메뉴 건너뛰기




Volumn 19, Issue 3, 2006, Pages 341-350

Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE; DIAMINE; DIPHENYLMETHANE 4,4' DIISOCYANATE; DITHIOCARBAMIC ACID; HUMAN SERUM ALBUMIN; ISOCYANIC ACID DERIVATIVE; MECYSTEINE; TOLUENE; UREA DERIVATIVE;

EID: 33645462233     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050311t     Document Type: Article
Times cited : (16)

References (35)
  • 1
    • 0023580243 scopus 로고
    • Biochemistry of protein-isocyanate interactions: A comparison of the effects of aryl vs alkyl isocyanates
    • Brown, W. E., Green, A. H., Cedel, T. E., and Cairns, J. (1987) Biochemistry of protein-isocyanate interactions: A comparison of the effects of aryl vs alkyl isocyanates. Environ. Health Perspect. 72, 5-11.
    • (1987) Environ. Health Perspect. , vol.72 , pp. 5-11
    • Brown, W.E.1    Green, A.H.2    Cedel, T.E.3    Cairns, J.4
  • 2
    • 15744368477 scopus 로고
    • Injury to the respiratory tract by isocyanates used in making lacquers
    • Swensson, A., Holmquist, C. E., and Lundgren, K. D. (1955) Injury to the respiratory tract by isocyanates used in making lacquers. Br. J. Ind. Med. 12 (1), 50-53.
    • (1955) Br. J. Ind. Med. , vol.12 , Issue.1 , pp. 50-53
    • Swensson, A.1    Holmquist, C.E.2    Lundgren, K.D.3
  • 4
    • 0004131205 scopus 로고
    • Lea and Febiger, Philadelphia, PA
    • Fisher, A. A. (1967) Contact Dermatitis, pp 134-135, Lea and Febiger, Philadelphia, PA.
    • (1967) Contact Dermatitis , pp. 134-135
    • Fisher, A.A.1
  • 6
    • 0018120696 scopus 로고
    • Bathtub refinisher's lung: An unusual response to toluene diisocyanate
    • Fink, J. N., and Schlueter, D. P. (1978) Bathtub refinisher's lung: An unusual response to toluene diisocyanate. Am. Rev. Respir. Dis. 118 (5), 955-959.
    • (1978) Am. Rev. Respir. Dis. , vol.118 , Issue.5 , pp. 955-959
    • Fink, J.N.1    Schlueter, D.P.2
  • 7
    • 0024410909 scopus 로고
    • Isocyanate exposure and hypersensitivity pneumonitis - Report of a probable case and prevalence of specific immunoglobulin G antibodies among exposed individuals
    • Selden, A. I., Belin, L., and Wass, U. (1989) Isocyanate exposure and hypersensitivity pneumonitis - Report of a probable case and prevalence of specific immunoglobulin G antibodies among exposed individuals. Scand. J. Work Environ. Health 15 (3), 234-237.
    • (1989) Scand. J. Work Environ. Health , vol.15 , Issue.3 , pp. 234-237
    • Selden, A.I.1    Belin, L.2    Wass, U.3
  • 9
    • 0030722528 scopus 로고    scopus 로고
    • The prevention of occupational asthma in industries
    • Fabri, G. (1997) The prevention of occupational asthma in industries. J. Invest. Allerg. Clin. Immunol. 7 (5), 377-379.
    • (1997) J. Invest. Allerg. Clin. Immunol. , vol.7 , Issue.5 , pp. 377-379
    • Fabri, G.1
  • 10
    • 0030950388 scopus 로고    scopus 로고
    • A state-based surveillance system for work-related asthma
    • Rosenman, K. D., Reilly, M. J., and Kalinowski, D. J. (1997) A state-based surveillance system for work-related asthma. J. Occup. Environ. Med. 39 (5), 415-425.
