Biological fate of sulphur mustard : in vitro alkylation of human haemoglobin by sulphur mustard

References

• BAILEY, E., BROOKS, A. G. F., DOLLERY, C. T., FARMER, P. B., PASS1NGHAN, B. J., SLEIGHTHOLM, M. A. and YATES, D. W., 1988, Hydroxyethylvaline adduct formation in haemoglobin as a biological monitor of cigarette smoke intake. Archives of Toxicology, 61, 247–253.
   Google Scholar
• BLACK, R. M., BREWSTER, K., CLARKE, R. J., HAMBROOK, J. L., HARRISON, J. M. and HOWELLS, D. J., 1992a, Biological fate of sulphur mustard, 1 '1'- thiobis(2- chloroethane): isolation and identi-fication of urinary metabolites following intraperitoneal administration to rat. Xenobiotica, 22, 405–418.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M., CLARKE, R. J. and READ, R. W., 1991, A method for the analysis of 1,1 'sulphonylbis[(2 - methylsulphinyl )ethane] and 1,1'- sulphonylbi s[2- (methylsulphiny 1)-2 '-(methylthio)eth an e], metabolites of sulphur mustard, in urine using gas chromatography-mass spectrometry. Journal of Chromatography, 558, 405–414.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M., CLARKE, R. J., RFAo, R. W. and Rum, M. T. J., (1994), Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to the analysis of chemical warfare samples found to contain residues of the nerve agent sarin, sulphur mustard and their degradation products. Journal of Chromatography A, 662 301–321.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M., HAMBROOK, J. L., HOWELLS, D. J. and READ, R. W., 1992b, Biological fate of sulphur mustard, 1,1 '- thiobis(2-chloroethane): urinary excretion profiles of hydrolysis products and beta-lyase metabolites of sulphur mustard after cutaneous application in rats. Journal of Analytical Toxicology, 16, 79–84.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M. and READ, R. W., 1988, Detection of trace levels of thiodiglycol in blood, plasma and urine using gas chromatography-electron capture negative ion chemical ionisation mass spectrometry. Journal of Chromatography, 449, 261–270.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M. and READ, R. W., 1991, Methods for the analysis of thiodiglycol sulphoxide, a metabolite of sulphur mustard, in urine using gas chromatography-mass spectrometry. Journal of Chromato-graphy, 558, 393–404.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M. and READ, R. W., 1995a, Biological fate of sulphur mustard, 1,1'-thiobis(2-chloroethane): identification of /3-lyase metabolites and hydrolysis products in human urine. Xenobiotica, 25, 167–173.
   PubMed Web of Science ®Google Scholar
• BLACK, R. M. and READ, R. W., 1995b, Improved methodology for the detection and quantitation of urinary metabolites of sulphur mustard using gas chromatography-tandem mass spectrometry. Journal of Chromatography B, 665, 97–105.
   PubMed Web of Science ®Google Scholar
• CHAVES Dm NEVES, H. J. and VASCONCELOS, A. M. P., 1987, Capillary gas chromatography of amino acids, including asparagine and glutamine : sensitive gas chromatographic-mass spectrometric and selected ion monitoring gas chromatographic-mass spectrometric detection of the N, O(S)-tert-butyldimethylsi lyl derivatives. Journal of Chromatography, 392, 249–258.
   PubMed Web of Science ®Google Scholar
• EHRENBERG, L. and OSTERMAN -GOLKAR, S., 1980, Alkylation of macromolecules for detecting mutagenic agents. Teratogenesi.s Carcinogenesis and Mutagenesis 1, 105–127.
   Google Scholar
• FARMER, P. B., BAILEY, B., LAMB, J. H. and COORS, T. A., 1980. Approach to the quantitation of alkylatedamino acids in haemoglobin by gas chromatography mass spectrometry. Biomedical Mass Spectrometry, 7, 41–46.
   PubMedGoogle Scholar
• FARMER, P. B., BAILEY, B., NAYLOR, S., ANDERSON, D., BROOKS, A., CUSHN1R, J., LAMB, J. H., SEPAI, O. and TANG, Y., 1993, Identification of endogenous electrophiles by means of mass spectrometric determination of protein and DNA adducts. Environmental Health Perspectives, 99, 19–24.
   Google Scholar
• FIDDER, A., MOES, G. W. H., SCHEFTER, A. G., NAN 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. Chemistry Research in Toxicology, 7, 199–204.
   Google Scholar
• GRANT, W. M. and KINSEY, V. E., 1946, Synthetic preparation of 2- chloro-2'- hydroxydiethyl sulphide, reaction with cysteine and valine, and measurement of reaction rate in aqueous media. Journal of the American Chemical Society, 68, 2075–2076.
   PubMed Web of Science ®Google Scholar
• HAMBROOK, J. L., HARRISON, J. M., HOWELLS, D. J. and ScHocx, C., 1992, Biological fate of sulphur mustard (1,1'-thiobis(2-chloroethane): urinary and faecal excretion of S by rat after injection or cutaneous application of S- labelled sulphur mustard. Xenobiotica, 22, 65–75.
   PubMed Web of Science ®Google Scholar
• HAMBROOK, J. L., HOWELLS, D. J. and ScHocx, C., 1993, Biological fate of sulphur mustard, 1,1'-thiobis(2- chloroethane): uptake, distribution and retention of S in skin and in blood after cutaneous application of S- sulphur mustard in rat and comparison with human blood in vitro. Xenobiotica, 23, 537–561.
