메뉴 건너뛰기




Volumn 43, Issue 2, 1998, Pages 102-109

Stereochemical aspects of the conjugation of epoxide metabolites of butadiene with glutathione in rat liver cytosol and freshly isolated rat hepatocytes

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; EPOXIDE; GLUTATHIONE;

EID: 0031879942     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1006/toxs.1998.2461     Document Type: Article
Times cited : (32)

References (39)
  • 1
    • 0024803461 scopus 로고
    • The paradox of butadiene epidemiology
    • Aquavella, J. F. (1989). The paradox of butadiene epidemiology. Exp. Pathol. 37, 114-118.
    • (1989) Exp. Pathol. , vol.37 , pp. 114-118
    • Aquavella, J.F.1
  • 2
    • 0030476283 scopus 로고    scopus 로고
    • The role of hydrolysis in the detoxification of 1,2,3,4-diepoxybutane by human, rat, and mouse liver and lung in vitro
    • Boogaard, P. J., and Bond, J. A. (1996). The role of hydrolysis in the detoxification of 1,2,3,4-diepoxybutane by human, rat, and mouse liver and lung in vitro. Toxicol. Appl. Pharmacol. 141, 617-627.
    • (1996) Toxicol. Appl. Pharmacol. , vol.141 , pp. 617-627
    • Boogaard, P.J.1    Bond, J.A.2
  • 3
    • 0030039686 scopus 로고    scopus 로고
    • Glutathione conjugation of 1,2,3,4-diepoxybutane in human liver and rat and mouse liver and lung in vitro
    • Boogaard, P. J., Sumner, S. C., and Bond, J. A. (1996). Glutathione conjugation of 1,2,3,4-diepoxybutane in human liver and rat and mouse liver and lung in vitro. Toxicol. Appl. Pharmacol. 136, 307-316.
    • (1996) Toxicol. Appl. Pharmacol. , vol.136 , pp. 307-316
    • Boogaard, P.J.1    Sumner, S.C.2    Bond, J.A.3
  • 4
    • 0030995364 scopus 로고    scopus 로고
    • Comparison of mouse strains for susceptibility to styrene-induced hepatotoxicity and pneumotoxicity
    • Carlson, G. P. (1997). Comparison of mouse strains for susceptibility to styrene-induced hepatotoxicity and pneumotoxicity. J. Toxicol. Environ Health 51, 177-187.
    • (1997) J. Toxicol. Environ Health , vol.51 , pp. 177-187
    • Carlson, G.P.1
  • 5
    • 0023479266 scopus 로고
    • Role of diaxial versus diequatorial hydroxyl groups in the tumorigenic activity of a benzo[a]pyrene bay-region diol epoxide
    • Chang, R. L., Wood, W. W., Conney, A. H., Yagi, H., Sayer, J. M., Thakker, D. R., Jerina, D. M., and Levin, W. (1987). Role of diaxial versus diequatorial hydroxyl groups in the tumorigenic activity of a benzo[a]pyrene bay-region diol epoxide. Proc. Natl. Acad. Sci. USA 84, 8633-8636.
    • (1987) Proc. Natl. Acad. Sci. USA , vol.84 , pp. 8633-8636
    • Chang, R.L.1    Wood, W.W.2    Conney, A.H.3    Yagi, H.4    Sayer, J.M.5    Thakker, D.R.6    Jerina, D.M.7    Levin, W.8
  • 6
    • 0030605057 scopus 로고    scopus 로고
    • Synthetic route to optically-pure metabolites of butadiene, and their chiral GC separation
    • Claffey, D. J., and Ruth, J. A. (1996). Synthetic route to optically-pure metabolites of butadiene, and their chiral GC separation. Tetrahedron Lett. 37, 7929-7932.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7929-7932
    • Claffey, D.J.1    Ruth, J.A.2
  • 7
    • 0027470084 scopus 로고
    • Exposure to butadiene and lymphatic and hematopoietic cancer
    • Cole, P., Delzell, E., and Acquavella, J. F. (1993). Exposure to butadiene and lymphatic and hematopoietic cancer. Epidemiology 4, 96-103.
    • (1993) Epidemiology , vol.4 , pp. 96-103
    • Cole, P.1    Delzell, E.2    Acquavella, J.F.3
  • 8
    • 0026741034 scopus 로고
    • Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice
    • Csánady, G. A., Guengerich, F. P., and Bond, J. A. (1992). Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice Carcinogenesis 13, 1143-1153.
