Characterization of sulfur mustard induced structural modifications in human hemoglobin by liquid chromatography-tandem mass spectrometry

Chemical Research in Toxicology

Volumn 9, Issue 4, 1996, Pages 781-787

  Noort, Daan ^a   Verheij, Elwin R ^a   Hulst, Albert G ^a   De Jong, Leo P A ^a   Benschop, Hendrik P ^a  

^a TNO   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

GLOBIN; HEMOGLOBIN; MUSTARD GAS; TRYPSIN;

ALKYLATION; ARTICLE; BLOOD; CHEMICAL WARFARE; HUMAN; LIQUID CHROMATOGRAPHY; PROTEIN MODIFICATION; TANDEM MASS SPECTROMETRY;

ALKYLATION; AMINO ACID SEQUENCE; CARCINOGENS; CHEMICAL WARFARE AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERYTHROCYTES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEMOGLOBINS; HUMANS; MOLECULAR SEQUENCE DATA; MUSTARD GAS; PEPTIDE FRAGMENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFUR RADIOISOTOPES; TRYPSIN;

EID: 0029894028     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9502148     Document Type: Article

References (30)

1. (a) Report of the specialists appointed by the Secretary-General to investigate allegations by the Islamic Republic of Iran concerning the use of chemical weapons. UN document S/16, 433, 26 March, 1984.
2. (b) Van Biema, D. (1995) Prophet of poison. Time Magazine 145, (13), 14-21.
3. Papirmeister, B., Feister, A. J., Robinson, S. I., and Ford, R. D. (1991) Medical Defense against Mustard Gas. Toxic Mechanisms and Pharmacological Implications, CRC Press, Boca Raton, FL.
4. Black, R. M., Brewster, K., Clarke, R. J., Hambrook, J. L., Harrison, J. M., and Howells, D. J. (1992) Biological fate of sulphur mustard, 1,1′-thiobis(2-chloroethane): isolation and identification of urinary metabolites following intraperitoneal administration to rat. Xenobiotica 22, 405-418.
5. Fidder, A., Moes, G. W. H., Scheffer, A. G., Van der Schans, G. P., Baan, R. A., De Jong, L. P. A., and Benschop, H. P. (1994) Synthesis, characterization, and quantitation of the major adducts formed between sulfur mustard and DNA of calf thymus and human blood. Chem. Res. Toxicol. 7, 199-204.
6. Van der Schans, G. P., Scheffer, A. G., Mars-Groenendijk, R. H., Fidder, A., Bensehop, H. P., and Baan, R. A. (1994) Immunochemical detection of adducts of sulfur mustard to DNA of calf thymus and human white blood cells. Chem. Res. Toxicol. 7, 408-413.
7. Blair, I. A. (1993) Applications of mass spectrometry to toxicology. Chem. Res. Toxicol. 6, 741-747.
8. Törnqvist, M. (1994) Epoxide adducts to N-terminal valine of hemoglobin. Methods Enzymol. 231 B, 650-657.
9. Fidder, A., Noort, D., De Jong, A. L., Trap, H. C., De Jong, L. P. A., and Benschop, H. P. (1996) Monitoring of in vitro and in vivo exposure to sulfur mustard by GC/MS determination of the N-terminal valine adduct in hemoglobin after a modified Edman degradation. Chem. Res. Toxicol. 9, 788-792.
10. Skipper, P. L., Peng, X., SooHoo, C. K., and Tannenbaum, S. R. (1994) Protein adducts as biomarkers of human carcinogen exposure. Drug Metab. Rev. 26, 111-124.
11. Kaur, S., Hollander, D., Haas, R., and Burlingame (1989) Characterization of structural xenobiotic modifications in proteins by high sensitivity tandem mass spectrometry. J. Biol. Chem. 264, 16981-16984.
12. Ding, A., Zia-Amirhosseini, P., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1995) Reactivity of tolmetin glucuronide with human serum albumin. Drug Metab. Dispos. 23, 369-376.
13. Ding, A., Ojingwa, J. C., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1993) Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc. Natl. Acad. Sci. U.S.A. 90, 3797-3801.