    • (1997) J. Occup. Environ. Med. , vol.39 , Issue.5 , pp. 415-425
    • Rosenman, K.D.1    Reilly, M.J.2    Kalinowski, D.J.3
  • 12
    • 0028274207 scopus 로고
    • Predictive value of airways hyperresponsiveness and to circulating IgE for identifying types of responses to toluene diisocyanates inhalation challenge
    • Karol, M. H., Tollerud, D. J., Campbell, T. P., Fabbri, L., Mastrelli, P., Saetta, M., and Mapp, C. E. (1994) Predictive value of airways hyperresponsiveness and to circulating IgE for identifying types of responses to toluene diisocyanates inhalation challenge. Am. J. Respir. Crit. Care Med. 149 (3 Part 1), 611-615.
    • (1994) Am. J. Respir. Crit. Care Med. , vol.149 , Issue.3 PART 1 , pp. 611-615
    • Karol, M.H.1    Tollerud, D.J.2    Campbell, T.P.3    Fabbri, L.4    Mastrelli, P.5    Saetta, M.6    Mapp, C.E.7
  • 15
    • 4644282781 scopus 로고    scopus 로고
    • Increased levels of IgG to cytokeratin 19 in sera of patients with toluene diisocyanate-induced asthma
    • Choi, J. H., Nahm, D. H., Kim, S. H., Kim, Y. S., Suh, C. H., Park, H. S., and Ahn, S. W. (2004) Increased levels of IgG to cytokeratin 19 in sera of patients with toluene diisocyanate-induced asthma. Ann. Allergy, Asthma, Immunol. 93 (3), 293-298.
    • (2004) Ann. Allergy, Asthma, Immunol. , vol.93 , Issue.3 , pp. 293-298
    • Choi, J.H.1    Nahm, D.H.2    Kim, S.H.3    Kim, Y.S.4    Suh, C.H.5    Park, H.S.6    Ahn, S.W.7
  • 16
    • 0023697357 scopus 로고
    • Diisocyanate antigens that detect specific antibodies in exposed workers and guinea pigs
    • Jin, R. Z., and Karol, M. H. (1988) Diisocyanate antigens that detect specific antibodies in exposed workers and guinea pigs. Chem. Res. Toxicol. 1 (5), 288-293.
    • (1988) Chem. Res. Toxicol. , vol.1 , Issue.5 , pp. 288-293
    • Jin, R.Z.1    Karol, M.H.2
  • 17
    • 0033033442 scopus 로고    scopus 로고
    • Specific IgG response to monomeric and polymeric diphenylmethane diisocyanate conjugates in subjects with respiratory reactions to isocyanates
    • Aul, D. J., Bhaumik, A., Kennedy, A. L., Brown, W. E., Lesage, J., and Malo, J. L. (1999) Specific IgG response to monomeric and polymeric diphenylmethane diisocyanate conjugates in subjects with respiratory reactions to isocyanates. J. Allergy Clin. Immunol. 103 (5 Part 1), 749-755.
    • (1999) J. Allergy Clin. Immunol. , vol.103 , Issue.5 PART 1 , pp. 749-755
    • Aul, D.J.1    Bhaumik, A.2    Kennedy, A.L.3    Brown, W.E.4    Lesage, J.5    Malo, J.L.6
  • 18
    • 0032827632 scopus 로고    scopus 로고
    • Isocyanate-conjugated human lung epithelial cell proteins: A link between exposure and asthma?
    • Wisnewski, A. V., Lemus, R., Karol, M. H., and Redlich, C. A. (1999) Isocyanate-conjugated human lung epithelial cell proteins: A link between exposure and asthma? J. Allergy Clin. Immunol. 104 (2 Part 1), 341-347.
    • (1999) J. Allergy Clin. Immunol. , vol.104 , Issue.2 PART 1 , pp. 341-347
    • Wisnewski, A.V.1    Lemus, R.2    Karol, M.H.3    Redlich, C.A.4
  • 19
    • 0032724702 scopus 로고    scopus 로고
    • Intracellular S-glutathionyl adducts in murine lung and human bronchoepithelial cells after exposure to diisocyanatotoluene
    • Lange, R. W., Day, B. W., Lemus, R., Tyurin, V. A., Kagan, V. E., and Karol, M. H. (1999) Intracellular S-glutathionyl adducts in murine lung and human bronchoepithelial cells after exposure to diisocyanatotoluene. Chem. Res. Toxicol. 12 (10), 931-936.
