메뉴 건너뛰기




Volumn 25, Issue 3, 2012, Pages 706-712

Conjugation of butadiene diepoxide with glutathione yields DNA adducts in vitro and in vivo

Author keywords

[No Author keywords available]

Indexed keywords

BUTADIENE DIEPOXIDE; DNA; GLUTATHIONE; GLUTATHIONE TRANSFERASE;

EID: 84858686225     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200471x     Document Type: Article
Times cited : (17)

References (49)
  • 1
    • 0025349688 scopus 로고
    • Analysis of low molecular weight hydrocarbons including 1,3-butadiene in engine exhaust gases using an aluminum oxide porous-layer open-tubular fused-silica column
    • Pelz, N., Dempster, N. M., and Shore, P. R. (1990) Analysis of low molecular weight hydrocarbons including 1,3-butadiene in engine exhaust gases using an aluminum oxide porous-layer open-tubular fused-silica column. J. Chromatogr. Sci. 28, 230-235. (Pubitemid 20162599)
    • (1990) Journal of Chromatographic Science , vol.28 , Issue.5 , pp. 230-235
    • Pelz, N.1    Dempster, N.M.2    Shore, P.R.3
  • 2
    • 0025024861 scopus 로고
    • The industrial production and use of 1,3-butadiene
    • Morrow, N. L. (1990) The industrial production and use of 1,3-butadiene. Environ. Health Perspect. 86, 7-8.
    • (1990) Environ. Health Perspect. , vol.86 , pp. 7-8
    • Morrow, N.L.1
  • 4
    • 0027792055 scopus 로고
    • 1,3-Butadiene induces cancer in experimental animals at all concentrations from 6.25 to 8000 parts per million
    • Melnick, R. L., and Huff, J. E. (1993) 1,3-Butadiene induces cancer in experimental animals at all concentrations from 6.25 to 8000 parts per million. IARC Sci. Publ., 309-322.
    • (1993) IARC Sci. Publ. , pp. 309-322
    • Melnick, R.L.1    Huff, J.E.2
  • 5
    • 0030605087 scopus 로고    scopus 로고
    • Metabolism of 1,3-butadiene: Species differences
    • DOI 10.1016/0300-483X(96)03422-1
    • Henderson, R. F., Thornton-Manning, J. R., Bechtold, W. E., and Dahl, A. R. (1996) Metabolism of 1,3-butadiene: species differences. Toxicology 113, 17-22. (Pubitemid 26364069)
    • (1996) Toxicology , vol.113 , Issue.1-3 , pp. 17-22
    • Henderson, R.F.1    Thornton-Manning, J.R.2    Bechtold, W.E.3    Dahl, A.R.4
  • 6
    • 0035366862 scopus 로고    scopus 로고
    • 1,3-Butadiene, isoprene and chloroprene: Reviews by the IARC monographs programme, outstanding issues, and research priorities in epidemiology
    • DOI 10.1016/S0009-2797(01)00175-2, PII S0009279701001752
    • Rice, J. M., and Boffetta, P. (2001) 1,3-Butadiene, isoprene and chloroprene: reviews by the IARC monographs programme, outstanding issues, and research priorities in epidemiology. Chem.-Biol. Interact. 135-136, 11-26. (Pubitemid 32536775)
    • (2001) Chemico-Biological Interactions , vol.135-136 , pp. 11-26
    • Rice, J.M.1    Boffetta, P.2
  • 8
    • 0020078715 scopus 로고
    • Hepatic microsomal metabolism of 1,3-butadiene
    • Malvoisin, E., and Roberfroid, M. (1982) Hepatic microsomal metabolism of 1,3-butadiene. Xenobiotica 12, 137-144. (Pubitemid 12158566)
    • (1982) Xenobiotica , vol.12 , Issue.2 , pp. 137-144
    • Malvoisin, E.1    Roberfroid, M.2
  • 9
    • 0030605125 scopus 로고    scopus 로고
    • Metabolism of 1,3-butadiene: Inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice
    • DOI 10.1016/0300-483X(96)03462-2
    • Himmelstein, M. W., Turner, M. J., Asgharian, B., and Bond, J. A. (1996) Metabolism of 1,3-butadiene: Inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice. Toxicology 113, 306-309. (Pubitemid 26364109)
    • (1996) Toxicology , vol.113 , Issue.1-3 , pp. 306-309
    • Himmelstein, M.W.1    Turner, M.J.2    Asgharian, B.3    Bond, J.A.4
  • 10
    • 33646090404 scopus 로고    scopus 로고
    • Characterization of 1,2,3,4-diepoxybutane-2′-deoxyguanosine cross-linking products formed at physiological and nonphysiological conditions
    • Zhang, X. Y., and Elfarra, A. A. (2006) Characterization of 1,2,3,4-diepoxybutane-2′-deoxyguanosine cross-linking products formed at physiological and nonphysiological conditions. Chem. Res. Toxicol. 19, 547-555.