    • (1992) Carcinogenesis , vol.13 , pp. 1143-1153
    • Csánady, G.A.1    Guengerich, F.P.2    Bond, J.A.3
  • 11
    • 0021671419 scopus 로고
    • Alterations in intracellular thiol homeostasis during the metabolism of menadione by isolated rat hepatocytes
    • Di Monte, D., Ross, D., Bellomo, G., Eklow, L., and Orrenius, S. (1984). Alterations in intracellular thiol homeostasis during the metabolism of menadione by isolated rat hepatocytes. Arch. Biochem. Biophys. 235, 334 -342.
    • (1984) Arch. Biochem. Biophys. , vol.235 , pp. 334-342
    • Di Monte, D.1    Ross, D.2    Bellomo, G.3    Eklow, L.4    Orrenius, S.5
  • 12
    • 0001016239 scopus 로고
    • Preliminary draft list of categories and subcategories under section 112 of the Clean Air Act
    • Environmental Protection Agency (1991). Preliminary draft list of categories and subcategories under section 112 of the Clean Air Act. Fed. Reg. 56, 28548-28557.
    • (1991) Fed. Reg. , vol.56 , pp. 28548-28557
  • 13
  • 14
    • 0021999773 scopus 로고
    • Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds
    • Gervasi, P. G., Citti, L., DelMonte, M., Longo, V., and Benetti, D. (1985) Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds. Mutat. Res. 156, 77-82.
    • (1985) Mutat. Res. , vol.156 , pp. 77-82
    • Gervasi, P.G.1    Citti, L.2    DelMonte, M.3    Longo, V.4    Benetti, D.5
  • 15
    • 0021916824 scopus 로고
    • Multiple organ carcinogenicity of 1,3-butadiene in B6C3F1 mice after 60 weeks of inhalation exposure
    • Huff, J. E., Melnick, R. L., Solleveld, H. A., Haseman, J. K., Powers, M., and Miller, R. A. (1985). Multiple organ carcinogenicity of 1,3-butadiene in B6C3F1 mice after 60 weeks of inhalation exposure. Science 227, 548-549.
    • (1985) Science , vol.227 , pp. 548-549
    • Huff, J.E.1    Melnick, R.L.2    Solleveld, H.A.3    Haseman, J.K.4    Powers, M.5    Miller, R.A.6
  • 17
    • 0027028530 scopus 로고
    • Occupational exposures to mists and vapors from strong inorganic acids and other industrial chemicals, 1,3-butadiene
    • IARC (1992). Occupational exposures to mists and vapors from strong inorganic acids and other industrial chemicals, 1,3-butadiene. IARC Monogr. Eval. Carcinog. Risks Hum. 54, 237-285.
    • (1992) IARC Monogr. Eval. Carcinog. Risks Hum. , vol.54 , pp. 237-285
  • 18
    • 0028785664 scopus 로고
    • Sister chromatid exchanges, glutathione S-transferase theta deletion and cytogenetic sensitivity to diepoxybutane in lymphocytes from butadiene monomer production workers
    • Kelsey, K., Wiencke, J., Ward, J., Bechtold, B., and Fajen, J. (1995). Sister chromatid exchanges, glutathione S-transferase theta deletion and cytogenetic sensitivity to diepoxybutane in lymphocytes from butadiene monomer production workers. Mutat. Res. 335, 267-273.
    • (1995) Mutat. Res. , vol.335 , pp. 267-273
    • Kelsey, K.1    Wiencke, J.2    Ward, J.3    Bechtold, B.4    Fajen, J.5
  • 19
    • 0031568224 scopus 로고    scopus 로고
    • Oxidation of butadiene monoxide to meso- And (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat and human liver microsomes: Evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes
    • Krause, R. J., and Elfarra, A. A. (1997). Oxidation of butadiene monoxide to meso-and (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat and human liver microsomes: Evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes. Arch. Biochem. Biophys. 337, 176-184.