14. Erve, J. C. L., Deinzer, M. L., and Reed, D. J. (1995) Alkylation of oxytocin by S-(2-chloroethyl)glutathione and characterization of adducts by tandem mass spectrometry and Edman degradation. Chem. Res. Toxicol. 8, 414-421.
15. Erve, J. C. L., Barofsky, E., Barofsky, D. F., Deinzer, M. L., and Reed, D. J. (1995) Alkylation of Escherichia coli thioredoxin by S-(2-chloroethyl)glutathione and identification of the adduct on the active site cysteine-32 by mass spectrometry. Chem. Res. Toxicol. 8, 934-941.
16. Yu, X., Wu, Z., and Fenselau, C. (1995) Covalent sequestration of melphalan by metallothionein and selective alkylation of cysteines. Biochemistry 34, 3377-3385.
17. 35. Chem. Ber. 91, 681-682.
18. Boursnell, J. C., Francis, G. E., and Wormall, A. (1946) Studies on mustard gas and some related compounds. III. The preparation and use of mustard gas containing a) radioactive sulfur and b) deuterium. Biochem. J. 40, 743-745.
19. Bailey, E., Brooks, A. G. F., Dollery, C. T., Farmer, P. B., Passingham, B. J., Sleightholm, M. A., and Yates, D. W. (1988) Hydroxyethylvaline adduct formation in haemoglobin as a biological monitor of cigarette smoke intake. Arch. Toxicol. 62, 247-253.
20. Bruenner, B. A., Jones, A. D., and German, J. B. (1994) Maximum entropy deconvolution of heterogeneity in protein modification: protein adducts of 4-hydroxy-2-nonenal. Rapid Commun. Mass Spectrom. 8, 509-512.
21. Bergmark, E., Belew, M., and Osterman-Golkar, S. (1990) Separation and enrichment of alkylated globin chains as a means of improving the sensitivity of hemoglobin adduct measurement. Acta Chem. Scand. 44, 630-635.
22. Roepstorff, P., and Fohlmann, J. (1984) Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Environ. Mass Spectrom. 11, 601-603.
23. Fenn, J. B., Mann, M., Meng, C. K., Wong, S. F., and Whitehouse, C. M. (1989) Electrospray ionization for mass spectrometry of large biomolecules. Science 246, 64-71.
24. Springer, D. L., Bull, R. J., Goheen, S. C., Sylvester, D. M., and Edmonds, C. G. (1993) Electrospray ionization mass spectrometric characterization of acrylamide adducts to hemoglobin. J. Toxicol. Environ. Health 40, 161-176.
25. Bruenner, B. A., Jones, A. D., and German, J. B. (1995) Direct characterization of protein adducts of the lipid peroxidation product 4-hydroxy-2-nonenal using electrospray mass spectrometry. Chem. Res. Toxicol. 8, 552-559.
26. Sannolo, N., Carbone, V., Ferranti, P., Fiume, I., Mamone, G., and Malorni, A. (1995) Mass spectrometric analysis of haemoglobin adducts formed by methyl bromide in vitro. J. Chromatogr. B 670, 349-353.
27. Chervet, J. P., Van Soest, R. E. J., and Salzmann, J. P. (1992) Recent advances in capillary liquid chromatography. Enhanced detectability in bioanalysis. LC·GC 5 (7), 33-38.
28. Black, R. M., Brewster, K., Clarke, R. J., and Harrison, J. M. (1992) The chemistry of 1,1′-thiobis(2-chloroethane) (sulphur mustard). Part II. The synthesis of some conjugates with cysteine, N-acetylcysteine and N-acetylcysteine methyl ester. Phosporus, Sulfur, Silicon Relat. Elem. 71, 49-58.
29. Evelo, C. T. A., Kon, T. C., Fijneman, P. H. S., and Henderson, P. Th. (1988) Separation of human haemoglobin alkylated at β93 cysteine from its native form by fast protein liquid chromatography. J. Chromatogr. 427, 335-340.
30. Noort, D., Jacobs, E. H., Fidder, A., De Jong, L. P. A., Drijfhout, J. W., and Benschop, H. P. (1995) Solid-phase synthesis of peptide haptens containing a cysteine-sulfur mustard adduct. Int. J. Peptide Protein Res. 45, 497-500.