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Volumn 22, Issue 6, 2009, Pages 1163-1171

Mass spectral analyses of hydroxymethylvinyl ketone-hemoglobin adducts formed after in vivo exposure of sprague-dawley rats to 3-butene-1,2-diol

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 3 BUTENE 1,2 DIOL; BUTANE; GLYCOSYLATED HEMOGLOBIN; HEMOGLOBIN A2; HYDROXYMETHYLVINYLKETONE; KETONE DERIVATIVE; PEPTIDE; UNCLASSIFIED DRUG;

EID: 67449085960     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900079q     Document Type: Article
Times cited : (4)

References (30)
  • 1
    • 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. (Pubitemid 27357701)
    • (1997) Drug Metabolism and Disposition , vol.25 , Issue.8 , pp. 1013-1015
    • Krause, R.J.1    Sharer, J.E.2    Elfarra, A.A.3
  • 2
    • 0028018206 scopus 로고
    • Species differences in urinary butadiene metabolites: Comparisons of metabolite ratios between mice, rats, and humans
    • DOI 10.1006/taap.1994.1137
    • Bechtold, W. E., Strunk, M. R., Chang, I. Y., Ward, J. B., and Henderson, R. F. (1994) Species differences in urinary butadiene metabolites: Comparisons of metabolite ratios between mice, rats, and humans. Toxicol. Appl. Pharmacol. 127, 44-49. (Pubitemid 24248632)
    • (1994) Toxicology and Applied Pharmacology , vol.127 , Issue.1 , pp. 44-49
    • Bechtold, W.E.1    Strunk, M.R.2    Chang, I.-Y.3    Ward Jr., J.B.4    Henderson, R.F.5
  • 3
    • 3042842515 scopus 로고    scopus 로고
    • Species and tissue differences in the toxicity of 3-butene-1,2-diol in male Sprague-Dawley rats and B6C3F1 mice
    • DOI 10.1093/toxsci/kfh156
    • Sprague, C. L., Phillips, L. A., Young, K. M., and Elfarra, A. A. (2004) Species and tissue differences in the toxicity of 3-butene-1,2-diol in male Sprague-Dawley rats and B6C3F1 mice. Toxicol. Sci. 80, 3-13. (Pubitemid 38967391)
    • (2004) Toxicological Sciences , vol.80 , Issue.1 , pp. 3-13
    • Sprague, C.L.1    Phillips, L.A.2    Young, K.M.3    Elfarra, A.A.4
  • 7
    • 0031716137 scopus 로고    scopus 로고
    • Metabolism of 3-butene-1,2-diol in B6C3F1 mice: Evidence for involvement of alcohol dehydrogenase and cytochrome P450
    • Kemper, R. A., Elfarra, A. A., and Myers, S. R. (1998) Metabolism of 3-butene-1,2-diol in B6C3F1 mice: Evidence for involvement of alcohol dehydrogenase and cytochrome P450. Drug Metab. Dispos. 26, 914-920. (Pubitemid 28452059)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.9 , pp. 914-920
    • Kemper, R.A.1    Elfarra, A.A.2    Myers, S.R.3
  • 8
    • 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. (Pubitemid 27357701)
    • (1997) Drug Metabolism and Disposition , vol.25 , Issue.8 , pp. 1013-1015
    • Krause, R.J.1    Sharer, J.E.2    Elfarra, A.A.3
  • 9
    • 0031716137 scopus 로고    scopus 로고
    • Metabolism of 3-butene-1,2-diol in B6C3F1 mice: Evidence for involvement of alcohol dehydrogenase and cytochrome P450
    • Kemper, R. A., Elfarra, A. A., and Myers, S. R. (1998) Metabolism of 3-butene-1,2-diol in B6C3F1 mice: Evidence for involvement of alcohol dehydrogenase and cytochrome P450. Drug Metab. Dispos. 26, 914-920. (Pubitemid 28452059)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.9 , pp. 914-920
    • Kemper, R.A.1    Elfarra, A.A.2    Myers, S.R.3
  • 10
    • 0029958579 scopus 로고    scopus 로고
    • Oxidation of 3-butene-1,2-diol by alcohol dehydrogenase
    • DOI 10.1021/tx960090e
    • Kemper, R. A., and Elfarra, A. A. (1996) Oxidation of 3-butene-1,2-diol by alcohol dehydrogenase. Chem. Res. Toxicol. 96, 1127-1134. (Pubitemid 26347965)
    • (1996) Chemical Research in Toxicology , vol.9 , Issue.7 , pp. 1127-1134
    • Kemper, R.A.1    Elfarra, A.A.2
  • 11
    • 0035663082 scopus 로고    scopus 로고
    • Hydroxymethylvinyl ketone: A reactive michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome p450s and mouse, rat, and human liver microsomes
    • DOI 10.1021/tx010117g
    • Krause, R. J., Kemper, R. A., and Elfarra, A. A. (2001) Hydroxymethylvinyl ketone: A reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes. Chem. Res. Toxicol. 14, 1590-1595. (Pubitemid 34016622)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.12 , pp. 1590-1595
