Vapor conjugation of toluene diisocyanate to specific lysines of human albumin

Analytical Biochemistry

Volumn 421, Issue 2, 2012, Pages 706-711

  Hettick, Justin M ^a   Siegel, Paul D ^a   Green, Brett J ^a   Liu, Jian ^b   Wisnewski, Adam V ^b  

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

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Allergy; Human serum albumin; Tandem mass spectrometry; Toluene diisocyanate

Indexed keywords

ALLERGIES; AMINO ACIDS; MASS SPECTROMETRY;

BIOLOGICAL RESPONSE; CROSS LINKING AGENTS; DOSE-DEPENDENT MANNER; EXPOSURE BIOMARKERS; HUMAN SERUM ALBUMINS; POLYURETHANE PRODUCTS; TANDEM MASS SPECTROMETRY; TOLUENE DIISOCYANATES;

TOLUENE;

BIOLOGICAL MARKER; HUMAN ALBUMIN; LYSINE; LYSINE DERIVATIVE; POLYURETHAN; TOLUENE DIISOCYANATE;

ARTICLE; CONJUGATION; EXPOSURE; OCCUPATIONAL ASTHMA; PRIORITY JOURNAL; PROTEIN DOMAIN; QUANTITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; VAPOR;

EID: 84859732066     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2011.12.013     Document Type: Article

References (30)