    • (1997) Arch. Biochem. Biophys. , vol.337 , pp. 176-184
    • Krause, R.J.1    Elfarra, A.A.2
  • 20
    • 0030745891 scopus 로고    scopus 로고
    • Epoxide hydrolase-dependent metabolism of butadiene monoxide to 3-butene-1,2-diol in mouse, rat, and human liver
    • Krause, R. J., Sharer, J. E., and Elfarra, A. A. (1997). Epoxide hydrolase-dependent metabolism of butadiene monoxide to 3-butene-1,2-diol in mouse, rat, and human liver. Drug Metab. Dispos. 25, 1013-1015.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 1013-1015
    • Krause, R.J.1    Sharer, J.E.2    Elfarra, A.A.3
  • 21
    • 0342472803 scopus 로고    scopus 로고
    • Flow cytometric analysis of micronucleus induction in rat bone marrow polychromatic erythrocytes by 1,2,3,4-diepoxybutane, 3,4-epoxy-1-butene, and 1,2-epoxybutane-3,4-diol
    • Lähdetie, J., and Grawé. J. (1997). Flow cytometric analysis of micronucleus induction in rat bone marrow polychromatic erythrocytes by 1,2,3,4-diepoxybutane, 3,4-epoxy-1-butene, and 1,2-epoxybutane-3,4-diol. Cytometry 28, 228-235.
    • (1997) Cytometry , vol.28 , pp. 228-235
    • Lähdetie, J.1    Grawé, J.2
  • 22
    • 0020599372 scopus 로고
    • Subcellular distribution and kinetic parameters of HS liver aldehyde dehydrogenase
    • Little, R. G., and Petersen, D. R. (1983). Subcellular distribution and kinetic parameters of HS liver aldehyde dehydrogenase. Comp. Biochem. Physiol. C 74, 271-279.
    • (1983) Comp. Biochem. Physiol. C , vol.74 , pp. 271-279
    • Little, R.G.1    Petersen, D.R.2
  • 24
    • 0028979714 scopus 로고
    • Metabolism of 1,3-butadiene to butadiene monoxide in mouse and human bone marrow cells
    • Maniglier-Poulet, C., Cheng, X., Ruth, J. A., and Ross, D. (1995). Metabolism of 1,3-butadiene to butadiene monoxide in mouse and human bone marrow cells. Chem.-Biol. Interact. 97, 119-129.
    • (1995) Chem.-Biol. Interact. , vol.97 , pp. 119-129
    • Maniglier-Poulet, C.1    Cheng, X.2    Ruth, J.A.3    Ross, D.4
  • 25
    • 0025048644 scopus 로고
    • Carcinogenicity of 1,3-butadiene in C57BL/6 X C3H F1 mice at low concentrations
    • Melnick, R. L., Huff, J. E., Chou, B., and Miller, R. A. (1990). Carcinogenicity of 1,3-butadiene in C57BL/6 X C3H F1 mice at low concentrations. Cancer Res. 50, 659-6599.
    • (1990) Cancer Res. , vol.50 , pp. 659-6599
    • Melnick, R.L.1    Huff, J.E.2    Chou, B.3    Miller, R.A.4
  • 29
    • 0030992927 scopus 로고    scopus 로고
    • Stereochemical aspects of 1,3-butadiene metabolism and toxicity in rat and mouse liver microsomes and freshly isolated rat hepatocytes
    • Nieusma, J. L., Claffey, D. J., Maniglier-Poulet, C., Imiolczyk, T., Ross, D., and Ruth, J. A. (1997). Stereochemical aspects of 1,3-butadiene metabolism and toxicity in rat and mouse liver microsomes and freshly isolated rat hepatocytes. Chem. Res. Toxicol. 10, 450-456.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 450-456
    • Nieusma, J.L.1    Claffey, D.J.2    Maniglier-Poulet, C.3    Imiolczyk, T.4    Ross, D.5    Ruth, J.A.6
  • 30
    • 3543044263 scopus 로고    scopus 로고
    • Oxidation of 1,3-butadiene to (R)- And (S)-butadiene monoxide by purified cytochrome P4502E1 from rabbit, rat and human
    • in press
    • Nieusma, J. L., Claffey, D. J., Ruth, J. A., and Ross, D. (1997). Oxidation of 1,3-butadiene to (R)-and (S)-butadiene monoxide by purified cytochrome P4502E1 from rabbit, rat and human. Toxicol. Lett., in press.
    • (1997) Toxicol. Lett.
    • Nieusma, J.L.1    Claffey, D.J.2    Ruth, J.A.3    Ross, D.4
  • 31
    • 0028990060 scopus 로고
    • Role of GSTT1 and GSTM1 genotypes in determining individual sensitivity to sister chromatid exchange induction by diepoxybutane in cultured human lymphocytes
    • Norppa, H., Hirvonen, A., Jarventaus, H., Uuskula, M., Tasa, G., Ojajarvi, A., and Sorsa, M. (1995). Role of GSTT1 and GSTM1 genotypes in determining individual sensitivity to sister chromatid exchange induction by diepoxybutane in cultured human lymphocytes. Carcinogenesis 16, 1261-1264.