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 547-555
    • Zhang, X.Y.1    Elfarra, A.A.2
  • 11
    • 0030802222 scopus 로고    scopus 로고
    • Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane
    • DOI 10.1021/tx970004q
    • Tretyakova, N., Sangaiah, R., Yen, T. Y., and Swenberg, J. A. (1997) Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane. Chem. Res. Toxicol. 10, 779-785. (Pubitemid 27315111)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.7 , pp. 779-785
    • Tretyakova, N.Yu.1    Sangaiah, R.2    Yen, T.-Y.3    Swenberg, J.A.4
  • 12
    • 0030754684 scopus 로고    scopus 로고
    • Adenine adducts with diepoxybutane: Isolation and analysis in exposed calf thymus DNA
    • DOI 10.1021/tx9700681
    • Tretyakova, N., Sangaiah, R., Yen, T. Y., Gold, A., and Swenberg, J. A. (1997) Adenine adducts with diepoxybutane: Isolation and analysis in exposed calf thymus DNA. Chem. Res. Toxicol. 10, 1171-1179. (Pubitemid 27449521)
    • (1997) Chemical Research in Toxicology , vol.10 , Issue.10 , pp. 1171-1179
    • Tretyakova, N.1    Sangaiah, R.2    Yen, T.-Y.3    Gold, A.4    Swenberg, J.A.5
  • 14
    • 0031408197 scopus 로고    scopus 로고
    • Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide
    • DOI 10.1093/carcin/18.10.1993
    • Selzer, R. R., and Elfarra, A. A. (1997) Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide. Carcinogenesis 18, 1993-1998. (Pubitemid 28132386)
    • (1997) Carcinogenesis , vol.18 , Issue.10 , pp. 1993-1998
    • Selzer, R.R.1    Elfarra, A.A.2
  • 15
    • 0029662162 scopus 로고    scopus 로고
    • Characterization of N1- And N6-adenosine adducts and N1-inosine adducts formed by the reaction of butadiene monoxide with adenosine: Evidence for the N1-adenosine adducts as major initial products
    • Selzer, R. R., and Elfarra, A. A. (1996) Characterization of N1- and N6-adenosine adducts and N1-inosine adducts formed by the reaction of butadiene monoxide with adenosine: evidence for the N1-adenosine adducts as major initial products. Chem. Res. Toxicol. 9, 875-881.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 875-881
    • Selzer, R.R.1    Elfarra, A.A.2
  • 16
    • 33746255333 scopus 로고    scopus 로고
    • Synthesis and mutagenesis of the butadiene-derived N3 2′-deoxyuridine adducts
    • DOI 10.1021/tx060016o
    • Fernandes, P. H., Hackfeld, L. C., Kozekov, I. D., Hodge, R. P., and Lloyd, R. S. (2006) Synthesis and mutagenesis of the butadiene-derived N3 2′-deoxyuridine adducts. Chem. Res. Toxicol. 19, 968-976. (Pubitemid 44092363)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.7 , pp. 968-976
    • Fernandes, P.H.1    Hackfeld, L.C.2    Kozekov, I.D.3    Hodge, R.P.4    Lloyd, R.S.5
  • 17
    • 0021338990 scopus 로고
    • The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: Synthesis and characterization of the main adducts
    • Citti, L., Gervasi, P. G., Turchi, G., Bellucci, G., and Bianchini, R. (1984) The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: Synthesis and characterization of the main adducts. Carcinogenesis 5, 47-52. (Pubitemid 14197925)
    • (1984) Carcinogenesis , vol.5 , Issue.1 , pp. 47-52
    • Citti, L.1    Gervasi, P.G.2    Turchi, G.3
  • 18
    • 0023183193 scopus 로고
