메뉴 건너뛰기




Volumn 19, Issue 12, 2006, Pages 1611-1618

Biomarkers for isocyanate exposure: Synthesis of isocyanate DNA adducts

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROPHENYL ISOCYANATE; 4 TOLYL ISOCYANATE; BIOLOGICAL MARKER; DEOXYADENOSINE; DEOXYCYTIDINE; DEOXYGUANOSINE; ISOCYANIC ACID DERIVATIVE; XENOBIOTIC AGENT;

EID: 33845809152     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0600853     Document Type: Article
Times cited : (21)

References (36)
  • 1
    • 84983108547 scopus 로고
    • (Hutzinger, O., Ed.), Springer-Verlag, Heidelberg, Germany
    • Brochhagen, F. (1991) In The Handbook of Environmental Chemistry (Hutzinger, O., Ed.) Vol. 3, part G., pp 1-95, Springer-Verlag, Heidelberg, Germany.
    • (1991) The Handbook of Environmental Chemistry , vol.3 , Issue.PART G , pp. 1-95
    • Brochhagen, F.1
  • 2
    • 33845751390 scopus 로고    scopus 로고
    • Berufsgenossenschaften der chemischen Industrie, BG-Chemie, Heidelberg, Germany
    • Berufsgenossenschaften der chemischen Industrie, (1997) Toxikologische Bewertung: 4-Chlorphenylisocyanat, Nr. 78, pp 1-23 BG-Chemie, Heidelberg, Germany.
    • (1997) Toxikologische Bewertung: 4-Chlorphenylisocyanat , vol.78 , pp. 1-23
  • 4
    • 0027050667 scopus 로고
    • Mercapturic acids, protein adducts, and DNA adducts as biomarkers of electrophilic chemicals
    • van Welie, R. T. H., van Dijck, R. G. J. M., Vermeulen, N. P. E., and van Sittert, N. J. (1992) Mercapturic acids, protein adducts, and DNA adducts as biomarkers of electrophilic chemicals. Crit. Rev. Toxicol. 22, 271-306.
    • (1992) Crit. Rev. Toxicol. , vol.22 , pp. 271-306
    • Van Welie, R.T.H.1    Van Dijck, R.G.J.M.2    Vermeulen, N.P.E.3    Van Sittert, N.J.4
  • 5
    • 0031803283 scopus 로고    scopus 로고
    • Pathomechanisms and pathophysiology of isocyanate-induced diseases-summary of present knowledge
    • Raulf-Heimsoth, M., and Baur, X. (1998) Pathomechanisms and pathophysiology of isocyanate-induced diseases-summary of present knowledge. Am. J. Ind. Med. 324, 137-143.
    • (1998) Am. J. Ind. Med. , vol.324 , pp. 137-143
    • Raulf-Heimsoth, M.1    Baur, X.2
  • 7
    • 0000037422 scopus 로고
    • Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons
    • (Cooper, C.S., and Graver, P.L., Eds.), Springer-Verlag, Heidelberg, Germany
    • Beland, F. A., and Kadlubar, F. F. (1990) Metabolic Activation and DNA Adducts of Aromatic Amines and Nitroaromatic Hydrocarbons. In Chemical Carcinogenesis and Mutagenesis I (Cooper, C.S., and Graver, P.L., Eds.) pp 267-325, Springer-Verlag, Heidelberg, Germany.
    • (1990) Chemical Carcinogenesis and Mutagenesis I , pp. 267-325
    • Beland, F.A.1    Kadlubar, F.F.2
  • 8
    • 0035209214 scopus 로고    scopus 로고
    • Carcinogenic risk of toluene diisocyanate and 4,4′- methylenediphenyl diisocyanate: Epidemiological and experimental evidence
    • Bolognesi, C., Baur, X., Marczynski, B., Norppa, H., Sepai, O., and Sabbioni, G. (2001) Carcinogenic risk of toluene diisocyanate and 4,4′-methylenediphenyl diisocyanate: epidemiological and experimental evidence. Crit. Rev. Toxicol. 31, 737-772.
