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Volumn 17, Issue 7, 1996, Pages 1491-1498

Glutathione S-transferase A1-1-catalysed conjugation of bay and fjord region diol epoxides of polycyclic aromatic hydrocarbons with glutathione

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE; CARCINOGEN; CHRYSENE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; ISOENZYME; POLYCYCLIC AROMATIC HYDROCARBON;

EID: 0029956983     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.7.1491     Document Type: Article
Times cited : (82)

References (57)
  • 1
    • 0016217298 scopus 로고
    • Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis
    • Sims, P. and Grover, P.L. (1974) Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis. Adv. Cancer Res., 20, 165-275.
    • (1974) Adv. Cancer Res. , vol.20 , pp. 165-275
    • Sims, P.1    Grover, P.L.2
  • 2
    • 0001488917 scopus 로고
    • Polycyclic aromatic hydrocarbons: Metabolic activation to ultimate carcinogens
    • Anders, M.W. (ed.). Academic Press, New York, NY
    • 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 Anders, M.W. (ed.), Bioactivation of Foreign Compounds. Academic Press, New York, NY, pp. 177-242.
    • (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
  • 3
    • 0022267025 scopus 로고
    • Polycyclic aromatic hydrocarbon carcinogenesis: An introduction
    • Harvey, R.G. (ed.), ACS Symposium Series 283. American Chemical Society, Washington, DC
    • Dipple, A. (1985) Polycyclic aromatic hydrocarbon carcinogenesis: an introduction. In Harvey, R.G. (ed.), Polycyclic Hydrocarbons and Carcinogenesis, ACS Symposium Series 283. American Chemical Society, Washington, DC, pp. 1-17.
    • (1985) Polycyclic Hydrocarbons and Carcinogenesis , pp. 1-17
    • Dipple, A.1
  • 4
    • 0025941641 scopus 로고
    • Witmer, C.M., Snyder, R., Jollow, D.J., Kalf, G.S., Kocsis, J.J. and Sipes, I.G. (eds). Plenum Press, New York, NY
    • Jerina, D.M., Chadha, A., Cheh, A.M., Schurdak, M.E., Wood, A.W. and Sayer, J.M. (1991) In Witmer, C.M., Snyder, R., Jollow, D.J., Kalf, G.S., Kocsis, J.J. and Sipes, I.G. (eds), Biological Reactive Intermediates. Plenum Press, New York, NY, pp. 533-553.
    • (1991) Biological Reactive Intermediates , pp. 533-553
    • Jerina, D.M.1    Chadha, A.2    Cheh, A.M.3    Schurdak, M.E.4    Wood, A.W.5    Sayer, J.M.6
  • 6
    • 0021287601 scopus 로고
    • Mutagenicity of the enantiomers of the diastereomeric bay region benzo[c]phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells
    • Wood, A.W., Chang, R.L., Levin, W., Thakker, D.R., Yagi, H., Sayer, J.M., Jerina, D.M. and Conney, A.H. (1984) Mutagenicity of the enantiomers of the diastereomeric bay region benzo[c]phenanthrene 3,4-diol-1,2-epoxides in bacterial and mammalian cells. Cancer Res, 44, 2320-2324.
    • (1984) Cancer Res , vol.44 , pp. 2320-2324
    • Wood, A.W.1    Chang, R.L.2    Levin, W.3    Thakker, D.R.4    Yagi, H.5    Sayer, J.M.6    Jerina, D.M.7    Conney, A.H.8
  • 7
    • 0022607674 scopus 로고
    • Tumorigenicity of optical isomers of the diastereomeric bay region 3,4-diol-1,2-epoxides of benzo[c]phenanthrene in murine tumor models
    • Levin, W., Chang, R.L., Wood, A.W., Thakker, D.R., Yagi, H., Jerina, D.M. and Conney, A.H. (1986) Tumorigenicity of optical isomers of the diastereomeric bay region 3,4-diol-1,2-epoxides of benzo[c]phenanthrene in murine tumor models. Cancer Res., 46, 2257-2261.