    • Comparative cytogenetic analysis of bone marrow damage induced in male B6C3F1 mice by multiple exposures to gaseous 1,3-butadiene
    • Tice, R. R., Boucher, R., Luke, C. A., and Shelby, M. D. (1987) Comparative cytogenetic analysis of bone marrow damage induced in male B6C3F1 mice by multiple exposures to gaseous 1,3-butadiene. Environ. Mutagen. 9, 235-250. (Pubitemid 17114576)
    • (1987) Environmental Mutagenesis , vol.9 , Issue.3 , pp. 235-250
    • Tice, R.R.1    Boucher, R.2    Luke, C.A.3    Shelby, M.D.4
  • 19
    • 0028026138 scopus 로고
    • Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in splenic T cells from exposed B6C3F1 mice
    • Cochrane, J. E., and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in splenic T cells from exposed B6C3F1 mice. Carcinogenesis 15, 719-723.
    • (1994) Carcinogenesis , vol.15 , pp. 719-723
    • Cochrane, J.E.1    Skopek, T.R.2
  • 20
    • 0027951237 scopus 로고
    • Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts
    • Cochrane, J. E., and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts. Carcinogenesis 15, 713-717. (Pubitemid 24124417)
    • (1994) Carcinogenesis , vol.15 , Issue.4 , pp. 713-717
    • Cochrane, J.E.1    Skopek, T.R.2
  • 22
    • 65549093299 scopus 로고    scopus 로고
    • Molecular dosimetry of 1,2,3,4-diepoxybutane-induced DNA-DNA cross-links in B6C3F1 mice and F344 rats exposed to 1,3-butadiene by inhalation
    • Goggin, M., Swenberg, J. A., Walker, V. E., and Tretyakova, N. (2009) Molecular dosimetry of 1,2,3,4-diepoxybutane-induced DNA-DNA cross-links in B6C3F1 mice and F344 rats exposed to 1,3-butadiene by inhalation. Cancer Res. 69, 2479-2486.
    • (2009) Cancer Res. , vol.69 , pp. 2479-2486
    • Goggin, M.1    Swenberg, J.A.2    Walker, V.E.3    Tretyakova, N.4
  • 23
    • 26644437215 scopus 로고    scopus 로고
    • Identification of mammalian proteins cross-linked to DNA by ionizing radiation
    • DOI 10.1074/jbc.M502477200
    • Barker, S., Weinfeld, M., Zheng, J., Li, L., and Murray, D. (2005) Identification of mammalian proteins cross-linked to DNA by ionizing radiation. J. Biol. Chem. 280, 33826-33838. (Pubitemid 41443102)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.40 , pp. 33826-33838
    • Barker, S.1    Weinfeld, M.2    Zheng, J.3    Li, L.4    Murray, D.5
  • 24
    • 15944429355 scopus 로고    scopus 로고
    • DNA-protein crosslinks: Their induction, repair, and biological consequences
    • DOI 10.1016/j.mrrev.2004.11.003
    • Barker, S., Weinfeld, M., and Murray, D. (2005) DNA-protein crosslinks: Their induction, repair, and biological consequences. Mutat. Res. 589, 111-135. (Pubitemid 40431691)
    • (2005) Mutation Research - Reviews in Mutation Research , vol.589 , Issue.2 , pp. 111-135
    • Barker, S.1    Weinfeld, M.2    Murray, D.3
  • 25
    • 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
    • DOI 10.1006/abbi.1996.9781
    • 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. (Pubitemid 27198180)
    • (1997) Archives of Biochemistry and Biophysics , vol.337 , Issue.2 , pp. 176-184
    • Krause, R.J.1    Elfarra, A.A.2
  • 26
    • 0031879942 scopus 로고    scopus 로고
    • Stereochemical aspects of the conjugation of epoxide metabolites of butadiene with glutathione in rat liver cytosol and freshly isolated rat hepatocytes