1. D.C. Allport, D.S. Gilbert, S.M. Outterside, MDI, TDI, and the polyurethane industry, in: D.C. Allport, D.S. Gilbert, S.M. Outterside (Eds.), MDI and TDI: Safety, Health, and the Environment, John Wiley, Chichester, UK, 2003, pp. 11-23.
2. National Institute for Occupational Safety and Health, A Summary of Health Hazard Evaluations: Issues Related to Occupational Exposure to Isocyanates, 1989-2002, Department of Health and Human Services, Centers for Disease Control and Prevention, National Institute for Occupational Safety and Health, Cincinnati, OH, 2004.
3. C.V. Porter, R.L. Higgins, L.D. Scheel, A retrospective study of clinical, physiologic, and immunologic changes in workers exposed to toluene diisocyanate, Am. Ind. Hyg. Assoc. J. 36 (1975) 159-168.
4. W.G. Adams, Long-term effects on the health of men engaged in the manufacture of tolylene di-isocyanate, Br. J. Ind. Med. 32 (1975) 72-78.
5. W.G. White, M.J. Morris, E. Sugden, E. Zapata, Isocyanate-induced asthma in a car factory, Lancet 1 (1980) 756-760.
6. R. Jin, B.W. Day, M.H. Karol, Toluene diisocyanate protein adducts in the bronchoalveolar lavage of guinea pigs exposed to vapors of the chemical, Chem. Res. Toxicol. 6 (1993) 906-912. (Pubitemid 23351217)
7. 14C during and following inhalation exposure to radioactive toluene diisocyanate, Toxicol. Appl. Pharmacol. 100 (1989) 280-292.
8. A.V. Wisnewski, R. Srivastava, C. Herick, L. Xu, R. Lemus, H. Cain, N.M. Magoski, M.H. Karol, K. Bottomly, C.A. Redlich, Identification of human lung and skin proteins conjugated with hexamethylene diisocyanate in vitro and in vivo, Am. J. Respir. Crit. Care Med. 162 (2000) 2330-2336. (Pubitemid 32051708)
9. P. Lind, M. Dalene, V. Lindstrom, A. Grubb, G. Skarping, Albumin adducts in plasma from workers exposed to toluene diisocyanate, Analyst 122 (1997) 151-154. (Pubitemid 27100144)
10. A. Cartier, L. Grammer, J.L. Malo, F. Lagier, H. Ghezzo, K. Harris, R. Patterson, Specific serum antibodies against isocyanates: association with occupational asthma, J. Allergy Clin. Immunol. 84 (1989) 507-514. (Pubitemid 19266747)
11. R.D. Tee, P. Cullinan, J. Welch, P.S. Burge, A.J. Newman-Taylor, Specific IgE to isocyanates: a useful diagnostic role in occupational asthma, J. Allergy Clin. Immunol. 101 (1998) 709-715. (Pubitemid 28228317)
12. U. Wass, L. Belin, Immunologic specificity of isocyanate-induced IgE antibodies in serum from 10 sensitized workers, J. Allergy Clin. Immunol. 83 (1989) 126-135. (Pubitemid 19052824)
13. P. Campo, A.V. Wisnewski, Z. Lummus, A. Cartier, J.L. Malo, L.P. Boulet, D.I. Bernstein, Diisocyanate conjugate and immunoassay characteristics influence detection of specific antibodies in HDI-exposed workers, Clin. Exp. Allergy 37 (2007) 1095-1102. (Pubitemid 46955522)
14. J.M. Hettick, P.D. Siegel, Determination of the toluene diisocyanate binding sites on human serum albumin by tandem mass spectrometry, Anal. Biochem. 414 (2011) 232-238.
15. C.S. Tse, A.J. Pesce, Chemical characterization of isocyanate-protein conjugates, Toxicol. Appl. Pharmacol. 51 (1979) 39-46. (Pubitemid 10198914)
16. Y.M. Ye, C.W. Kim, H.R. Kim, H.M. Kim, C.H. Suh, D.H. Nahm, H.S. Park, C.A. Redlich, A.V. Wisnewski, Biophysical determinants of toluene diisocyanate antigenicity associated with exposure and asthma, J. Allergy Clin. Immunol. 118 (2006) 885-891. (Pubitemid 44498750)
17. A.V. Wisnewski, M.H. Stowe, A. Cartier, Q. Liu, J. Liu, L. Chen, C.A. Redlich, Isocyanate vapor-induced antigenicity of human albumin, J. Allergy Clin. Immunol. 113 (2004) 1178-11784.
18. X. Baur, Z. Chen, A. Flagge, A. Posch, M. Raulf-Heimsoth, EAST and CAP specificity for the evaluation of IgE and IgG antibodies to diisocyanate-HSA conjugates, Int. Arch. Allergy Immunol. 110 (1996) 332-338. (Pubitemid 26237988)
19. A.V. Wisnewski, J.M. Hettick, P.D. Siegel, Toluene diisocyanate reactivity with glutathione across a vapor/liquid interface and subsequent transcarbamoylation of human albumin, Chem. Res. Toxicol. 24 (2011) 1686-1693.
20. J.M. Hettick, T.B. Ruwona, P.D. Siegel, Structural elucidation of isocyanate-peptide adducts using tandem mass spectrometry, J. Am. Soc. Mass Spectrom. 20 (2009) 1567-1575.
21. J.W. Morgan, J.M. Hettick, D.H. Russell, Peptide sequencing by MALDI 193-nm photodissociation TOF MS, Methods Enzymol. 402 (2005) 186-209. (Pubitemid 43053128)
22. A.B. Chakraborty, S.J. Berger, J.C. Gebler, Use of an integrated MS-multiplexed MS/MS data acquisition strategy for high-coverage peptide mapping studies, Rapid Commun. Mass Spectrom. 21 (2007) 730-744. (Pubitemid 46340317)
23. J.M. Hettick, P.D. Siegel, Comparative analysis of aromatic diisocyanate conjugation to human albumin utilizing multiplexed tandem mass spectrometry, Int. J. Mass Spectrom., 2011, doi:10.1016/j.ijms.2011.09.015.
24. A.V. Wisnewski, J. Liu, C.A. Redlich, Antigenic changes in human albumin caused by reactivity with the occupational allergen diphenylmethane diisocyanate, Anal. Biochem. 400 (2010) 251-258.
25. T.B. Ruwona, V.J. Johnson, J.M. Hettick, D. Schmechel, D. Beezhold, W. Wang, R.H. Simoyi, P.D. Siegel, Production, characterization, and utility of a panel of monoclonal antibodies for the detection of toluene diisocyanate haptenated proteins, J. Immunol. Methods 373 (2011) 127-135.
26. P. Roepstorff, J. Fohlman, Proposal for a common nomenclature for sequence ions in mass spectra of peptides, Biomed. Mass Spectrom. 11 (1984) 601.
27. J.M. Lin, J.C. Ang, J.W. White, Resistance of b-casein at the air-water interface to enzymatic cleavage, Langmuir 26 (2010) 18985-18991.
28. E.V. Kudryashova, M.B. Meinders, A.J. Visser, A. van Hoek, H.H. de Jongh, Structure and dynamics of egg white ovalbumin adsorbed at the air/water interface, Eur Biophys J 32 (2003) 553-562. (Pubitemid 37408659)
29. M. Dockal, D.C. Carter, F. Ruker, The three recombinant domains of human serum albumin: structural characterization and ligand binding properties, J. Biol. Chem. 274 (1999) 29303-29310.
30. X.M. He, D.C. Carter, Atomic structure and chemistry of human serum albumin, Nature 358 (1992) 209-215.