    • (1986) Cancer Res. , vol.46 , pp. 2257-2261
    • Levin, W.1    Chang, R.L.2    Wood, A.W.3    Thakker, D.R.4    Yagi, H.5    Jerina, D.M.6    Conney, A.H.7
  • 8
    • 0025729033 scopus 로고
    • Fjord- and bay-region diol epoxides investigated for stability. SOS induction in Escherichia coli, and mutagenicity in Salmonella typhimurium and mammalian cells
    • Glatt, H., Piée, A., Pauly, K., Steinbrecher, T., Schrode, R., Oesch, F. and Seidel, A. (1991) Fjord- and bay-region diol epoxides investigated for stability. SOS induction in Escherichia coli, and mutagenicity in Salmonella typhimurium and mammalian cells. Cancer Res., 51, 1659-1667.
    • (1991) Cancer Res. , vol.51 , pp. 1659-1667
    • Glatt, H.1    Piée, A.2    Pauly, K.3    Steinbrecher, T.4    Schrode, R.5    Oesch, F.6    Seidel, A.7
  • 9
    • 0027959934 scopus 로고
    • Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides
    • Gill, H.S., Kole, P.L., Wiley, J.C. Li, K.-M., Higginbotham, S., Rogan, E.G. and Cavalieri, E.L. (1994) Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides. Carcinogenesis, 15, 2455-2460.
    • (1994) Carcinogenesis , vol.15 , pp. 2455-2460
    • Gill, H.S.1    Kole, P.L.2    Wiley, J.C.3    Li, K.-M.4    Higginbotham, S.5    Rogan, E.G.6    Cavalieri, E.L.7
  • 10
    • 0028061909 scopus 로고
    • Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene
    • Luch, A., Glatt, H., Platt, K.L., Oesch, F. and Seidel, A. (1994) Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene. Carcinogenesis, 15, 2507-2516.
    • (1994) Carcinogenesis , vol.15 , pp. 2507-2516
    • Luch, A.1    Glatt, H.2    Platt, K.L.3    Oesch, F.4    Seidel, A.5
  • 11
    • 0025948227 scopus 로고
    • Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord- and bay-region diol epoxides of polycyclic aromatic hydrocarbons
    • Phillips, D.H., Hewer, A., Seidel, A., Steinbrecher, T., Schrode, R., Oesch, F. and Glatt, H. (1991) Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord- and bay-region diol epoxides of polycyclic aromatic hydrocarbons. Chem.-Biol. Interactions, 80, 177-186.
    • (1991) Chem.-Biol. Interactions , vol.80 , pp. 177-186
    • Phillips, D.H.1    Hewer, A.2    Seidel, A.3    Steinbrecher, T.4    Schrode, R.5    Oesch, F.6    Glatt, H.7
  • 12
    • 0029142955 scopus 로고
    • Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene, and dibenzo[a,l]pyrene
    • Amin, S., Krzeminski, J., Rivenson, A., Kurtzke, C., Hecht, S.S. and El-Bayoumy, K. (1995) Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene, and dibenzo[a,l]pyrene. Carcinogenesis, 16, 1971-1974.
    • (1995) Carcinogenesis , vol.16 , pp. 1971-1974
    • Amin, S.1    Krzeminski, J.2    Rivenson, A.3    Kurtzke, C.4    Hecht, S.S.5    El-Bayoumy, K.6
  • 13
    • 0029142955 scopus 로고
    • Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene, and dibenzo[a,l]pyrene
    • Amin, S., Desai, D., Dai, W., Kurtzke, C., Harvey, R.G. and Hecht, S.S. (1995) Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene, and dibenzo[a,l]pyrene. Carcinogenesis, 16, 2813-2817.