    • Krause, R.J.1    Kemper, R.A.2    Elfarra, A.A.3
  • 12
    • 33947171447 scopus 로고    scopus 로고
    • Mass spectral analyses of hemoglobin adducts formed after in vitro exposure of erythrocytes to hydroxymethylvinyl ketone
    • DOI 10.1016/j.cbi.2006.04.012, PII S0009279706000937
    • Barshteyn, N., Krause, R. J., and Elfarra, A. A. (2007) Mass spectral analyses of hemoglobin adducts formed after in vitro exposure of erythrocytes to hydroxymethylvinyl ketone. Chem.-Biol. Interact. 166, 176-181. (Pubitemid 46413207)
    • (2007) Chemico-Biological Interactions , vol.166 , Issue.1-3 , pp. 176-181
    • Barshteyn, N.1    Krause, R.J.2    Elfarra, A.A.3
  • 13
    • 3042768116 scopus 로고    scopus 로고
    • Mercapturic acid urinary metabolites of 3-butene-1,2-diol as in vivo evidence for the formation of hydroxymethylvinyl ketone in mice and rats
    • DOI 10.1021/tx049949f
    • Sprague, C. L., and Elfarra, A. A. (2004) Mercapturic acid urinary metabolites of 3-butene-1,2-diol as in vivo evidence for the formation of hydroxymethylvinyl ketone in mice and rats. Chem. Res. Toxicol. 17, 819-826. (Pubitemid 38856343)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.6 , pp. 819-826
    • Sprague, C.L.1    Elfarra, A.A.2
  • 14
    • 67449083759 scopus 로고    scopus 로고
    • Formation of mono- and bis-Michael adducts by the reaction of nucleophilic amino acids with hydroxymethylvinyl ketone, a reactive metabolite of 1,3-butadiene
    • DOI: 10.1021/tx900006b
    • Barshteyn, N., and Elfarra, A. A. (2009) Formation of mono- and bis-Michael adducts by the reaction of nucleophilic amino acids with hydroxymethylvinyl ketone, a reactive metabolite of 1,3-butadiene. Chem. Res. Toxicol. DOI: 10.1021/tx900006b.
    • (2009) Chem. Res. Toxicol.
    • Barshteyn, N.1    Elfarra, A.A.2
  • 16
    • 0027467032 scopus 로고
    • A simplified methodology for quantitation of butadiene metabolites: Application to the study of 1,3-butadiene metabolism by rat liver microsomes
    • Cheng, X., and Ruth, J. A. (1993) A simplified methodology for quantitation of butadiene metabolites: Application to the study of 1,2-butadiene metabolism by rat liver microsomes. Drug Metab. Dispos. 21, 121-124. (Pubitemid 23052231)
    • (1993) Drug Metabolism and Disposition , vol.21 , Issue.1 , pp. 121-124
    • Cheng, X.1    Ruth, J.A.2
  • 18
    • 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
    • DOI 10.1006/taap.1996.0328
    • Boogard, 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. (Pubitemid 27046388)
    • (1996) Toxicology and Applied Pharmacology , vol.141 , Issue.2 , pp. 617-627
    • Boogaard, P.J.1    Bond, J.A.2
  • 20
    • 1542375854 scopus 로고    scopus 로고
    • 14C]-butadiene
    • DOI 10.1016/j.cbi.2004.01.002, PII S0009279704000043
    • Booth, E. D., Kilgour, J. D., and Watson, W. P. (2004) Dose responses for the formation of hemoglobin adducts and urinary metabolites in rats and mice exposed by inhalation to low concentrations of 1,3-[2,3-14C]-butadiene. Chem.-Biol. Interact. 147, 213-232. (Pubitemid 38315027)
    • (2004) Chemico-Biological Interactions , vol.147 , Issue.2 , pp. 213-232
    • Booth, E.D.1    Kilgour, J.D.2    Watson, W.P.3
  • 21
    • 0000894377 scopus 로고
    • The Rupe and Meyer-Schuster rearrangements
    • Swaminathan, S., and Narayanan, K. V. (1971) The Rupe and Meyer-Schuster rearrangements. Chem. Rev. 71, 429-438.
    • (1971) Chem. Rev. , vol.71 , pp. 429-438
    • Swaminathan, S.1    Narayanan, K.V.2
  • 22
    • 53549094137 scopus 로고    scopus 로고
    • Detection of multiple globin monoadducts and cross-links after in vitro exposure of rat erythrocytes to S-(1,2-dichlorovinyl)-L-cysteine sulfoxide and after in vivo treatment of rats with S-(1,2-dichlorovinyl)-L-cysteine sulfoxide
    • Barshteyn, N., and Elfarra, A. A. (2008) Detection of multiple globin monoadducts and cross-links after in vitro exposure of rat erythrocytes to S-(1,2-dichlorovinyl)-L-cysteine sulfoxide and after in vivo treatment of rats with S-(1,2-dichlorovinyl)-L-cysteine sulfoxide. Chem. Res. Toxicol. 21, 1716-1725.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1716-1725