    • (1999) Chem. Res. Toxicol. , vol.12 , Issue.10 , pp. 931-936
    • Lange, R.W.1    Day, B.W.2    Lemus, R.3    Tyurin, V.A.4    Kagan, V.E.5    Karol, M.H.6
  • 20
    • 0030909675 scopus 로고    scopus 로고
    • Formation, solvolysis, and transcarbamoylation reactions of bis(S-glutationyl) 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-glutationyl) 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
  • 21
    • 0036802394 scopus 로고    scopus 로고
    • Synthesis, characterization, and solvolysis of mono- and bis-S-(glutathionyl) adducts of methylene-bis-(phenylisocyanate) (MDI)
    • Reisser, M., Schmidt, B. F., and Brown, W. E. (2002) Synthesis, characterization, and solvolysis of mono- and bis-S-(glutathionyl) adducts of methylene-bis-(phenylisocyanate) (MDI). Chem. Res. Toxicol. 15 (10), 1235-1241.
    • (2002) Chem. Res. Toxicol. , vol.15 , Issue.10 , pp. 1235-1241
    • Reisser, M.1    Schmidt, B.F.2    Brown, W.E.3
  • 22
    • 0016636179 scopus 로고
    • An improved 2,4,6-trinitrobenzenesulfonic acid method for the determination of amines
    • Snyder, S. L., and Sobocinski, P. Z. (1975) An improved 2,4,6-trinitrobenzenesulfonic acid method for the determination of amines. Anal. Biochem. 64 (1), 284-288.
    • (1975) Anal. Biochem. , vol.64 , Issue.1 , pp. 284-288
    • Snyder, S.L.1    Sobocinski, P.Z.2
  • 23
    • 0344389015 scopus 로고    scopus 로고
    • 2,4-toluenediisocyanate and hexamethylene-diisocyanate adducts with blood proteins: Assessment of reactivity of amino acid residues in vitro
    • Mraz, J., and Bouskova, S. (1999) 2,4-toluenediisocyanate and hexamethylene-diisocyanate adducts with blood proteins: Assessment of reactivity of amino acid residues in vitro. Chem.-Biol. Interact. 117 (2), 173-186.
    • (1999) Chem.-Biol. Interact. , vol.117 , Issue.2 , pp. 173-186
    • Mraz, J.1    Bouskova, S.2
  • 24
    • 0018416496 scopus 로고
    • Ellman's reagent: 5,5′-Dithiobis(2-nitrobenzoic acid) - A reexamination
    • Riddles, P. W., Blakeley, R. L., and Zerner, B. (1979) Ellman's reagent: 5,5′-Dithiobis(2-nitrobenzoic acid) - A reexamination. Anal. Biochem. 94 (1), 75-81.
    • (1979) Anal. Biochem. , vol.94 , Issue.1 , pp. 75-81
    • Riddles, P.W.1    Blakeley, R.L.2    Zerner, B.3
  • 25
    • 0002681419 scopus 로고
    • The mechanism of the reaction of the aryl isocyanates with alcohols and amines
    • Baker, J. W., and Gaunt, J. (1949) The mechanism of the reaction of the aryl isocyanates with alcohols and amines. Part IV. J. Chem. Soc. 19, 24-27.
    • (1949) Part IV. J. Chem. Soc. , vol.19 , pp. 24-27
    • Baker, J.W.1    Gaunt, J.2
  • 27
    • 0001506594 scopus 로고
    • Glutathione: A vehicle for the transport of chemically reactive metabolites in vivo
    • Baillie, T. A., and Slatter, J. G. (1991) Glutathione: A vehicle for the transport of chemically reactive metabolites in vivo. Acc. Chem. Res. 24, 264-270.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 264-270
    • Baillie, T.A.1    Slatter, J.G.2
  • 28
    • 0025971563 scopus 로고
    • Bicarbonate-catalyzed hydrolysis of hexamethylene diisocyanate to 1,6-diaminohexane
    • Berode, M., Testa, B., and Savolainen, H. (1991) Bicarbonate-catalyzed hydrolysis of hexamethylene diisocyanate to 1,6-diaminohexane. Toxicol. Lett. 56 (1-2), 173-178.