    • (1995) Carcinogenesis , vol.16 , pp. 2813-2817
    • Amin, S.1    Desai, D.2    Dai, W.3    Kurtzke, C.4    Harvey, R.G.5    Hecht, S.S.6
  • 14
    • 0021943506 scopus 로고
    • Glutathione conjugation of the carcinogenic and mutagenic electrophile (±)-7β,8α-dihydroxy-9α, 10α-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene catalyzed by purified rat liver glutathione transferases
    • Jernström, B., Martinez, M., Meyer, D.J. and Ketterer, B. (1985) Glutathione conjugation of the carcinogenic and mutagenic electrophile (±)-7β,8α-dihydroxy-9α, 10α-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene catalyzed by purified rat liver glutathione transferases. Carcinogenesis, 6, 37-47.
    • (1985) Carcinogenesis , vol.6 , pp. 37-47
    • Jernström, B.1    Martinez, M.2    Meyer, D.J.3    Ketterer, B.4
  • 15
    • 0022991461 scopus 로고
    • Glutathione transferases in rat lung: The presence of transferase 7-7, highly efficient in the conjugation of glutathione with the carcinogenic (+)-7β,8α-dihydroxy-9α,10α-oxy-7,8,9,10- tetrahydrobenzo[a]pyrene
    • Robertson, I.G., Jenssen, H., Mannervik, B. and Jernström, B. (1986) Glutathione transferases in rat lung: the presence of transferase 7-7, highly efficient in the conjugation of glutathione with the carcinogenic (+)-7β,8α-dihydroxy-9α,10α-oxy-7,8,9,10- tetrahydrobenzo[a]pyrene. Carcinogenesis, 7, 295-299.
    • (1986) Carcinogenesis , vol.7 , pp. 295-299
    • Robertson, I.G.1    Jenssen, H.2    Mannervik, B.3    Jernström, B.4
  • 16
    • 0022606742 scopus 로고
    • Differences in stereoselectivity and catalytic efficiency of three human glutathione transferases in the conjugation of glutathione with 7β,8ct-dihydroxy-9a,10a-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene
    • Robertson, I.G., Guthenberg, C., Mannervik, B. and Jernström, B. (1986) Differences in stereoselectivity and catalytic efficiency of three human glutathione transferases in the conjugation of glutathione with 7β,8ct-dihydroxy-9a,10a-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Cancer Res., 46, 2220-2224.
    • (1986) Cancer Res. , vol.46 , pp. 2220-2224
    • Robertson, I.G.1    Guthenberg, C.2    Mannervik, B.3    Jernström, B.4
  • 17
    • 0022796435 scopus 로고
    • The enzymatic conjugation of glutathione with bay-region diol epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene
    • Robertson, I.G. and Jernström, B. (1986) The enzymatic conjugation of glutathione with bay-region diol epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene. Carcinogenesis, 7, 1633-1636.
    • (1986) Carcinogenesis , vol.7 , pp. 1633-1636
    • Robertson, I.G.1    Jernström, B.2
  • 18
    • 0024458426 scopus 로고
    • Effects of glutathione transferase activity on benzo[a]pyrene 7,8-dihydrodiol metabolism and mutagenesis studied in a mammalian cell co-cultivation assay
    • Romert, L., Dock, L., Jenssen, D. and Jernström, B. (1989) Effects of glutathione transferase activity on benzo[a]pyrene 7,8-dihydrodiol metabolism and mutagenesis studied in a mammalian cell co-cultivation assay. Carcinogenesis, 10, 1701-1707.