    • Barshteyn, N.1    Elfarra, A.A.2
  • 23
    • 0033696728 scopus 로고    scopus 로고
    • A comprehensive structural analysis of hemoglobin adducts formed after in vitro exposure of erythrocytes to butadiene monoxide
    • DOI 10.1021/tx000151f
    • Moll, T. S., and Elfarra, A. A. (2000) A comprehensive structural analysis of hemoglobin adducts formed after in vitro exposure of erythrocytes to butadiene monoxide. Chem. Res. Toxicol. 13, 1103-1113. (Pubitemid 30954095)
    • (2000) Chemical Research in Toxicology , vol.13 , Issue.11 , pp. 1103-1113
    • Moll, T.S.1    Harms, A.C.2    Elfarra, A.A.3
  • 24
    • 0027787492 scopus 로고
    • Mass spectrometric analysis of rat hemoglobin by FAB-overlapping. Primary structure of the alpha-major and of four beta constitutive chains
    • DOI 10.1016/0020-711X(88)90329-1
    • Ferranti, P., Carbone, V., Sannolo, N., Fiume, I., and Malorni, A. (1993) Mass spectrometric analysis of rat hemoglobin by FAB-overlapping: primary structure of the R-major and of four β constitutive chains. Int. J. Biochem. 25, 1943-1950. (Pubitemid 2027497)
    • (1993) INT.J.BIOCHEM. , vol.25 , Issue.12 , pp. 1943-1950
    • Ferranti, P.1    Carbone, V.2    Sannolo, N.3    Fiume, I.4    Malorni, A.5
  • 25
    • 0029035314 scopus 로고
    • Stereoselective catalysis of a retro-Michael reaction by class mu glutathione transferases. Consequences for the internal distribution of products in the active site
    • Chen, J., and Armstrong, R. N. (1995) Stereoselective catalysis of a retro-Michael reaction by class mu glutathione transferases. Consequences for the internal distribution of products in the active site. Chem. Res. Toxicol. 8, 580-585.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 580-585
    • Chen, J.1    Armstrong, R.N.2
  • 26
    • 0037347349 scopus 로고    scopus 로고
    • Identification of intermediate pathways of 4-hydroxynonenal metabolism in the rat
    • DOI 10.1021/tx025671k
    • Alary, J., Fernandez, Y., Debrauwer, L., Perdu, E., and Gueraud, F. (2003) Identification of intermediate pathways of 4-hydroxynonenal metabolism in the rat. Chem. Res. Toxicol. 16, 320-327. (Pubitemid 36378133)
    • (2003) Chemical Research in Toxicology , vol.16 , Issue.3 , pp. 320-327
    • Alary, J.1    Fernandez, Y.2    Debrauwer, L.3    Perdu, E.4    Gueraud, F.5
  • 27
    • 0034057281 scopus 로고    scopus 로고
    • Disulfiram generates a stable N,N-diethylcarbamoyl adduct on Cys-125 of rat hemoglobin β-chains in vivo
    • DOI 10.1021/tx990191n
    • Erve, J. C. L., Jensen, O. N., Valentine, H. S., Amarnath, V., and Valentine, W. M. (2000) Disulfiram generates a stable N,N-diethylcarbamoyl adduct on Cys-125 of rat hemoglobin β-chains in vivo. Chem. Res. Toxicol. 13, 237-244. (Pubitemid 30241649)
    • (2000) Chemical Research in Toxicology , vol.13 , Issue.4 , pp. 237-244
    • Erve, J.C.L.1    Jensen, O.N.2    Valentine, H.S.3    Amarnath, V.4    Valentine, W.M.5
  • 29
    • 25144518337 scopus 로고    scopus 로고
    • Characterization of adducts formed between human serum albumin and the butadiene metabolite epoxybutanediol
    • DOI 10.1002/rcm.2086
    • Lindh, C. H., Kristiansson, M. H., Berg-Andersson, U. A., and Cohen, A. S. (2005) Characterization of adducts formed between human serum albumin and the butadiene metabolite epoxybutanediol. Rapid Commun. Mass Spectrom. 19, 2488-2496. (Pubitemid 41338590)
    • (2005) Rapid Communications in Mass Spectrometry , vol.19 , Issue.18 , pp. 2488-2496
    • Lindh, C.H.1    Kristiansson, M.H.2    Berg-Andersson, U.A.3    Cohen, A.S.4
  • 30
    • 0033938539 scopus 로고    scopus 로고
    • Biomarkers of exposure to 1,3-butadiene as a basis for cancer risk assessment
    • van Sittert, N. J., Megens, H. J. J. J., Watson, W. P., and Boogaard, P. J. (2000) Biomarkers of exposure to 1,3-butadiene as a basis for cancer risk assessment. Toxicol. Sci. 56, 189-202. (Pubitemid 30441479)
    • (2000) Toxicological Sciences , vol.56 , Issue.1 , pp. 189-202
    • Van Sittert, N.J.1    Megens, H.J.J.J.2    Watson, W.P.3    Boogaard, P.J.4


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