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Volumn 20, Issue 5, 2007, Pages 839-847

HPLC-ESI+ -MS/MS analysis of N7-guanine-N7-guanine DNA cross-links in tissues of mice exposed to 1,3-butadiene

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; DNA; GUANINE;

EID: 34250746403     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700020q     Document Type: Article
Times cited : (43)

References (41)
  • 1
    • 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
  • 2
    • 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.
    • (1990) J. Chromatogr. Sci , vol.28 , pp. 230-235
    • Pelz, N.1    Dempster, N.M.2    Shore, P.R.3
  • 4
    • 0025048644 scopus 로고
    • Carcinogenicity of 1,3-butadiene in C57BL/6 x C3H F1 mice at low exposure concentrations
    • Melnick, R. L., Huff, J., Chou, B. J., and Miller, R. A. (1990) Carcinogenicity of 1,3-butadiene in C57BL/6 x C3H F1 mice at low exposure concentrations, Cancer Res. 50, 6592-6599.
    • (1990) Cancer Res , vol.50 , pp. 6592-6599
    • Melnick, R.L.1    Huff, J.2    Chou, B.J.3    Miller, R.A.4
  • 6
    • 0028580221 scopus 로고    scopus 로고
    • Ward, J. B. Jr., Ammenheuser, M. M., Bechtold, W. E., Whorton, E. B. Jr., and Legator, M. S. (1994) hprt mutant lymphocyte frequencies in workers at a 1,3-butadiene production plant. Environ. Health Perspect. 102 (Suppl. 9), 79-85.
    • Ward, J. B. Jr., Ammenheuser, M. M., Bechtold, W. E., Whorton, E. B. Jr., and Legator, M. S. (1994) hprt mutant lymphocyte frequencies in workers at a 1,3-butadiene production plant. Environ. Health Perspect. 102 (Suppl. 9), 79-85.
  • 7
    • 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
  • 8
    • 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
  • 9
    • 0023262639 scopus 로고
    • Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/ carcinogenicity study in rats
    • Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987) Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/ carcinogenicity study in rats, Am. Ind. Hyg. Assoc. J. 48, 407-413.
    • (1987) Am. Ind. Hyg. Assoc. J , vol.48 , pp. 407-413
    • Owen, P.E.1    Glaister, J.R.2    Gaunt, I.F.3    Pullinger, D.H.4
  • 11
    • 0023919289 scopus 로고
    • Genotoxic properties of 1,3-butadiene
    • de Meester, C. (1988) Genotoxic properties of 1,3-butadiene, Mutat. Res. 195, 273-281.
    • (1988) Mutat. Res , vol.195 , pp. 273-281
    • de Meester, C.1
  • 12
    • 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.
    • (1982) Xenobiotica , vol.12 , pp. 137-144
    • Malvoisin, E.1    Roberfroid, M.2
  • 13
    • 0030605125 scopus 로고    scopus 로고
    • Metabolism of 1,3-butadiene: Inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice
    • 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.
    • (1996) Toxicology , vol.113 , pp. 306-309
    • Himmelstein, M.W.1    Turner, M.J.2    Asgharian, B.3    Bond, J.A.4
  • 14
    • 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
  • 15
    • 0025766839 scopus 로고
    • 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro
    • Sasiadek, M., Norppa, H., and Sorsa, M. (1991) 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro, Mutat. Res. 261, 117-121.
    • (1991) Mutat. Res , vol.261 , pp. 117-121
    • Sasiadek, M.1    Norppa, H.2    Sorsa, M.3
  • 16
    • 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.
    • (1994) Carcinogenesis , vol.15 , pp. 713-717
    • Cochrane, J.E.1    Skopek, T.R.2
  • 17
    • 0015242771 scopus 로고
    • Inactivation of the T7 coliphage by the diepoxybutane stereoisomers
    • Verly, W. G., Brakier, L., and Feit, P. W. (1971) Inactivation of the T7 coliphage by the diepoxybutane stereoisomers, Biochim. Biopliys. Acta 228, 400-406.