   PubMed Web of Science ®Google Scholar
• HARRISON, J. M., 1991, The synthesis of isotopically labelled 1,1 '- thiobis(2- chloroethane) and some related compounds. Journal of Labelled Compounds and Radiopharrnaceuticals,XXIX, 1175–1180.
   Web of Science ®Google Scholar
• LAWLEY, P. D. and BROOKES, P., 1967, Interstrand cross-linking of DNA by difunctional alkylating agents. Journal of Molecular Biology, 25, 143–160.
   PubMed Web of Science ®Google Scholar
• KAUR, S., HOLLANDER, D., HAAS, R. and BURLANGAME, A., 1989, Characterization of structural xenobiotic modifications in proteins by high sensitivity tandem mass spectrometry. Journal of Biological Chemistry, 264, 16981–16984.
   PubMed Web of Science ®Google Scholar
• MAISONNEUVE, A., CALLEBAT, I., DEBORDES, L. and COPPET, L., 1993, Biological fate of sulphur mustard in rat: toxicokinetics and disposition. Xenobiotica, 23, 771–780.
   PubMed Web of Science ®Google Scholar
• MOWRER, J., TORNQVIST, M., JENSEN, S. and EHRENBERG, L., 1986, Modified Edman degradation applied to hemoglobin for monitoring occupational exposure to alkylating agents. Toxicology and Environmental Chemistry, 11, 215–231.
   Web of Science ®Google Scholar
• NEUMANN, H.-G., 1984, Analysis of haemoglobin as a dose monitor for alkylating and arylating agents. Archives of Toxicology, 56, 1–6.
   PubMed Web of Science ®Google Scholar
• NEIS, J. M., VAN GEMERT, P. J. L., ROELOFS, H. M. J. M. and HENDERSON, P. T H., 1984, Disappearance of free SH- groups in hemoglobin of man, rat and rabbit after exposure to alkylating agents in vitro. Toxicology, 31, 319–327.
   Google Scholar
• NOORT, D., JACOBS, E. H., FIDDER, A., DE JONG, L. P. A., DRUFHOUT, J. W. and BENSCHOP, H. P., 1995, Solid phase synthesis of peptide haptens containing a cysteine- sulphur mustard adduct. International Journal of Peptide and Protein Research 45, 497–500.
   PubMedGoogle Scholar
• NOORT, D., VERHELT, E. R., HULST, A. G., DE JONG, L. P. A. and BENSCHOP, H. P., 1996, Charac-terization of sulphur mustard induced structural modifications of human hemoglobin by liquid chromatography-tandem mass spectrometry. Chemical Research in Toxicology, 9, 781–787.
   Google Scholar
• OSTERMAN -GOLKAR, S., MACNEELA, J. P., TURNER, M. J., WALKER, V. E., SWENBERG, J. A., SUMNER, S. J., YoursEv, N. and FENNELL, T. R., 1994, Monitoring exposure to acrylonitrile using adducts with N- terminal valine in hemoglobin. Carcinogenesis 15, 2701–2707.
   PubMed Web of Science ®Google Scholar
• PAPAYANNOPOULOS, I. A., 1995, The interpretation of collision-induced dissociation tandem mass spectra of peptides. Mass Spectrometry Reviews, 14, 49–73.
   Web of Science ®Google Scholar
• ROEPSTORFF, P. and FOHLMAN, J., 1984, Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomedical and Environmental Mass Spectrometry, 11, 601–604.
   Google Scholar
• TANG, X-J., T H1BAULT, P. and Bow, R. K., 1993, Fragmentation reactions of multiply- protonated peptides and implications for sequencing by tandem mass spectrometry with low-energy collision-induced dissociation. Analytical Chemistry, 65, 2824–2834.
   Google Scholar
• T ANNENBAUM, S. R. and SKIPPER, P. L., 1994, Quantitative analysis of haemoglobin-xenobiotic adducts. Methods in Enzymology, 231, 625–632.
   PubMed Web of Science ®Google Scholar
• UNITED NATIONS SECURITY COUNCIL, 1984, Report of the Specialists Appointed by the Secretary-General to Investigate Allegations by the Islamic Republic of Iran Concerning the Use of Chemical Weapons. S-16433 (New York: UN Security Council).
   Google Scholar
• UNITED NATIONS SECURITY COUNCIL, 1986, Report of the Mission Despatchedby the Secretary-General to Investigate Allegations of the Use of Chemical Weapons in the Conflict Between the Islamic Republics of Iran and Iraq. S-17911 (New York: UN Security Council).
   Google Scholar
• UNITED NATIONS SECURITY COUNCIL, 1988, Report of the Mission Despatchedby the Secretary-General to Investigate Allegations of the Use of Chemical Weapons in the Conflict Between the Islamic Republics of Iran and Iraq. S-20134 (New York: UN Security Council).
   Google Scholar
• WADA, Y., MATSUO, T. and SAKURAI, T., 1989, Structure elucidation of hemoglobin variants and other proteins by digit-printing method. Mass Spectrometry Reviews, 8, 379–434.
   Web of Science ®Google Scholar
• WOGAN, G. N., 1989, Markers of exposure to carcinogens. Environmental Health Perspectives, 81, 9–17.
   PubMed Web of Science ®Google Scholar