    • DOI 10.1006/toxs.1998.2461
    • Nieusma, J. L., Claffey, D. J., Ruth, J. A., and Ross, D. (1998) Stereochemical aspects of the conjugation of epoxide metabolites of butadiene with glutathione in rat liver cytosol and freshly isolated rat hepatocytes. Toxicol. Sci. 43, 102-109. (Pubitemid 28363383)
    • (1998) Toxicological Sciences , vol.43 , Issue.2 , pp. 102-109
    • Nieusma, J.L.1    Claffey, D.J.2    Ruth, J.A.3    Ross, D.4
  • 27
    • 34250789211 scopus 로고    scopus 로고
    • Mutagenesis of the supF gene by stereoisomers of 1,2,3,4-diepoxybutane
    • DOI 10.1021/tx700003b
    • Kim, M. Y., Tretyakova, N., and Wogan, G. N. (2007) Mutagenesis of the supF gene by stereoisomers of 1,2,3,4-diepoxybutane. Chem. Res. Toxicol. 20, 790-797. (Pubitemid 46953686)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.5 , pp. 790-797
    • Min, Y.K.1    Tretyakova, N.2    Wogan, G.N.3
  • 28
    • 26844435658 scopus 로고
    • Mutagenic activity of isomeric forms of diepoxybutane in maize
    • Bianchi, A., and Contin, M. (1962) Mutagenic activity of isomeric forms of diepoxybutane in maize. J. Hered. 53, 277-281.
    • (1962) J. Hered. , vol.53 , pp. 277-281
    • Bianchi, A.1    Contin, M.2
  • 30
    • 0028930987 scopus 로고
    • Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase
    • Thier, R., Muller, M., Taylor, J. B., Pemble, S. E., Ketterer, B., and Guengerich, F. P. (1995) Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione S-transferase. Chem. Res. Toxicol. 8, 465-472.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 465-472
    • Thier, R.1    Muller, M.2    Taylor, J.B.3    Pemble, S.E.4    Ketterer, B.5    Guengerich, F.P.6
  • 31
    • 0029947171 scopus 로고    scopus 로고
    • Human glutathione S-transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane and 1,2,3,4-diepoxybutane in Salmonella typhimurium
    • DOI 10.1093/carcin/17.1.163
    • Thier, R., Pemble, S. E., Kramer, H., Taylor, J. B., Guengerich, F. P., and Ketterer, B. (1996) Human glutathione S-transferase T1-1 enhances mutagenicity of 1,2-dibromoethane, dibromomethane and 1,2,3,4-diepoxybutane in Salmonella typhimurium. Carcinogenesis 17, 163-166. (Pubitemid 26091288)
    • (1996) Carcinogenesis , vol.17 , Issue.1 , pp. 163-166
    • Thier, R.1    Pemble, S.E.2    Kramer, H.3    Taylor, J.B.4    Guengerich, F.P.5    Ketterer, B.6
  • 32
    • 77958088974 scopus 로고    scopus 로고
    • Mutagenicity of a glutathione conjugate of butadiene diepoxide
    • Cho, S. H., Loecken, E. M., and Guengerich, F. P. (2010) Mutagenicity of a glutathione conjugate of butadiene diepoxide. Chem. Res. Toxicol. 23, 1544-1546.
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 1544-1546
    • Cho, S.H.1    Loecken, E.M.2    Guengerich, F.P.3
  • 33
    • 85027732552 scopus 로고    scopus 로고
    • Synthesis of chiral non-racemic diols from (S,S)-1,2,3,4-diepoxybutane: (2S,3S)-dihydroxy-1,4-diphenylbutane (2,2′-bioxirane, [S-(R,R)]- And 2,3-butanediol, 1,4-diphenyl-, [S-(R,R)]-)
    • Robbins, M. A., Devine, P. N., and Oh, T. (1999) Synthesis of chiral non-racemic diols from (S,S)-1,2,3,4-diepoxybutane: (2S,3S)-dihydroxy-1,4- diphenylbutane (2,2′-bioxirane, [S-(R,R)]- and 2,3-butanediol, 1,4-diphenyl-, [S-(R,R)]-). Org. Synth. 76, 101-109.