    • (1989) Carcinogenesis , vol.10 , pp. 1701-1707
    • Romert, L.1    Dock, L.2    Jenssen, D.3    Jernström, B.4
  • 20
    • 0026667334 scopus 로고
    • Glutathione conjugation of trans-3,4-dihydroxy 1,2-epoxy 1,2,3.4-tetrahydrobenzo[c]phenanthrene isomers by human glutathione transferases
    • Jernström, B., Seidel, A., Funk, M., Oesch, F. and Mannervik, B. (1992) Glutathione conjugation of trans-3,4-dihydroxy 1,2-epoxy 1,2,3.4-tetrahydrobenzo[c]phenanthrene isomers by human glutathione transferases. Carcinogenesis, 13, 1549-1555
    • (1992) Carcinogenesis , vol.13 , pp. 1549-1555
    • Jernström, B.1    Seidel, A.2    Funk, M.3    Oesch, F.4    Mannervik, B.5
  • 22
    • 0012947371 scopus 로고
    • Synthesis of dihydrodiols from chrysene and dibenz[a,h]anthracene
    • Karle, J.M., Mah, H.D., Jerina, D.M. and Yagi, H. (1977) Synthesis of dihydrodiols from chrysene and dibenz[a,h]anthracene. Tetrahedron Lett., 4021-4024.
    • (1977) Tetrahedron Lett. , pp. 4021-4024
    • Karle, J.M.1    Mah, H.D.2    Jerina, D.M.3    Yagi, H.4
  • 23
    • 0000547545 scopus 로고
    • Synthesis of the enantiomeric bay-region diol epoxides of benz[a]-anthracene and chrysene
    • Yagi, H., Vyas, K.P., Tada, M., Thakker, D.R. and Jerina, D.M. (1982) Synthesis of the enantiomeric bay-region diol epoxides of benz[a]-anthracene and chrysene. J. Org. Chem., 47, 1110-1117.
    • (1982) J. Org. Chem. , vol.47 , pp. 1110-1117
    • Yagi, H.1    Vyas, K.P.2    Tada, M.3    Thakker, D.R.4    Jerina, D.M.5
  • 24
    • 0041441522 scopus 로고
    • Synthesis of non-K-region ortho quinones of polycyclic aromatic hydrocarbons from cyclic ketones
    • Platt, K.L. and Oesch, F. (1982) Synthesis of non-K-region ortho quinones of polycyclic aromatic hydrocarbons from cyclic ketones. Tetrahedron Lett., ??, 163-166.
    • (1982) Tetrahedron Lett. , pp. 163-166
    • Platt, K.L.1    Oesch, F.2
  • 25
    • 33845551079 scopus 로고
    • Efficient synthesis of non-K-region trans-dihydro diols of polycyclic aromatic hydrocarbons from o-quinones and catechols
    • Platt, K.L. and Oesch, F. (1983) Efficient synthesis of non-K-region trans-dihydro diols of polycyclic aromatic hydrocarbons from o-quinones and catechols. J. Org. Chem., 48, 265-268.
    • (1983) J. Org. Chem. , vol.48 , pp. 265-268
    • Platt, K.L.1    Oesch, F.2
  • 26
    • 0001540204 scopus 로고
    • Synthesis of the dihydrodiol and diol epoxide metabolites of chrysene and 5-methylchrysene
    • Harvey, R.G., Pataki, J. and Lee, H. (1986) Synthesis of the dihydrodiol and diol epoxide metabolites of chrysene and 5-methylchrysene. J. Org. Chem., 51, 1407-1412.
    • (1986) J. Org. Chem. , vol.51 , pp. 1407-1412
    • Harvey, R.G.1    Pataki, J.2    Lee, H.3
  • 27
    • 0006489156 scopus 로고
    • Activated metabolites of chrysene: Synthesis of 9-hydroxychrysene-1,2-diol and the corresponding bay-region syn- and anti-triol-epoxides
    • Cooke, M., Loening, K. and Merritt, J. (eds). Battelle Press, Columbus, OH
    • Seidel, A., Bochnitschek, W., Glatt, H.R., Hodgson, R.M., Grover, P.L. and Oesch, F. (1991) Activated metabolites of chrysene: synthesis of 9-hydroxychrysene-1,2-diol and the corresponding bay-region syn- and anti-triol-epoxides. In Cooke, M., Loening, K. and Merritt, J. (eds), Polynuclear Aromatic Hydrocarbons: Measurements, Means and Metabolism. Battelle Press, Columbus, OH, pp. 801-818.