    • (1971) Biochim. Biopliys. Acta , vol.228 , pp. 400-406
    • Verly, W.G.1    Brakier, L.2    Feit, P.W.3
  • 18
    • 0014488988 scopus 로고
    • Induction of chromosomal aberrations and mutations with isomeric forms of L-threitol-1,4-bismethanesulfonate in plant materials
    • Matagne, R. (1969) Induction of chromosomal aberrations and mutations with isomeric forms of L-threitol-1,4-bismethanesulfonate in plant materials, Mutat. Res. 7, 241-247.
    • (1969) Mutat. Res , vol.7 , pp. 241-247
    • Matagne, R.1
  • 19
    • 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
  • 20
    • 34250715545 scopus 로고    scopus 로고
    • Kim, M. Y., Park, S., Tretyakova, N. Y., and Wogan, G. N. (2007) Mutagenesis of 1,2,3,4-diepoxybutane in the supF gene: role of stereochemistry, Chem. Res. Toxicol. (in press).
    • Kim, M. Y., Park, S., Tretyakova, N. Y., and Wogan, G. N. (2007) Mutagenesis of 1,2,3,4-diepoxybutane in the supF gene: role of stereochemistry, Chem. Res. Toxicol. (in press).
  • 21
    • 0014202447 scopus 로고
    • Interstrand cross-linking of DNA by difunctional alkylating agents
    • Lawley, P. D., and Brookes, P. (1967) Interstrand cross-linking of DNA by difunctional alkylating agents, J. Mol. Biol. 25, 143-160.
    • (1967) J. Mol. Biol , vol.25 , pp. 143-160
    • Lawley, P.D.1    Brookes, P.2
  • 22
    • 1342310594 scopus 로고    scopus 로고
    • Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane
    • Park, S., and Tretyakova, N. (2004) Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane, Chem. Res. Toxicol. 17, 129-136.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 129-136
    • Park, S.1    Tretyakova, N.2
  • 23
    • 0027403413 scopus 로고
    • Diepoxybutane cross-links DNA at 5′-GNC sequences
    • Millard, J. T., and White, M. M. (1993) Diepoxybutane cross-links DNA at 5′-GNC sequences, Biochemistry 32, 2120-2124.
    • (1993) Biochemistry , vol.32 , pp. 2120-2124
    • Millard, J.T.1    White, M.M.2
  • 24
    • 0029742311 scopus 로고    scopus 로고
    • The 5′-GNC preference for mustard cross-linking is preserved in a restriction fragment
    • Millard, J. T., Luedtke, N. W., and Spencer, R. J. (1996) The 5′-GNC preference for mustard cross-linking is preserved in a restriction fragment, Anticancer Drug Des. 11, 485-492.
    • (1996) Anticancer Drug Des , vol.11 , pp. 485-492
    • Millard, J.T.1    Luedtke, N.W.2    Spencer, R.J.3
  • 25
    • 0035807064 scopus 로고    scopus 로고
    • Diepoxybutane and diepoxyoctane interstrand cross-linking of the 5S DNA nucleosomal core particle
    • Millard, J. T., and Wilkes, E. E. (2001) Diepoxybutane and diepoxyoctane interstrand cross-linking of the 5S DNA nucleosomal core particle. Biochemistry 40, 10677-10685.