    • (1999) Org. Synth. , vol.76 , pp. 101-109
    • Robbins, M.A.1    Devine, P.N.2    Oh, T.3
  • 34
    • 0002818786 scopus 로고
    • 1,4-Di-O-alkyl threitols from tartaric acid: 1,4-Di-O-benzyl-L-threitol
    • Mash, E. A., Nelson, K. A., Van Deusen, S., and Hemperly, S. B. (1990) 1,4-Di-O-alkyl threitols from tartaric acid: 1,4-Di-O-benzyl-L-threitol. Org. Synth. 68, 92-103.
    • (1990) Org. Synth. , vol.68 , pp. 92-103
    • Mash, E.A.1    Nelson, K.A.2    Van Deusen, S.3    Hemperly, S.B.4
  • 35
    • 0036383950 scopus 로고    scopus 로고
    • Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide
    • Claffey, D. J. (2002) Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide. Synth. Commun. 32, 3041-3045.
    • (2002) Synth. Commun. , vol.32 , pp. 3041-3045
    • Claffey, D.J.1
  • 36
    • 0020533372 scopus 로고
    • Revised methods for the Salmonella mutagenicity test
    • Maron, D. M., and Ames, B. N. (1983) Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113, 173-215. (Pubitemid 13120319)
    • (1983) Mutation Research , vol.113 , Issue.3-4 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 37
    • 0014984181 scopus 로고
    • Chemical modifications of transfer RNA species. Desulfurization with Raney nickel
    • Hecht, S. M., Kirkegaard, L. H., and Bock, R. M. (1971) Chemical modifications of transfer RNA species. Desulfurization with Raney nickel. Proc. Natl. Acad. Sci. U.S.A. 68, 48-51.
    • (1971) Proc. Natl. Acad. Sci. U.S.A. , vol.68 , pp. 48-51
    • Hecht, S.M.1    Kirkegaard, L.H.2    Bock, R.M.3
  • 38
    • 0025190253 scopus 로고
    • Formation of the DNA adduct S-[2-(N7-guanyl)ethyl]glutathione from ethylene dibromide: Effects of modulation of glutathione and glutathione S-transferase levels and lack of a role for sulfation
    • Kim, D. H., and Guengerich, F. P. (1990) Formation of the DNA adduct S-[2-(N7-guanyl)ethyl]glutathione from ethylene dibromide: Effects of modulation of glutathione and glutathione S-transferase levels and lack of a role for sulfation. Carcinogenesis 11, 419-424.
