Reactions of 4 methylphenyl isocyanate with amino acids

References

• BELAND, F. A. AND KADLUBAR, F. F. (1990) Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Chemical Carcinogenesis and Mutagenesis I, C. S. Cooper and P. L. Grover, eds (Springer Verlag, Heidelberg) pp. 267–325.
   Google Scholar
• BIRNER, G., AND NEUMANN, H.-G. (1988) Biomonitoring of aromatic amines. II: Hemoglobin binding of some monocyclic aromatic amines. Archives of Toxicology, 62, 110–115.
   Google Scholar
• BROWN, W. E. (1975) Alkyl isocyanates as active and specific reagents for serine proteases. Location of alkyl binding site in chymotrypsin by X-ray diffraction. Biochemistry, 14, 5079–5084.
   PubMedGoogle Scholar
• BROWN, W. E. (1986) The chemistry and biochemistry of isocyanates: an overview. In Current Topics in Pulmonary Pharmacology and Toxicology, M. A. Hollinger, ed. (Elsevier Science Publishing Co., New York), pp. 200-225.
   Google Scholar
• BROWN, J. R. AND SHOCKLEY, P. (1982) Serum albumin: structure and characterization of ts ligand binding sites. In Lipid—Protein Interactions, P. C. Jost and 0. H. Griffith, eds (John Wiley and Sons, New York), Vol. 1, pp. 25–68.
   Google Scholar
• BROWN, W. E. AND WOLD, F. (1973) Alkyl isocyanates as active site specific reagents for serine proteases. Identification of the active-site serine as the site of reaction. Biochemistry, 12, 835–851.
   PubMed Web of Science ®Google Scholar
• BROWN, W. E., GREEN, A. H., KAROL, M. H. AND ALARIE, Y. C. E. (1982) Inhibition of cholinesterase activity by isocyanates. Toxicology and Applied Pharmacology, 63, 45–52.
   PubMedGoogle Scholar
• 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. Environmental Health Perspectives, 72, 5–11.
   PubMed Web of Science ®Google Scholar
• EDMAN, P. (1949) A method for the determination of the amino acid sequence in peptides. Archives of Biochemistry and Biophysics, 22, 475–490. EDMAN, P. AND HENSCHEN, A.(1975) Sequence determination. In Protein Sequence Determination, S. B. Needleman, ed. (Springer-Verlag, Berlin), pp. 232–279.
   Google Scholar
• EYER, P. (1988) Detoxication of N-oxygenated arylamines in erythrocytes. An overview. Xenobiotica, 18, 1327–1333.
   PubMed Web of Science ®Google Scholar
• GAME, C. J. A. (1982) Australian TDI workers' sera assayed for IgE against a p-tolyl-isocyanate —human serum albumin conjugate. American Industrial Hygiene Association Journal, 43, 759–763.
   PubMed Web of Science ®Google Scholar
• GUAN, X., DAVIS, M. R., JIN, L. AND BAILLIE, T. A. (1994) Identification of S-(n-butylcarbamoyl)glutathione, a reactive carbamoylating agent, as a biliary metabolite of benomyl in the rat. Journal of Agricultural and Food Chemistry, 42, 2953–2957.
   Web of Science ®Google Scholar
• GUNTHER, H. (1995) NMR Spectroscopy (John Wiley & Sons, Chichester). HESSE, M., MEIER, H. AND ZEEH, B. (1984) Spektroskopische Methoden in der organischen Chemie (Georg Thieme Verlag, Stuttgart).
   Google Scholar
• HUBBELL, J. P. AND CASIDA, J. E. (1977) Metabolic fate of the N,N-diakylcarbamoyl moiety of thiocarbamate herbicides in rats and corn. Journal of Agricultural and Food Chemistry, 25, 404–413.
   PubMed Web of Science ®Google Scholar
• JOCHHEIM, C. M. AND BAILLIE, T. A. (1994) Selective and irreversible inhibition of glutathione reductase in Wtro by carbamate thioester conjugates of methyl isocyanate. Biochemical Pharmacology, 47, 1197–1206.
   PubMed Web of Science ®Google Scholar
• KADLUBAR, F. F. AND BELAND, F. A. (1985) Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. In Polycyclic Hydrocarbons and Carcinogenesis (ACS Symposium Series No. 283), R. G. Harve, ed. (American Chemical Society, Washington), pp. 341–370. KADLUBAR, F. F., TALASKA, G., LANG, N. P., BENSON, R. W. AND ROBERTS, D. W. (1989) Assessment of exposure and susceptibility to aromatic amine carcinogens. In Methods for Detecting DNA Damaging Agents in Humans: Applications in Cancer Epidemiology and Prevention (IARC Scientific Publications No. 89), H. Bartsch, K. Hemminki and I. K. O'Neill, eds (International Agency for Research on Cancer, Lyon), pp. 166–180. KALINOWSKI, H. 0., BERGER, S. AND BRAUN, S. (1984) '3C-NMR-Spektroskopie (Georg Thieme Verlag, Stuttgart, New York).
