 0001488917 scopus 로고
    • Polycyclic aromatic hydrocarbons: Metabolic activation to ultimate carcinogens
    • Anders, M. W., Ed., Academic Press, Inc., New York.
    • Thakker, D. R., Yagi, H., Levin, W., Wood, A. W., Conney, A. H., and Jerina, D. M. (1985) Polycyclic Aromatic Hydrocarbons: Metabolic Activation to Ultimate Carcinogens. In Bioactivation of Foreign Compounds. (Anders, M. W., Ed.), pp177-242, Academic Press, Inc., New York.
    • (1985) Bioactivation of Foreign Compounds , pp. 177-242
    • Thakker, D.R.1    Yagi, H.2    Levin, W.3    Wood, A.W.4    Conney, A.H.5    Jerina, D.M.6
  • 21
    • 0028085833 scopus 로고
    • Regio- and stereo-selective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450
    • DOI 10.1016/0304-3835(94)90334-4
    • Shou, M., Korzekwa, K. R., Krausz, K. W., Crespi, C. L., Gonzalez, F. J., and Gelboin, H. V. (1994) Regio-and stereo-selective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450. Cancer Lett. 83, 305-313. (Pubitemid 24253553)
    • (1994) Cancer Letters , vol.83 , Issue.1-2 , pp. 305-313
    • Shou, M.1    Korzekwa, K.R.2    Krausz, K.W.3    Crespi, C.L.4    Gonzalez, F.J.5    Gelboin, H.V.6
  • 22
    • 30344433749 scopus 로고    scopus 로고
    • Longitudinal study of urinary phenanthrene metabolite ratios: Effect of smoking on the diol epoxide pathway
    • DOI 10.1158/1055-9965.EPI-05-0396
    • Hecht, S. S., Chen, M., Yoder, A., Jensen, J., Hatsukami, D., Le, C., and Carmella, S. G. (2005) Longitudinal study of urinary phenanthrene metabolite ratios: effect of smoking on the diol epoxide pathway. Cancer Epidemiol. Biomarkers Prev. 14, 2969-2974. (Pubitemid 43068832)
    • (2005) Cancer Epidemiology Biomarkers and Prevention , vol.14 , Issue.12 , pp. 2969-2974
    • Hecht, S.S.1    Chen, M.2    Yoder, A.3    Jensen, J.4    Hatsukami, D.5    Le, C.6    Carmella, S.G.7
  • 23
    • 0346732941 scopus 로고    scopus 로고
    • r-1, t-2, 3, c-4-Tetrahydroxy-1, 2, 3, 4-tetrahydrophenanthrene in Human Urine: A Potential Biomarker for Assessing Polycyclic Aromatic Hydrocarbon Metabolic Activation
    • Hecht, S. S., Chen, M., Yagi, H., Jerina, D. M., and Carmella, S. G. (2003) r-1, t-2, 3, c-4-Tetrahydroxy-1, 2, 3, 4-tetrahydrophenanthrene in human urine: a potential biomarker for assessing polycyclic aromatic hydrocarbon metabolic activation. Cancer Epidemiol. Biomarkers Prev. 12, 1501-1508. (Pubitemid 38031755)
    • (2003) Cancer Epidemiology Biomarkers and Prevention , vol.12 , Issue.12 , pp. 1501-1508
    • Hecht, S.S.1    Chen, M.2    Yagi, H.3    Jerina, D.M.4    Carmella, S.G.5
  • 24
    • 47249132099 scopus 로고    scopus 로고
    • Analysis of phenanthrene diol epoxide mercapturic acid detoxification products in human urine: Relevance to molecular epidemiology studies of glutathione-S-transferase polymorphisms
    • Hecht, S. S., Villalta, P. W., and Hochalter, J. B. (2008) Analysis of phenanthrene diol epoxide mercapturic acid detoxification products in human urine: relevance to molecular epidemiology studies of glutathione-S-transferase polymorphisms. Carcinogenesis 29, 937-943.
    • (2008) Carcinogenesis , vol.29 , pp. 937-943
    • Hecht, S.S.1    Villalta, P.W.2    Hochalter, J.B.3
  • 25
    • 0016275313 scopus 로고
    • Glutathione S-transferases. The first enzymatic step in mercapturic acid formation
    • Habig, W. H., Pabst, M. J., and Jakoby, W. B. (1974) Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J. Biol. Chem. 249, 7130-7139.