    • (1990) Carcinogenesis , vol.11 , pp. 419-424
    • Kim, D.H.1    Guengerich, F.P.2
  • 41
    • 0024306062 scopus 로고
    • Species differences in DNA damage by butadiene: Role of diepoxybutane
    • Jelitto, B., Vangala, R. R., and Laib, R. J. (1989) Species differences in DNA damage by butadiene: Role of diepoxybutane. Arch. Toxicol. Suppl. 13, 246-249. (Pubitemid 19207663)
    • (1989) Archives of Toxicology , vol.63 , Issue.SUPPL. 13 , pp. 246-249
    • Jelitto, B.1    Vangala, R.R.2    Laib, R.J.3
  • 42
    • 33744501244 scopus 로고    scopus 로고
    • 6-alkylguanine DNA alkyltransferase to DNA in the presence of 1,2,3,4-diepoxybutane
    • DOI 10.1021/tx0600088
    • Loeber, R., Rajesh, M., Fang, Q., Pegg, A. E., and Tretyakova, N. (2006) Cross-linking of the human DNA repair protein O6-alkylguanine DNA alkyltransferase to DNA in the presence of 1,2,3,4-diepoxybutane. Chem. Res. Toxicol. 19, 645-654. (Pubitemid 43800980)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.5 , pp. 645-654
    • Loeber, R.1    Rajesh, M.2    Fang, Q.3    Pegg, A.E.4    Tretyakova, N.5
  • 43
    • 41649093578 scopus 로고    scopus 로고
    • Reactions of glyceraldehyde 3-phosphate dehydrogenase sulfhydryl groups with bis-electrophiles produce DNA-protein cross-links but not mutations
    • Loecken, E. M., and Guengerich, F. P. (2008) Reactions of glyceraldehyde 3-phosphate dehydrogenase sulfhydryl groups with bis-electrophiles produce DNA-protein cross-links but not mutations. Chem. Res. Toxicol. 21, 453-458.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 453-458
    • Loecken, E.M.1    Guengerich, F.P.2
  • 44
    • 67449113183 scopus 로고    scopus 로고
    • The bis-electrophile diepoxybutane cross-links DNA to human histones but does not result in enhanced mutagenesis in recombinant systems
    • Loecken, E. M., Dasari, S., Hill, S., Tabb, D. L., and Guengerich, F. P. (2009) The bis-electrophile diepoxybutane cross-links DNA to human histones but does not result in enhanced mutagenesis in recombinant systems. Chem. Res. Toxicol. 22, 1069-1076.
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 1069-1076
    • Loecken, E.M.1    Dasari, S.2    Hill, S.3    Tabb, D.L.4    Guengerich, F.P.5
  • 45
    • 26844432462 scopus 로고    scopus 로고
    • Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4- diepoxybutane: Role of stereochemistry
    • DOI 10.1021/ja051979x
    • Park, S., Anderson, C., Loeber, R., Seetharaman, M., Jones, R., and Tretyakova, N. (2005) Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: Role of stereochemistry. J. Am. Chem. Soc. 127, 14355-14365. (Pubitemid 41457596)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.41 , pp. 14355-14365
    • Park, S.1    Anderson, C.2    Loeber, R.3    Seetharaman, M.4    Jones, R.5    Tretyakova, N.6
  • 46
    • 10844236473 scopus 로고    scopus 로고
    • Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: Potential basis for biological activity
    • DOI 10.1021/tx0498206
    • Park, S., Hodge, J., Anderson, C., and Tretyakova, N. (2004) Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: Potential basis for biological activity. Chem. Res. Toxicol. 17, 1638-1651. (Pubitemid 39665556)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.12 , pp. 1638-1651
    • Park, S.1    Hodge, J.2    Anderson, C.3    Tretyakova, N.4
  • 47
    • 77951246489 scopus 로고    scopus 로고
    • Column switching HPLC-ESI(+)-MS/MS methods for quantitative analysis of exocyclic dA adducts in the DNA of laboratory animals exposed to 1,3-butadiene
    • Goggin, M., Seneviratne, U., Swenberg, J. A., Walker, V. E., and Tretyakova, N. (2010) Column switching HPLC-ESI(+)-MS/MS methods for quantitative analysis of exocyclic dA adducts in the DNA of laboratory animals exposed to 1,3-butadiene. Chem. Res. Toxicol. 23, 808-812.
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 808-812
    • Goggin, M.1    Seneviratne, U.2    Swenberg, J.A.3    Walker, V.E.4    Tretyakova, N.5
  • 48
    • 79959436462 scopus 로고    scopus 로고
    • Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation
    • Goggin, M., Sangaraju, D., Walker, V. E., Wickliffe, J., Swenberg, J. A., and Tretyakova, N. (2011) Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation. Chem. Res. Toxicol. 24, 809-817.
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 809-817
    • Goggin, M.1    Sangaraju, D.2    Walker, V.E.3    Wickliffe, J.4    Swenberg, J.A.5    Tretyakova, N.6
  • 49
    • 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
    • DOI 10.1006/taap.1996.0037
    • 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. (Pubitemid 26070895)
    • (1996) Toxicology and Applied Pharmacology , vol.136 , Issue.2 , pp. 307-316
    • Boogaard, P.J.1    Sumner, S.C.-J.2    Bond, J.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.