    • (2001) Biochemistry , vol.40 , pp. 10677-10685
    • Millard, J.T.1    Wilkes, E.E.2
  • 26
    • 31844444630 scopus 로고    scopus 로고
    • The 5′-GNC site for DNA interstrand cross-linking is conserved for diepoxybutane stereoisomers
    • Millard, J. T., Hanly, T. C., Murphy, K., and Tretyakova, N. (2006) The 5′-GNC site for DNA interstrand cross-linking is conserved for diepoxybutane stereoisomers, Chem. Res. Toxicol. 19, 16-19.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 16-19
    • Millard, J.T.1    Hanly, T.C.2    Murphy, K.3    Tretyakova, N.4
  • 27
    • 26844432462 scopus 로고    scopus 로고
    • Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: Role of stereochemistry
    • 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.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14355-14365
    • Park, S.1    Anderson, C.2    Loeber, R.3    Seetharaman, M.4    Jones, R.5    Tretyakova, N.6
  • 28
    • 10844236473 scopus 로고    scopus 로고
    • Guanine-adenine cross-linking by 1,2,3,4-diepoxybutane: Potential basis for biological activity
    • Park, S., Hodge, J., Anderson, C., and Tretyakova, N. Y. (2004) Guanine-adenine cross-linking by 1,2,3,4-diepoxybutane: potential basis for biological activity, Chem. Res. Toxicol. 17, 1638-1651.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 1638-1651
    • Park, S.1    Hodge, J.2    Anderson, C.3    Tretyakova, N.Y.4
  • 29
    • 0346368322 scopus 로고    scopus 로고
    • Identification and characterization of a series of nucleoside adducts formed by the reaction of 2′-deoxyguanosine and 1,2,3,4-diepoxybutane under physiological conditions
    • Zhang, X. Y., and Elfarra, A. A. (2003) Identification and characterization of a series of nucleoside adducts formed by the reaction of 2′-deoxyguanosine and 1,2,3,4-diepoxybutane under physiological conditions, Chem. Res. Toxicol. 16, 1606-1615.
    • (2003) Chem. Res. Toxicol , vol.16 , pp. 1606-1615
    • Zhang, X.Y.1    Elfarra, A.A.2
  • 31
    • 0031921976 scopus 로고    scopus 로고
    • Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry
    • Tretyakova, N. Y., Chiang, S. Y., Walker, V. E., and Swenberg, J. A. (1998) Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry, J. Mass Spectrom. 33, 363-376.
    • (1998) J. Mass Spectrom , vol.33 , pp. 363-376
    • Tretyakova, N.Y.1    Chiang, S.Y.2    Walker, V.E.3    Swenberg, J.A.4
  • 32
    • 0344258432 scopus 로고    scopus 로고
    • Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene
    • Koc, H., Tretyakova, N. Y., Walker, V. E., Henderson, R. F., and Swenberg, J. A. (1999) Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene, Chem. Res. Toxicol. 12, 566-574.
    • (1999) Chem. Res. Toxicol , vol.12 , pp. 566-574
    • Koc, H.1    Tretyakova, N.Y.2    Walker, V.E.3    Henderson, R.F.4    Swenberg, J.A.5
  • 33
    • 0032976759 scopus 로고    scopus 로고
    • Persistence of N7-(2,3,4- trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene
    • Oe. T., Kambouris, S. J., Walker, V. E., Meng, Q., Recio, L., Wherli, S., Chaudhary, A. K., and Blair, I. A. (1999) Persistence of N7-(2,3,4- trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene, Chem. Res. Toxicol. 12, 247-257.
    • (1999) Chem. Res. Toxicol , vol.12 , pp. 247-257
    • Oe, T.1    Kambouris, S.J.2    Walker, V.E.3    Meng, Q.4    Recio, L.5    Wherli, S.6    Chaudhary, A.K.7    Blair, I.A.8
  • 34
    • 33751008084 scopus 로고    scopus 로고
    • Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2- deoxy-beta-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS
    • Matter, B., Malejka-Giganti, D., Csallany, A. S., and Tretyakova, N. (2006) Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2- deoxy-beta-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS, Nucleic Acids Res. 34, 5449-5460.