    • (2001) Crit. Rev. Toxicol. , vol.31 , pp. 737-772
    • Bolognesi, C.1    Baur, X.2    Marczynski, B.3    Norppa, H.4    Sepai, O.5    Sabbioni, G.6
  • 9
    • 0023915285 scopus 로고
    • Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo
    • Ringe, D., Turesky, R. J., Skipper, P. L., and Tannenbaum, S. R. (1988) Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo. Chem. Res. Toxicol. I, 22-24.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 22-24
    • Ringe, D.1    Turesky, R.J.2    Skipper, P.L.3    Tannenbaum, S.R.4
  • 10
    • 0036756016 scopus 로고    scopus 로고
    • Biomonitoring of arylamines and nitroarenes
    • Sabbioni, G., and Jones, C. R. (2002) Biomonitoring of arylamines and nitroarenes. Biomarkers 7, 347-421.
    • (2002) Biomarkers , vol.7 , pp. 347-421
    • Sabbioni, G.1    Jones, C.R.2
  • 12
    • 0035666727 scopus 로고    scopus 로고
    • Synthesis of adducts with amino acids as potential dosimeters for the biomonitoring of humans exposed to toluenediisocyanate
    • Sabbioni, G., Hartley, R., and Schneider, S. (2001) Synthesis of adducts with amino acids as potential dosimeters for the biomonitoring of humans exposed to toluenediisocyanate. Chem. Res. Toxicol. 14, 1573-1583.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1573-1583
    • Sabbioni, G.1    Hartley, R.2    Schneider, S.3
  • 14
    • 0002785296 scopus 로고    scopus 로고
    • Synthesis and analysis of DNA adducts of arylamines
    • Beyerbach, A., Farmer, P. B., and Sabbioni, G. (1996) Synthesis and analysis of DNA adducts of arylamines. Biomarkers 1, 9-20.
    • (1996) Biomarkers , vol.1 , pp. 9-20
    • Beyerbach, A.1    Farmer, P.B.2    Sabbioni, G.3
  • 15
    • 0030034422 scopus 로고    scopus 로고
    • Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke
    • Marques, M. M., Mourato, L. L., Santos, M. A., and Beland, F. A. (1996) Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke. Chem. Res. Toxicol. 9, 99-108.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 99-108
    • Marques, M.M.1    Mourato, L.L.2    Santos, M.A.3    Beland, F.A.4
  • 16
    • 0030819637 scopus 로고    scopus 로고
    • Effect of substitution site upon the oxidation potentials of alkylanilines, the mutagenicities of N-hydroxyalkylanilines, and the conformations of alkylaniline-DNA adducts
    • Marques, M. M., Mourato, L. L. G., Amorim, M. T., Santos, M. A. Melchior, W. B., Jr., and Beland, F. A. (1997) Effect of substitution site upon the oxidation potentials of alkylanilines, the mutagenicities of N-hydroxyalkylanilines, and the conformations of alkylaniline-DNA adducts. Chem. Res. Toxicol. 10, 1266-1274.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1266-1274
    • Marques, M.M.1    Mourato, L.L.G.2    Amorim, M.T.3    Santos, M.A.4    Melchior Jr., W.B.5    Beland, F.A.6
  • 17
    • 0142169953 scopus 로고    scopus 로고
    • Identification of DNA adducts using HPLC/MS/MS following in vitro and in vivo experiments with arylamines and nitroarenes
    • Jones, C. R., and Sabbioni, G. (2003) Identification of DNA adducts using HPLC/MS/MS following in vitro and in vivo experiments with arylamines and nitroarenes. Chem. Res. Toxicol. 16, 1251-1263.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1251-1263
    • Jones, C.R.1    Sabbioni, G.2
  • 18
    • 0010569433 scopus 로고
    • Synthesis and properties of N-carbamoyl derivatives of cytosine, cytidine, uracil and thymine
    • Dutta, S. P., and Chheda, G. B. (1980) Synthesis and properties of N-carbamoyl derivatives of cytosine, cytidine, uracil and thymine. J. Carbohydr., Nucleosides, Nucleotides 7, 217-240.
    • (1980) J. Carbohydr., Nucleosides, Nucleotides , vol.7 , pp. 217-240
    • Dutta, S.P.1    Chheda, G.B.2
  • 19
    • 0024543937 scopus 로고
    • Isolation of methyl-carbamoyl-adducts of adenine and cytosine following in vitro reaction of methyl isocyanate with calf thymus DNA
    • Segal, A., Solomon, J. J., and Li, F. J. (1989) Isolation of methyl-carbamoyl-adducts of adenine and cytosine following in vitro reaction of methyl isocyanate with calf thymus DNA. Chem.-Biol. Interact. 69, 359-372.
