Toluene diisocyanate reactivity with glutathione across a vapor/liquid interface and subsequent transcarbamoylation of human albumin

Chemical Research in Toxicology

Volumn 24, Issue 10, 2011, Pages 1686-1693

  Wisnewski, Adam V ^a   Hettick, Justin M ^b   Siegel, Paul D ^b  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NATIONAL INSTITUTE FOR OCCUPATIONAL SAFETY AND HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALBUMIN; GLUTATHIONE; LYSINE; TOLUENE DIISOCYANATE;

ALLERGENICITY; ARTICLE; BIOPHYSICS; CARBAMOYLATION; CHEMICAL REACTION; CONJUGATION; CONTROLLED STUDY; ELECTROPHORETIC MOBILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIQUID; LOWER RESPIRATORY TRACT; MASS SPECTROMETRY; NONHUMAN; PH; PRECIPITATION; PROTEIN CONFORMATION; TANDEM MASS SPECTROMETRY; VAPOR;

ALBUMINS; ALLERGENS; CARBAMATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUTATHIONE; HUMANS; TANDEM MASS SPECTROMETRY; TOLUENE 2,4-DIISOCYANATE; VOLATILIZATION;

EID: 80054731709     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2002433     Document Type: Article

References (40)

1. Baur, X., Marek, W., Ammon, J., Czuppon, A. B., Marczynski, B., Raulf-Heimsoth, M., Roemmelt, H., and Fruhmann, G. (1994) Respiratory and other hazards of isocyanates Int. Arch. Occup. Environ. Health 66, 141-152 (Pubitemid 24296527)
2. Collins, M. A. (2002) Toxicology of toluene diisocyanate Appl. Occup. Environ. Hyg. 17, 846-855 (Pubitemid 35424011)
3. Lindberg, H. K., Korpi, A., Santonen, T., Sakkinen, K., Jarvela, M., Tornaeus, J., Ahonen, N., Jarventaus, H., Pasanen, A. L., Rosenberg, C., and Norppa, H. (2011) Micronuclei, hemoglobin adducts and respiratory tract irritation in mice after inhalation of toluene diisocyanate (TDI) and 4,4′-methylenediphenyl diisocyanate (MDI) Mutat. Res. 723, 1-10
4. NIOSH (1996) Preventing Asthma and Death from Diisocyanate Exposure, DHHS (NIOSH) Publication Number 96-111, U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control, National Institute for Occupational Safety and Health, Cincinnati, OH.
5. NIOSH (1989) Current Intelligence Bulletin 53: Toluene Diisocyanate (TDI) and Toluenediamine (TDA), Evidence of Carcinogenicity, DHHS (NIOSH) Publication No. 90-101, U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control, National Institute for Occupational Safety and Health, Cincinnati, OH.
6. Duncan, B., Scheel, L. D., Fairchild, E. J., Killens, R., and Graham, S. (1962) Toluene Diisocyanate Inhalation Toxicity: Pathology and Mortality Am. Ind. Hyg. Assoc. J. 23, 447-456
7. Allport, D. C., Gilbert, D. S., and Outterside, S. M. (2003) MDI and TDI: Safety, Health and the Environment: A Source Book and Practical Guide, Wiley, Chichester, U.K.
8. Wisnewski, A. V. and Jones, M. (2010) Pro/Con debate: Is occupational asthma induced by isocyanates an immunoglobulin E-mediated disease? Clin. Exp. Allergy 40, 1155-1162
9. Ye, Y. M., Kim, C. W., Kim, H. R., Kim, H. M., Suh, C. H., Nahm, D. H., Park, H. S., Redlich, C. A., and Wisnewski, A. V. (2006) Biophysical determinants of toluene diisocyanate antigenicity associated with exposure and asthma J. Allergy Clin. Immunol. 118, 885-891 (Pubitemid 44498750)
10. 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 (Pubitemid 27176305)
11. 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, 931-936 (Pubitemid 29498366)
12. 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, 348-355 (Pubitemid 32273324)
13. Haenen, S., Vanoirbeek, J. A., De Vooght, V., Maes, E., Schoofs, L., Nemery, B., Hoet, P. H., and Clynen, E. (2010) Proteome analysis of multiple compartments in a mouse model of chemical-induced asthma J. Proteome Res. 9, 5868-5876
14. Kim, S. H., Choi, G. S., Ye, Y. M., Jou, I., Park, H. S., and Park, S. M. (2010) Toluene diisocyanate (TDI) regulates haem oxygenase-1/ferritin expression: implications for toluene diisocyanate-induced asthma Clin. Exp. Immunol. 160, 489-497
15. Broberg, K. E., Warholm, M., Tinnerberg, H., Axmon, A., Jonsson, B. A., Sennbro, C. J., Littorin, M., and Rannug, A. (2010) The GSTP1 Ile105 Val polymorphism modifies the metabolism of toluene di-isocyanate Pharmacogenet. Genomics 20, 104-111
16. Mapp, C. E., Fryer, A. A., De Marzo, N., Pozzato, V., Padoan, M., Boschetto, P., Strange, R. C., Hemmingsen, A., and Spiteri, M. A. (2002) Glutathione S-transferase GSTP1 is a susceptibility gene for occupational asthma induced by isocyanates J. Allergy Clin. Immunol. 109, 867-872 (Pubitemid 34499523)
17. Piirila, P., Wikman, H., Luukkonen, R., Kaaria, K., Rosenberg, C., Nordman, H., Norppa, H., Vainio, H., and Hirvonen, A. (2001) Glutathione S-transferase genotypes and allergic responses to diisocyanate exposure Pharmacogenetics 11, 437-445 (Pubitemid 32656584)