    • (1991) Toxicol. Lett. , vol.56 , Issue.1-2 , pp. 173-178
    • Berode, M.1    Testa, B.2    Savolainen, H.3
  • 29
    • 84961978608 scopus 로고    scopus 로고
    • Experimental and theoretical evidence for a concerted catalysis by water clusters in the hydrolysis of isocyanates
    • Raspoet, G., Nguyen, M. T., McGarraghy, M., and Hegarty, A. F. (1998) Experimental and theoretical evidence for a concerted catalysis by water clusters in the hydrolysis of isocyanates. J. Org. Chem. 63 (20), 6867-6877.
    • (1998) J. Org. Chem. , vol.63 , Issue.20 , pp. 6867-6877
    • Raspoet, G.1    Nguyen, M.T.2    McGarraghy, M.3    Hegarty, A.F.4
  • 30
    • 0033030493 scopus 로고    scopus 로고
    • Kinetics of oxidation of aliphatic and aromatic thiols by myeloperoxidase compounds I and II
    • Burner, U., Jantschko, W., and Obinger, C. (1999) Kinetics of oxidation of aliphatic and aromatic thiols by myeloperoxidase compounds I and II. FEBS Lett. 443 (3), 290-296.
    • (1999) FEBS Lett. , vol.443 , Issue.3 , pp. 290-296
    • Burner, U.1    Jantschko, W.2    Obinger, C.3
  • 31
    • 0000708923 scopus 로고
    • Kinetic studies of the reaction of phenyl isocyanate with alcohols in various solvents
    • Ephraim, S., Woodward, A. E., and Mesrobian, R. B. (1958) Kinetic studies of the reaction of phenyl isocyanate with alcohols in various solvents. J. Am. Chem. Soc. 80, 1326-1328.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 1326-1328
    • Ephraim, S.1    Woodward, A.E.2    Mesrobian, R.B.3
  • 32
    • 0035909506 scopus 로고    scopus 로고
    • Differentiation of the mechanism of micronuclei induced by cysteine and glutathione conjugates of methylenedi-p-phenyl diisocyanate from that of 4,4′-methylenedianiline
    • Zhong, B. Z., Depree, G. J., and Siegel, P. D. (2001) Differentiation of the mechanism of micronuclei induced by cysteine and glutathione conjugates of methylenedi-p-phenyl diisocyanate from that of 4,4′-methylenedianiline. Mutat. Res. 497 (1-2), 29-37.
    • (2001) Mutat. Res. , vol.497 , Issue.1-2 , pp. 29-37
    • Zhong, B.Z.1    Depree, G.J.2    Siegel, P.D.3
  • 33
    • 33645466562 scopus 로고    scopus 로고
    • Phenyl isocyanate is a potent chemical sensitizer
    • Karol, M. H., and Baillie, T. A. (1996) Phenyl isocyanate is a potent chemical sensitizer. Toxicology 4 (2), 157-161.
    • (1996) Toxicology , vol.4 , Issue.2 , pp. 157-161
    • Karol, M.H.1    Baillie, T.A.2
  • 34
    • 77957175711 scopus 로고
    • Phenyl isocyanate-induced asthma in rats following a 2-week exposure period
    • Pauluhn, J., Rungeler, W., and Mohr, U. (1995) Phenyl isocyanate-induced asthma in rats following a 2-week exposure period. Fundam. Appl. Toxicol. 24 (2), 217-228.
    • (1995) Fundam. Appl. Toxicol. , vol.24 , Issue.2 , pp. 217-228
    • Pauluhn, J.1    Rungeler, W.2    Mohr, U.3
  • 35
    • 0035065855 scopus 로고    scopus 로고
    • Rapid reduction of intracellular glutathione in human bronchial epithelial cells exposed to occupational levels of toluene diisocyanate
    • Lantz, R. C., Lemus, R., Lange, R. W., and Karol, M. H. (2001) Rapid reduction of intracellular glutathione in human bronchial epithelial cells exposed to occupational levels of toluene diisocyanate. Toxicol. Sci. 60 (2), 348-355.
    • (2001) Toxicol. Sci. , vol.60 , Issue.2 , pp. 348-355
    • Lantz, R.C.1    Lemus, R.2    Lange, R.W.3    Karol, M.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.