    • (1991) Polynuclear Aromatic Hydrocarbons: Measurements, Means and Metabolism , pp. 801-818
    • Seidel, A.1    Bochnitschek, W.2    Glatt, H.R.3    Hodgson, R.M.4    Grover, P.L.5    Oesch, F.6
  • 28
    • 0016767875 scopus 로고
    • Metabolites of polycyclic aromatic hydrocarbons. II. Synthesis of 7,8-dihydro-benzo[a]pyrene-7,8-diol and 7,8-dihydrobenzo[a]pyrene-7,8-epoxide
    • McCaustland, D.J. and Engel, J.F. (1975) Metabolites of polycyclic aromatic hydrocarbons. II. Synthesis of 7,8-dihydro-benzo[a]pyrene-7,8-diol and 7,8-dihydrobenzo[a]pyrene-7,8-epoxide. Tetrahedron Lett., 2549-2552.
    • (1975) Tetrahedron Lett. , pp. 2549-2552
    • McCaustland, D.J.1    Engel, J.F.2
  • 29
    • 0017382226 scopus 로고
    • Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene
    • Yagi, H., Thakker, D.M., Hernandez, O., Koreeda, M. and Jerina, D.M. (1977) Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene. J. Am. Chem. Soc., 99, 1604-1611.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 1604-1611
    • Yagi, H.1    Thakker, D.M.2    Hernandez, O.3    Koreeda, M.4    Jerina, D.M.5
  • 30
    • 0017368174 scopus 로고
    • Absolute stereochemistry of the highly mutagenic 7,8-diol 9,10-epoxide derived from the potent carcinogen trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene
    • Yagi, H., Akagi, H., Thakker, D.R., Mah, H.D., Koreeda, M. and Jerina, D.M. (1977) Absolute stereochemistry of the highly mutagenic 7,8-diol 9,10-epoxide derived from the potent carcinogen trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene. J. Am. Chem. Soc., 99, 2358-2359.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 2358-2359
    • Yagi, H.1    Akagi, H.2    Thakker, D.R.3    Mah, H.D.4    Koreeda, M.5    Jerina, D.M.6
  • 31
    • 0001852211 scopus 로고
    • Synthesis of the diols and diolepoxides of carcinogenic hydrocarbons
    • Fu, P.P. and Harvey, R.G. (1977) Synthesis of the diols and diolepoxides of carcinogenic hydrocarbons. Tetrahedron Lett., 2059-2062.
    • (1977) Tetrahedron Lett. , pp. 2059-2062
    • Fu, P.P.1    Harvey, R.G.2
  • 32
    • 0017363825 scopus 로고
    • Resolution of optical isomers by high-pressure liquid chromatography: The separation of benzo[a]pyrene trans-diol derivatives
    • Yang, S.K., Gelboin, H.V., Weber, J.D., Sankaran, V., Fischer, D. and Engel, J.F. (1977) Resolution of optical isomers by high-pressure liquid chromatography: the separation of benzo[a]pyrene trans-diol derivatives. Anal. Biochem., 78, 520-526.
    • (1977) Anal. Biochem. , vol.78 , pp. 520-526
    • Yang, S.K.1    Gelboin, H.V.2    Weber, J.D.3    Sankaran, V.4    Fischer, D.5    Engel, J.F.6
  • 33
    • 0017654259 scopus 로고
    • Efficient resolution of the dihydrodiol derivatives of benzo[a]pyrene by high-pressure liquid chromatography of the related (-)-dimenthoxyacetates
    • Harvey, R.G. and Cho, H. (1977) Efficient resolution of the dihydrodiol derivatives of benzo[a]pyrene by high-pressure liquid chromatography of the related (-)-dimenthoxyacetates. Anal. Biochem., 80, 540-546.