18. Reynaert, N. L. Glutathione biochemistry in asthma. Biochim. Biophys. Acta 2011, in press.
19. Boyd, M. R., Stiko, A., Statham, C. N., and Jones, R. B. (1982) Protective role of endogenous pulmonary glutathione and other sulfhydryl compounds against lung damage by alkylating agents. Investigations with 4-ipomeanol in the rat Biochem. Pharmacol. 31, 1579-1583 (Pubitemid 12161776)
20. Patterson, C. E. and Rhoades, R. A. (1988) Protective role of sulfhydryl reagents in oxidant lung injury Exp. Lung. Res. 14 (Suppl) 1005-1019 (Pubitemid 19016173)
21. Chipinda, I., Stetson, S. J., Depree, G. J., Simoyi, R. H., and Siegel, P. D. (2006) Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester Chem. Res. Toxicol. 19, 341-350
22. Karol, M. H., Macina, O. T., and Cunningham, A. (2001) Cell and molecular biology of chemical allergy Ann. Allergy Asthma Immunol. 87, 28-32 (Pubitemid 34001021)
23. Davis, M. R., Kassahun, K., Jochheim, C. M., Brandt, K. M., and Baillie, T. A. (1993) Glutathione and N-acetylcysteine conjugates of 2-chloroethyl isocyanate. Identification as metabolites of N,N′-bis(2-chloroethyl)-N- nitrosourea in the rat and inhibitory properties toward glutathione reductase in vitro Chem. Res. Toxicol. 6, 376-383 (Pubitemid 23146603)
24. 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
25. Pearson, P. G., Slatter, J. G., Rashed, M. S., Han, D. H., Grillo, M. P., and Baillie, T. A. (1990) S-(N-methylcarbamoyl)glutathione: a reactive S-linked metabolite of methyl isocyanate Biochem. Biophys. Res. Commun. 166, 245-250 (Pubitemid 20040178)
26. Fleischel, O., Gimenez-Arnau, E., and Lepoittevin, J. P. (2009) Nuclear magnetic resonance studies on covalent modification of amino acids thiol and amino residues by monofunctional aryl 13C-isocyanates, models of skin and respiratory sensitizers: transformation of thiocarbamates into urea adducts Chem. Res. Toxicol. 22, 1106-1115
27. 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
28. Ebino, K., Lemus, R., and Karol, M. H. (1999) The importance of the diluent for airway transport of toluene diisocyanate following intranasal dosing of mice Inhalation Toxicol. 11, 171-185 (Pubitemid 29167247)
29. Williams, K. R. and Stone, K. L. (1997) Enzymatic cleavage and HPLC peptide mapping of proteins Mol. Biotechnol. 8, 155-167 (Pubitemid 127498451)
30. Stone, K. L., Bjornson, R. D., Blasko, G. G., Bruce, C., Cofrancesco, R., Carriero, N. J., Colangelo, C. M., Crawford, J. K., Crawford, J. M., daSilva, N. C., Deluca, J. D., Elliott, J. I., Elliott, M. M., Flory, P. J., Folta-Stogniew, E. J., Gulcicek, E., Kong, Y., Lam, T. T., Lee, J. Y., Lin, A., LoPresti, M. B., Mane, S. M., McMurray, W. J., Tikhonova, I. R., Westman, S., Williams, N. A., Wu, T. L., Hongyu, Z., and Williams, K. R. (2007) Keck Foundation Biotechnology Resource Laboratory, Yale University Yale J. Biol. Med. 80, 195-211
31. Wisnewski, A. V., Liu, J., and Redlich, C. A. (2010) Antigenic changes in human albumin caused by reactivity with the occupational allergen diphenylmethane diisocyanate Anal. Biochem. 400, 251-258
32. Wisnewski, A. V., Stowe, M. H., Cartier, A., Liu, Q., Liu, J., Chen, L., and Redlich, C. A. (2004) Isocyanate vapor-induced antigenicity of human albumin J. Allergy Clin. Immunol. 113, 1178-1184 (Pubitemid 38858003)
33. Ruwona, T. B., Johnson, V. J., Schmechel, D., Simoyi, R. H., Beezhold, D., and Siegel, P. D. (2010) Monoclonal antibodies against toluene diisocyanate haptenated proteins from vapor-exposed mice Hybridoma (Larchmt) 29, 221-229
34. Chakraborty, A. B., Berger, S. J., and Gebler, J. C. (2007) Use of an integrated MS - multiplexed MS/MS data acquisition strategy for high-coverage peptide mapping studies Rapid Commun. Mass Spectrom. 21, 730-744 (Pubitemid 46340317)
35. Hettick, J. M. and Siegel, P. D. (2011) Determination of the toluene diisocyanate binding sites on human serum albumin by tandem mass spectrometry Anal. Biochem. 414, 232-238
36. Bodem, C. R., Lampton, L. M., Miller, D. P., Tarka, E. F., and Everett, E. D. (1983) Endobronchial pH. Relevance of aminoglycoside activity in gram-negative bacillary pneumonia Am. Rev. Respir. Dis. 127, 39-41 (Pubitemid 13168307)
37. Brown, W. E. and Burkert, A. L. (2002) Biomarkers of toluene diisocyanate exposure Appl. Occup. Environ. Hyg. 17, 840-845 (Pubitemid 35424010)
38. Wass, U. and Belin, L. (1989) Immunologic specificity of isocyanate-induced IgE antibodies in serum from 10 sensitized workers J. Allergy Clin. Immunol. 83, 126-135 (Pubitemid 19052824)
39. Wisnewski, A. V., Liu, Q., Liu, J., and Redlich, C. A. (2005) Glutathione protects human airway proteins and epithelial cells from isocyanates Clin. Exp. Allergy 35, 352-357 (Pubitemid 40516663)
40. 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, 1235-1241