    • (1989) Chem.-Biol. Interact. , vol.69 , pp. 359-372
    • Segal, A.1    Solomon, J.J.2    Li, F.J.3
  • 20
    • 0014736878 scopus 로고
    • The reaction of phenyl isocyanate with purines, pyrimidines and deoxyribonucleic acid
    • Jones, A. S., and Warren, J. H. (1970) The reaction of phenyl isocyanate with purines, pyrimidines and deoxyribonucleic acid. Tetrahedron 26, 791-794.
    • (1970) Tetrahedron , vol.26 , pp. 791-794
    • Jones, A.S.1    Warren, J.H.2
  • 21
    • 0025085881 scopus 로고
    • Characterization and genotoxicity of DNA adducts caused by 2-naphthyl isocyanate
    • Tamura, N., Aoki, K., and Lee, M. S. (1990) Characterization and genotoxicity of DNA adducts caused by 2-naphthyl isocyanate. Carcinogenesis II, 2009-2014.
    • (1990) Carcinogenesis , vol.2 , pp. 2009-2014
    • Tamura, N.1    Aoki, K.2    Lee, M.S.3
  • 22
    • 0026739143 scopus 로고
    • Selective reactivities of isocyanates towards DNA bases and genotoxicity of methylcarbamoylation of DNA
    • Tamura, N., Aoki, K., and Lee, M. S. (1992) Selective reactivities of isocyanates towards DNA bases and genotoxicity of methylcarbamoylation of DNA. Mutat. Res. 283, 97-106.
    • (1992) Mutat. Res. , vol.283 , pp. 97-106
    • Tamura, N.1    Aoki, K.2    Lee, M.S.3
  • 23
    • 0028721094 scopus 로고
    • DNA adducts of lactones, sultones, acylating agents and acrylic compounds
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publications No. 125., International Agency for Research on Cancer, Lyon, France
    • Solomon, J. J. (1994) DNA Adducts of Lactones, Sultones, Acylating Agents and Acrylic Compounds. In DNA Adducts: Identificaton and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publications No. 125., pp 179-198, International Agency for Research on Cancer, Lyon, France.
    • (1994) DNA Adducts: Identificaton and Biological Significance , pp. 179-198
    • Solomon, J.J.1
  • 24
    • 0028987259 scopus 로고
    • 32P-postlabeling analysis of DNA adducts formed in vitro and in rat skin by methylenediphenyl-4,4′-diisocyanate (MDI)
    • 32P-postlabeling analysis of DNA adducts formed in vitro and in rat skin by methylenediphenyl-4,4′-diisocyanate (MDI). Toxicol. Lett. 76, 17-26.
    • (1995) Toxicol. Lett. , vol.76 , pp. 17-26
    • Vock, E.H.1    Cantoreggi, S.2    Gupta, R.C.3    Lutz, W.K.4
  • 25
    • 0036168651 scopus 로고    scopus 로고
    • Glutathione-dependent metabolism of the antitumor agent sulofenur. Evidence for the formation of p-chlorophenyl isocyanate as a reactive intermediate
    • Jochheim, C. M., Davis, M. R., Baillie, K. M., Ehlhardt, W. J., and Baillie, T. A. (2002) Glutathione-dependent metabolism of the antitumor agent sulofenur. Evidence for the formation of p-chlorophenyl isocyanate as a reactive intermediate. Chem. Res. Toxicol 15, 240-248.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 240-248
    • Jochheim, C.M.1    Davis, M.R.2    Baillie, K.M.3    Ehlhardt, W.J.4    Baillie, T.A.5
  • 26
    • 0026549493 scopus 로고
    • Carbamoylation reactions of N-methyl-N′-aryl-N-nitrosoureas and corresponding phenyl isocyanates to 5′-amino-5′-deoxythymidine: Importance of carbamoylation in mouse skin carcinogenic processes
    • Yano, K. (1992) Carbamoylation reactions of N-methyl-N′-aryl-N- nitrosoureas and corresponding phenyl isocyanates to 5′-amino-5′- deoxythymidine: importance of carbamoylation in mouse skin carcinogenic processes. Carcinogenesis 13, 699-702.