    • (1995) Carcinogenesis , vol.16 , pp. 1261-1264
    • Norppa, H.1    Hirvonen, A.2    Jarventaus, H.3    Uuskula, M.4    Tasa, G.5    Ojajarvi, A.6    Sorsa, M.7
  • 32
    • 0025126208 scopus 로고
    • Inhalation toxicity and carcinogenicity of 1,3-butadiene in Sprague-Dawley rats
    • Owen, P. E., and Glaister, J. R. (1990). Inhalation toxicity and carcinogenicity of 1,3-butadiene in Sprague-Dawley rats. Environ. Health Perspect. 86, 19-25.
    • (1990) Environ. Health Perspect. , vol.86 , pp. 19-25
    • Owen, P.E.1    Glaister, J.R.2
  • 33
    • 0029928663 scopus 로고    scopus 로고
    • Influence of erythrocyte glutathione S-transferase T1 on sister chromatid exchanges induced by diepoxybutane in cultured human lymphocytes
    • Pelin, K., Hirvonen, A., and Norppa, H. (1996). Influence of erythrocyte glutathione S-transferase T1 on sister chromatid exchanges induced by diepoxybutane in cultured human lymphocytes. Mutagenesis 11, 213-215.
    • (1996) Mutagenesis , vol.11 , pp. 213-215
    • Pelin, K.1    Hirvonen, A.2    Norppa, H.3
  • 35
    • 0019131878 scopus 로고
    • High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide and related thiols and disulfides
    • Reed, D. J., Babson, J. R., Beatty, P. W., Brodie, A. E., Ellis, W. W., and Potter, D. W. (1980). High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide and related thiols and disulfides. Anal. Biochem. 106, 55-62.
    • (1980) Anal. Biochem. , vol.106 , pp. 55-62
    • Reed, D.J.1    Babson, J.R.2    Beatty, P.W.3    Brodie, A.E.4    Ellis, W.W.5    Potter, D.W.6
  • 36
    • 0028926133 scopus 로고
    • Influence of GSTM1 genotype on sister chromatid exchange induction by styrene-7,8-oxide and 1,2-epoxy-3-butene in cultured human lymphocytes
    • Uuskula, M., Jarventaus, H., Hirvonen, A., Sorsa, M., and Norppa, H. (1995). Influence of GSTM1 genotype on sister chromatid exchange induction by styrene-7,8-oxide and 1,2-epoxy-3-butene in cultured human lymphocytes. Carcinogenesis 16, 947-950.
    • (1995) Carcinogenesis , vol.16 , pp. 947-950
    • Uuskula, M.1    Jarventaus, H.2    Hirvonen, A.3    Sorsa, M.4    Norppa, H.5
  • 37
    • 0018411986 scopus 로고
    • Mutagenic action in a series of epoxides
    • Wade, M. J., Moyer, J. W., and Hine, C. H. (1979). Mutagenic action in a series of epoxides. Mutat. Res. 66, 367-371.
    • (1979) Mutat. Res. , vol.66 , pp. 367-371
    • Wade, M.J.1    Moyer, J.W.2    Hine, C.H.3
  • 38
    • 0028918081 scopus 로고
    • Gene deletion of glutathione S-transferase theta: Correlation with induced genetic damage and potential role in endogenous mutagenesis
    • Wiencke, J., Pemble, S., Ketterer, B., and Kelsey, K. (1995). Gene deletion of glutathione S-transferase theta: Correlation with induced genetic damage and potential role in endogenous mutagenesis. Cancer Epidemiol. Biomark. Prevent. 4, 253-259.
    • (1995) Cancer Epidemiol. Biomark. Prevent. , vol.4 , pp. 253-259
    • Wiencke, J.1    Pemble, S.2    Ketterer, B.3    Kelsey, K.4
  • 39
    • 0027411281 scopus 로고
    • Mutagenicity of the human carcinogen Treosulphan and its hydrolysis product, dl-1,2,3,4-diepoxybutane in mammalian cells
    • Zhu, S., and Zeiger, E. (1993). Mutagenicity of the human carcinogen Treosulphan and its hydrolysis product, dl-1,2,3,4-diepoxybutane in mammalian cells. Environ. Mol. Mutagen. 21, 95-99.
    • (1993) Environ. Mol. Mutagen. , vol.21 , pp. 95-99
    • Zhu, S.1    Zeiger, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.