    • (1977) Anal. Biochem. , vol.80 , pp. 540-546
    • Harvey, R.G.1    Cho, H.2
  • 34
    • 0342423948 scopus 로고
    • Assignment of absolute configuration to metabolically formed trans-dihydrodiols of dibenz[a,h]anthracene by two distinct spectroscopic methods
    • Schollmeier, M., Frank, H., Oesch, F. and Platt, K.L. (1986) Assignment of absolute configuration to metabolically formed trans-dihydrodiols of dibenz[a,h]anthracene by two distinct spectroscopic methods. J. Org. Chem., 51, 5368-5372.
    • (1986) J. Org. Chem. , vol.51 , pp. 5368-5372
    • Schollmeier, M.1    Frank, H.2    Oesch, F.3    Platt, K.L.4
  • 35
    • 8944235458 scopus 로고
    • PhD thesis, University of Mainz, Mainz, Germany
    • Funk, M. (1992) PhD thesis, University of Mainz, Mainz, Germany.
    • (1992)
    • Funk, M.1
  • 36
  • 37
    • 0001610152 scopus 로고
    • Synthesis and assignment of absolute configuration to the trans-3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo[c]phenanthrene
    • Yagi, H., Thakker, D.R., Ittah, M., Croisy-Delcey, M. and Jerina, D.M. (1983) Synthesis and assignment of absolute configuration to the trans-3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo[c]phenanthrene. Tetrahedron Lett., 24, 1349-1352.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1349-1352
    • Yagi, H.1    Thakker, D.R.2    Ittah, M.3    Croisy-Delcey, M.4    Jerina, D.M.5
  • 38
    • 0000294613 scopus 로고
    • An improved synthesis of anti-benzo[c]phenanthrene-3,4-diol 1,2-epoxide via 4-methoxy-benzo[c]-phenanthrene
    • Misra, B. and Amin, S. (1991) An improved synthesis of anti-benzo[c]phenanthrene-3,4-diol 1,2-epoxide via 4-methoxy-benzo[c]-phenanthrene. J. Org. Chem., 55, 4478-4480.
    • (1991) J. Org. Chem. , vol.55 , pp. 4478-4480
    • Misra, B.1    Amin, S.2
  • 39
    • 0000960731 scopus 로고
    • Syntheses of optically active fjord-region 11,12-diol 13,14-epoxides and the K-region 9,10-oxide of the carcinogen benzo[g]chrysene
    • Bushman, D.R., Grossman, S.J., Jerina, D.M. and Lehr, R.E. (1989) Syntheses of optically active fjord-region 11,12-diol 13,14-epoxides and the K-region 9,10-oxide of the carcinogen benzo[g]chrysene. J. Org. Chem., 54, 3533-3544.
    • (1989) J. Org. Chem. , vol.54 , pp. 3533-3544
    • Bushman, D.R.1    Grossman, S.J.2    Jerina, D.M.3    Lehr, R.E.4
  • 40
    • 0020523971 scopus 로고
    • Effects of pH and salt concentration on the hydrolysis of a benzo[a]pyrene 7,8-diol-9,10-epoxide catalyzed by DNA and polyadenylic acid
    • Michaud, D.P., Gupta, S.C., Whalen, D.L., Sayer, J.M. and Jerina, D.M. (1983) Effects of pH and salt concentration on the hydrolysis of a benzo[a]pyrene 7,8-diol-9,10-epoxide catalyzed by DNA and polyadenylic acid. Chem.-Biol. Interactions, 44, 41-52.