    • (1992) Carcinogenesis , vol.13 , pp. 699-702
    • Yano, K.1
  • 27
    • 0025963771 scopus 로고
    • Biotransformation of methyl isocyanate in the rat. Evidence for glutathione conjugation as a major pathway of metabolism and implications for isocyanate-mediated toxicities
    • Slatter, J. G., Rashed, M. S., Pearson, P. G., Han, D. H., and Baillie, T. A. (1991) Biotransformation of methyl isocyanate in the rat. Evidence for glutathione conjugation as a major pathway of metabolism and implications for isocyanate-mediated toxicities. Chem. Res. Toxicol. 4, 157-161.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 157-161
    • Slatter, J.G.1    Rashed, M.S.2    Pearson, P.G.3    Han, D.H.4    Baillie, T.A.5
  • 28
    • 0026056412 scopus 로고
    • Carbamoylation of peptides and proteins in vitro by S-(N-methylcarbamoyl) glutathione and S-(N-methylcarbamoyl)cysteine, two electrophilic S-linked conjugates of methyl isocyanate
    • Pearson, P. G., Slatter, J. G., Rashed, M. S., Han, D. H., and Baillie, T. A. (1991) Carbamoylation of peptides and proteins in vitro by S-(N-methylcarbamoyl)glutathione and S-(N-methylcarbamoyl)cysteine, two electrophilic S-linked conjugates of methyl isocyanate. Chem. Res. Toxicol. 4, 436-444.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 436-444
    • Pearson, P.G.1    Slatter, J.G.2    Rashed, M.S.3    Han, D.H.4    Baillie, T.A.5
  • 29
    • 0030909675 scopus 로고    scopus 로고
    • Formation, solvolysis, and transcarbamoylation reactions of bis(S-glutathionyl) adducts of 2,4- And 2,6-diisocyanatotoluene
    • Day, B. W., Jin, R., Basalyga, D. M., Kramarik, J. A., and Karol, M. H. (1997) Formation, solvolysis, and transcarbamoylation reactions of bis(S-glutathionyl) adducts of 2,4- and 2,6-diisocyanatotoluene. Chem. Res. Toxicol. 10, 424-431.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 424-431
    • Day, B.W.1    Jin, R.2    Basalyga, D.M.3    Kramarik, J.A.4    Karol, M.H.5
  • 30
    • 0031855953 scopus 로고    scopus 로고
    • Synthesis and spectroscopic characterization of 4-chlorophenyl isocyanate (= 1-chloro-4-isocyanatobenzene) adducts with amino acids as potential dosimeters for the biomonitoring of isocyanate exposure
    • Möller, M., Henschler, D., and Sabbioni, G. (1998) Synthesis and spectroscopic characterization of 4-chlorophenyl isocyanate (= 1-chloro-4-isocyanatobenzene) adducts with amino acids as potential dosimeters for the biomonitoring of isocyanate exposure. Helv. Chim. Acta 81, 1254-1263.
    • (1998) Helv. Chim. Acta , vol.81 , pp. 1254-1263
    • Möller, M.1    Henschler, D.2    Sabbioni, G.3
  • 31
    • 21544453857 scopus 로고    scopus 로고
    • Reactions of 4-methylphenyl isocyanate with amino acids
    • Sabbioni, G., Lamb, J. H., Farmer, P. B., and Sepai, O. (1997) Reactions of 4-methylphenyl isocyanate with amino acids. Biomarkers 2, 223-232.
    • (1997) Biomarkers , vol.2 , pp. 223-232
    • Sabbioni, G.1    Lamb, J.H.2    Farmer, P.B.3    Sepai, O.4
  • 33
    • 0003909854 scopus 로고
    • John Wiley & Sons, Chichester, England
    • Günther, H. (1995) NMR Spectroscopy, John Wiley & Sons, Chichester, England.
    • (1995) NMR Spectroscopy
    • Günther, H.1
  • 36
    • 0003591530 scopus 로고
    • Chemical modification of deoxyribonucleic acids: A direct study by carbon-13 nuclear magnetic resonance spectroscopy
    • Chang, C. J., DaSilva Gomes, J., and Byrn, S. R. (1983) Chemical modification of deoxyribonucleic acids: A direct study by carbon-13 nuclear magnetic resonance spectroscopy. J. Org. Chem. 48, 5151-5160.
    • (1983) J. Org. Chem. , vol.48 , pp. 5151-5160
    • Chang, C.J.1    DaSilva Gomes, J.2    Byrn, S.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.