    • (1974) J. Biol. Chem. , vol.249 , pp. 7130-7139
    • Habig, W.H.1    Pabst, M.J.2    Jakoby, W.B.3
  • 26
    • 33748041085 scopus 로고    scopus 로고
    • Combined analysis of r-1, t-2, 3, c-4-tetrahydroxy-1, 2, 3, 4- tetrahydrophenanthrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' plasma
    • DOI 10.1158/1055-9965.EPI-06-0199
    • Carmella, S. G., Yoder, A., and Hecht, S. S. (2006) Combined analysis of r-1, t-2, 3c-4-tetrahydroxy-1, 2, 3, 4-tetrahydrophenanthrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' plasma. Cancer Epidemiol. Biomarkers PreV 15, 1490-1494. (Pubitemid 44299321)
    • (2006) Cancer Epidemiology Biomarkers and Prevention , vol.15 , Issue.8 , pp. 1490-1494
    • Carmella, S.G.1    Yoder, A.2    Hecht, S.S.3
  • 27
    • 34247352068 scopus 로고    scopus 로고
    • Glutathione transferases in hepatocyte-like cells derived from human embryonic stem cells
    • DOI 10.1016/j.tiv.2007.01.021, PII S0887233307000422
    • Soderdahl, T., Kuppers-Munther, B., Heins, N., Edsbagge, J., Bjorquist, P., Cotgreave, I., and Jernstrom, B. (2007) Glutathione transferases in hepatocyte-like cells derived from human embryonic stem cells. Toxicol. in Vitro 21, 929-937. (Pubitemid 46628908)
    • (2007) Toxicology in Vitro , vol.21 , Issue.5 , pp. 929-937
    • Soderdahl, T.1    Kuppers-Munther, B.2    Heins, N.3    Edsbagge, J.4    Bjorquist, P.5    Cotgreave, I.6    Jernstrom, B.7
  • 28
    • 0025268190 scopus 로고
    • Selectivity of rat and human glutathione S-transferases in activation of ethylene dibromide by glutathione conjugation and DNA binding and induction of unscheduled DNA synthesis in human hepatocytes
    • Cmarik, J. L., Inskeep, P. B., Meredith, M. J., Meyer, D. J., Ketterer, B., and Guengerich, F. P. (1990) Selectivity of rat and human glutathione S-transferases in activation of ethylene dibromide by glutathione conjugation and DNA binding and induction of unscheduled DNA synthesis in human hepatocytes. Cancer Res. 50, 2747-2752. (Pubitemid 20150216)
    • (1990) Cancer Research , vol.50 , Issue.9 , pp. 2747-2752
    • Cmarik, J.L.1    Inskeep, P.B.2    Meredith, M.J.3    Meyer, D.J.4    Ketterer, B.5    Guengerich, F.P.6
  • 29
    • 0031910343 scopus 로고    scopus 로고
    • Human hepatocyte growth factor down-regulates the expression of cytochrome P450 isozymes in human hepatocytes in primary culture
    • Donato, M. T., Gomez-Lechon, M. J., Jover, R., Nakamura, T., and Castell, J. V. (1998) Human hepatocyte growth factor down-regulates the expression of cytochrome P450 isozymes in human hepatocytes in primary culture. J. Pharmacol. Exp. Ther. 284, 760-767. (Pubitemid 28086669)
    • (1998) Journal of Pharmacology and Experimental Therapeutics , vol.284 , Issue.2 , pp. 760-767
    • Donato, M.T.1    Gomez-Lechon, J.2    Jover, R.3    Nakamura, T.4    Castell, J.V.5
  • 31
    • 0032869796 scopus 로고    scopus 로고
    • Profile of urinary phenanthrene metabolites in smokers and non-smokers
    • DOI 10.1080/135475099230705
    • Jacob, J., Grimmer, G., and Dettbarn, G. (1999) Profile of urinary phenanthrene metabolites in smokers and non-smokers. Biomarkers 4, 319-327. (Pubitemid 29482957)
    • (1999) Biomarkers , vol.4 , Issue.5 , pp. 319-327
    • Jacob, J.1    Grimmer, G.2    Dettbarn, G.3
  • 33
    • 0018630511 scopus 로고
    • Tumorigenicity of bay-region expoxides and other derivatives of chrysene and phenanthrene in newborn mice
    • Buening, M. K., Levin, W., Karle, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. (1979) Tumorigenicity of bay-region epoxides and other derivatives of chrysene and phenanthrene in newborn mice. Cancer Res. 39, 5063-5068. (Pubitemid 10163116)
    • (1979) Cancer Research , vol.39 , Issue.12 , pp. 5063-5068
    • Buening, M.K.1    Levin, W.2    Karle, J.M.3
  • 34
    • 0018564935 scopus 로고
    • Mutagenicity and tumorigenicity of phenanthrene and chrysene epoxides and diol epoxides
    • Wood, A. W., Chang, R. L., Levin, W., Ryan, D. E., Thomas, P. E., Mah, H. D., Karle, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. (1979) Mutagenicity and tumorigenicity of phenanthrene and chrysene epoxides and diol epoxides. Cancer Res. 39, 4069-4077. (Pubitemid 10189137)
    • (1979) Cancer Research , vol.39 , Issue.10 , pp. 4069-4077
    • Wood, A.W.1    Chang, R.L.2    Levin, W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.