    • (1983) Chem.-Biol. Interactions , vol.44 , pp. 41-52
    • Michaud, D.P.1    Gupta, S.C.2    Whalen, D.L.3    Sayer, J.M.4    Jerina, D.M.5
  • 41
    • 0026817379 scopus 로고
    • Heterologous expression of recombinant human glulathione transferase AI-1 from a hepatoma cell line
    • Stenberg, G., Björnestedt, R. and Mannervik, B. (1992) Heterologous expression of recombinant human glulathione transferase AI-1 from a hepatoma cell line. Protein Expression Purificat., 3, 80-84
    • (1992) Protein Expression Purificat. , vol.3 , pp. 80-84
    • Stenberg, G.1    Björnestedt, R.2    Mannervik, B.3
  • 42
    • 0029645124 scopus 로고
    • Structural analysis of human alpha-class glutathione transferase AI-1 in the apo-form and in complexes with ethacrynic acid and its glutathione conjugate
    • Cameron, A.D., Sinning, I., L'Hermite, G., Olin, B., Board, P.G., Mannervik, B. and Jones, T.A. (1995) Structural analysis of human alpha-class glutathione transferase AI-1 in the apo-form and in complexes with ethacrynic acid and its glutathione conjugate. Structure, 3, 717-727
    • (1995) Structure , vol.3 , pp. 717-727
    • Cameron, A.D.1    Sinning, I.2    L'Hermite, G.3    Olin, B.4    Board, P.G.5    Mannervik, B.6    Jones, T.A.7
  • 43
    • 0019741605 scopus 로고
    • Assays for differentiation of glutathione S-transferases
    • Habig, W.H. and Jakoby, W.B. (1981) Assays for differentiation of glutathione S-transferases. Methods Enzymol., 77, 398-405.
    • (1981) Methods Enzymol. , vol.77 , pp. 398-405
    • Habig, W.H.1    Jakoby, W.B.2
  • 44
    • 0024269217 scopus 로고
    • Glutathione transferases-structure and catalytic activity
    • Mannervik, B. and Danielson, U.H. (1988) Glutathione transferases-structure and catalytic activity. CRC Crit. Rev. Biochem., 23, 283-337.
    • (1988) CRC Crit. Rev. Biochem. , vol.23 , pp. 283-337
    • Mannervik, B.1    Danielson, U.H.2
  • 46
    • 0028151320 scopus 로고
    • Contribution of amino acid residue 208 in the hydrophobic binding site Io the catalytic mechanism of human glutathione transferase AI-1
    • Widersten, M., Björnestedt, R. and Mannervik, B (1994) Contribution of amino acid residue 208 in the hydrophobic binding site Io the catalytic mechanism of human glutathione transferase AI-1. Biochemistry, 33, 11717-11723
    • (1994) Biochemistry , vol.33 , pp. 11717-11723
    • Widersten, M.1    Björnestedt, R.2    Mannervik, B.3
  • 47
    • 0028061909 scopus 로고
    • Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene
    • Luch, A., Glatt, H., Platt, K.L., Oesch, F. and Seidel, A. (1994) Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene. Carcinogenesis, 15, 2507-2516.
    • (1994) Carcinogenesis , vol.15 , pp. 2507-2516
    • Luch, A.1    Glatt, H.2    Platt, K.L.3    Oesch, F.4    Seidel, A.5
  • 48
    • 0000784270 scopus 로고
    • Conformational effects in the hydrolysis of benzo-ring diol epoxides that have bay region diol groups
    • Sayer, J.M., Whalen, D.L., Friedman, S.L., Paik, A., Yagi, H., Vyas, K.P. and Jerina, D.M. (1984) Conformational effects in the hydrolysis of benzo-ring diol epoxides that have bay region diol groups. J. Am. Chem. Soc., 106, 226-233.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 226-233
    • Sayer, J.M.1    Whalen, D.L.2    Friedman, S.L.3    Paik, A.4    Yagi, H.5    Vyas, K.P.6    Jerina, D.M.7
  • 49
    • 0023445343 scopus 로고
    • Structure-activity relationships of 4-hydroxyalkenals in the conjugation catalyzed by mammalian glutathione transferases
    • Danielsson, U.H., Esterbauer, H. and Mannervik, B (1987) Structure-activity relationships of 4-hydroxyalkenals in the conjugation catalyzed by mammalian glutathione transferases. Biochem. J., 247, 707-7133
    • (1987) Biochem. J. , vol.247 , pp. 707-7133
    • Danielsson, U.H.1    Esterbauer, H.2    Mannervik, B.3
  • 51
    • 0027209602 scopus 로고
    • Structure determination and refinement of human Alpha class glutalhione transferase AI-1, and a comparison with the Mu and Pi class enzymes
    • Sinning, I. et al. (1993) Structure determination and refinement of human Alpha class glutalhione transferase AI-1, and a comparison with the Mu and Pi class enzymes. J. Mol. Biol., 232, 192-212.