    • (2006) Nucleic Acids Res , vol.34 , pp. 5449-5460
    • Matter, B.1    Malejka-Giganti, D.2    Csallany, A.S.3    Tretyakova, N.4
  • 36
    • 0035018737 scopus 로고    scopus 로고
    • DNA adducts of 1,3-butadiene in humans: Relationships to exposure, GST genotypes, single-strand breaks, and cytogenetic end points
    • Zhao, C., Vodicka, P., Sram, R. J., and Hemminki, K. (2001) DNA adducts of 1,3-butadiene in humans: Relationships to exposure, GST genotypes, single-strand breaks, and cytogenetic end points, Environ. Mol. Mutagen. 37, 226-230.
    • (2001) Environ. Mol. Mutagen , vol.37 , pp. 226-230
    • Zhao, C.1    Vodicka, P.2    Sram, R.J.3    Hemminki, K.4
  • 37
    • 0344349003 scopus 로고    scopus 로고
    • Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7- guanine: A high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure
    • Koivisto, P., Kilpelainen, I., Rasanen, I., Adler, I. D., Pacchierotti, F., and Peltonen, K. (1999) Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7- guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure, Carcinogenesis 20, 1253-1259.
    • (1999) Carcinogenesis , vol.20 , pp. 1253-1259
    • Koivisto, P.1    Kilpelainen, I.2    Rasanen, I.3    Adler, I.D.4    Pacchierotti, F.5    Peltonen, K.6
  • 38
    • 33947105963 scopus 로고    scopus 로고
    • Metabolism of 1,3-butadiene to toxicologically relevant metabolites in single-exposed mice and rats
    • Filser, J. G., Hutzler, C., Meischner, V., Veereshwarayya, V., and Csanady, G. A. (2007) Metabolism of 1,3-butadiene to toxicologically relevant metabolites in single-exposed mice and rats, Chem.-Biol. Interact. 166, 93-103
    • (2007) Chem.-Biol. Interact , vol.166 , pp. 93-103
    • Filser, J.G.1    Hutzler, C.2    Meischner, V.3    Veereshwarayya, V.4    Csanady, G.A.5
  • 39
    • 9244249860 scopus 로고    scopus 로고
    • Analysis of diepoxide-specific cyclic N-terminal globin adducts in mice and rats after inhalation exposure to 1,3-butadiene
    • Boysen, G., Georgieva, N. I., Upton, P. B., Jayaraj, K., Li, Y., Walker, V. E., and Swenberg, J. A. (2004) Analysis of diepoxide-specific cyclic N-terminal globin adducts in mice and rats after inhalation exposure to 1,3-butadiene, Cancer Res. 64, 8517-8520.
    • (2004) Cancer Res , vol.64 , pp. 8517-8520
    • Boysen, G.1    Georgieva, N.I.2    Upton, P.B.3    Jayaraj, K.4    Li, Y.5    Walker, V.E.6    Swenberg, J.A.7
  • 40
    • 0035017926 scopus 로고    scopus 로고
    • Metabolism of butadiene monoxide by freshly isolated hepatocytes from mice and rats: Different partitioning between oxidative, hydrolytic, and conjugation pathways
    • Kemper, R. A., Krause, R. J., and Elfarra, A. A. (2001) Metabolism of butadiene monoxide by freshly isolated hepatocytes from mice and rats: different partitioning between oxidative, hydrolytic, and conjugation pathways, Drug Metab. Dispos. 29, 830-836.
    • (2001) Drug Metab. Dispos , vol.29 , pp. 830-836
    • Kemper, R.A.1    Krause, R.J.2    Elfarra, A.A.3
  • 41
    • 0035369198 scopus 로고    scopus 로고
    • Cellular and molecular basis for species, sex and tissue differences in 1,3-butadiene metabolism
    • Elfarra, A. A., Krause, R. J., and Kemper, R. A. (2001) Cellular and molecular basis for species, sex and tissue differences in 1,3-butadiene metabolism, Chem.-Biol. Interact. 135-136, 239-248.
    • (2001) Chem.-Biol. Interact , vol.135-136 , pp. 239-248
    • Elfarra, A.A.1    Krause, R.J.2    Kemper, R.A.3


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