    • (1993) J. Mol. Biol. , vol.232 , pp. 192-212
    • Sinning, I.1
  • 52
    • 0001306237 scopus 로고
    • Human glutathione transferases: Classification, tissue distribution, structure and functional properties
    • Pacifici, G.M. and Fracchia, G.N. (eds). European Commission, Luxembourg, Luxembourg
    • Mannervik, B. and Widersten, M. (1995) Human glutathione transferases: classification, tissue distribution, structure and functional properties. In Pacifici, G.M. and Fracchia, G.N. (eds), Advances in Drug Metabolism in Man. European Commission, Luxembourg, Luxembourg, pp. 408-459.
    • (1995) Advances in Drug Metabolism in Man , pp. 408-459
    • Mannervik, B.1    Widersten, M.2
  • 53
    • 0017752734 scopus 로고
    • Metabolism of benzo[a]pyrene with isolated hepatocytes and the formation and degradation of DNA-binding derivatives
    • Burke, M.D,. Vadi, H., Jernstrom, B. and Orrenius, S. (1977) Metabolism of benzo[a]pyrene with isolated hepatocytes and the formation and degradation of DNA-binding derivatives. J. Biol. Chem., 252, 6424-6431.
    • (1977) J. Biol. Chem. , vol.252 , pp. 6424-6431
    • Burke, M.D.1    Vadi, H.2    Jernstrom, B.3    Orrenius, S.4
  • 54
    • 0019251408 scopus 로고
    • Metabolism of benzo[a]pyrene by isolated hepatocytes and factors affecting covalent binding of benzo[a]pyrene metabolites in hepatocytes and microsomal systems
    • Shen, A.L., Fahl, W.E. and Jefcoate, C.R. (1980) Metabolism of benzo[a]pyrene by isolated hepatocytes and factors affecting covalent binding of benzo[a]pyrene metabolites in hepatocytes and microsomal systems. Arch. Biochem. Biophys., 204, 511-523.
    • (1980) Arch. Biochem. Biophys. , vol.204 , pp. 511-523
    • Shen, A.L.1    Fahl, W.E.2    Jefcoate, C.R.3
  • 55
    • 0020316718 scopus 로고
    • Glutathione conjugation and DNA-binding of (±)-trans-7,8-dihydroxy 7,8 dihydrobenzo[a]pyrene and (±)-7β,8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in isolated rat hepatocytes
    • Jernström, B., Babson, J.R., Moldéus, P., Holmgren, A. and Reed, D.J. (1982) Glutathione conjugation and DNA-binding of (±)-trans-7,8-dihydroxy 7,8 dihydrobenzo[a]pyrene and (±)-7β,8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in isolated rat hepatocytes. Carcinogenesis, 3, 861-866.
    • (1982) Carcinogenesis , vol.3 , pp. 861-866
    • Jernström, B.1    Babson, J.R.2    Moldéus, P.3    Holmgren, A.4    Reed, D.J.5
  • 56
    • 0021170747 scopus 로고
    • Modification of glutathione levels in C3H/10T1/2 cells and its relationship to benzo[a]pyrene anti-7,8-dihydrodiol 9,10-epoxide-induced cytotoxicity
    • Ho, D. and Fahl, W.E. (1984) Modification of glutathione levels in C3H/ 10T1/2 cells and its relationship to benzo[a]pyrene anti-7,8-dihydrodiol 9,10-epoxide-induced cytotoxicity. J. Biol. Chem., 259, 11231-11235.
    • (1984) J. Biol. Chem. , vol.259 , pp. 11231-11235
    • Ho, D.1    Fahl, W.E.2


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