   Google Scholar
• KAROL, M. H., losEr, H. H., RILEY, E. J. AND ALARIE, Y. C. (1978a) Hapten-specific respiratory hypersensitivity in guinea pigs. American Industrial Hygiene Association Journal, 39, 546–556.
   PubMed Web of Science ®Google Scholar
• KAROL, M. H., HOLLY, H., losEr, H. H., RILEY, E. J. AND ALARIE, Y. C. (1978b)Toly1 specific IgE antibodies in workers with hypersensitivity to toluene diisocyanate. American Industrial Hygiene Association Journal, 39, 454–458.
   PubMed Web of Science ®Google Scholar
• KAZANIS, S. AND MCCLELLAND, R. A. (1992) Electrophilic intermediate in the reaction of glutathione and nitrosoarenes. Journal of the American Chemical Society, 114, 3052–3059.
   Google Scholar
• 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. Biochemical Biophysical Research Communications, 166, 245–250.
   PubMed Web of Science ®Google Scholar
• PEARSON, P. G., SLATTER, J. G., RASHED, M. S., HAN, D. H. AND BAILLIE, T. A. (1991) Carbamoylation of peptides and proteins in Wtro by S-(N-methylcarbamoyl) glutathione and S-(N-methylcarbamoyl) cysteine, two electrophilic S-linked conjugates of methyl isocyanate. Chemical Research in Toxicology, 4, 436–444.
   PubMed Web of Science ®Google Scholar
• RISCH, A., SMELT, V., LANE, D., STANLEY, L., VAN DER SLOT, W., WARD, A. AND SIM, E. (1996) Arylamine N-acetyttransferase in erythrocytes of cystic fibrosis patients. Pharmacology and Toxicology, 78, 235–240.
   PubMedGoogle Scholar
• SABBIONI, G. (1990) Chemical and physical properties of the major serum albumin adduct of aflatoxin 131 and their implications for the quantification in biological samples. Chemico-Biological Interactions, 75, 1–15.
   PubMed Web of Science ®Google Scholar
• SABBIONI, G. (1992) Quanttative structure activity relationship of the N-oxidation of aromatic amines. Chemico-Biological Interactions, 81, 91–117.
   PubMed Web of Science ®Google Scholar
• SABBIONI, G. (1994a) Hemoglobin binding of arylamines and nitroarenes: molecular dosimetry and quanttative structure activity relationships. Environmental Health Perspectives, 102 (Su ppl 6), 61–67.
   Google Scholar
• SABBIONI, G. (1994b) Hemoglobin binding of nbtrarenes and quantitative structure—activity relationships. Chemical Research in Toxicology, 7, 267–274.
   PubMed Web of Science ®Google Scholar
• SABBIONI, G. AND BEYERBACH, A. (1995) Determination of hemoglobin adducts of arylamines in humans. Journal of Chromatography B, 667, 75–83.
   PubMedGoogle Scholar
• SABBIONI, G. AND SEPAI, 0. (1995) Comparison of hemoglobin binding, mutagenicity and carcinogeniay of arylamines and ntroarenes. Chimia, 49, 374–380.
   Google Scholar
• SCHÜTZE, D., SEPAI, 0., LEWALTER, J., MIKSCHE, L., HENSCHLER, D. AND SABBIONI, G. (1995) Biomonitoring of workers exposed to 4,4"-methylenedianiline or 4,4"-methylenediphenyl diisocyanate. Carcinogenesis, 16, 573–582.
   Google Scholar
• SEPAI, 0., HENSCHLER, D. AND SABBIONI, G. (1995a) Albumin adducts, hemoglobin adducts and urinary metabolites in workers exposed to 4,4"-methylenediphenyl diisocyanate. Carcinogenesis, 16, 2583–2587.
   Google Scholar
• SEPAI, 0., HENSCHLER, D., CZECH, S., ECKERT, P. AND SABBIONI, G. (1995b) Exposure to toluene diamines from polyurethane-coated breast implants. Toxicology Letters, 77, 371–378.
   Google Scholar
• SEPAI, 0., SCHÜTZE, D., HEINRICH, U., HOYMANN, H. G., HENSCHLER, D. AND SABBIONI, G. (1995c) Hemoglobin adducts and urine metabolites of 4,4% methylenedianiline after 4,4"-methylenediphenyl diisocyanate exposure to rats. Chemico-Biological. Interactions, 97, 185–198.
   Google Scholar
• SKARPING, G. AND DALENE, M. (1995) Determination of 4,4"-methylenedianiline (MDA) and identification of isomers in technical grade MDA in hydrolyzed plasma and urine from workers exposed to methylenediphenyl diisocyanate by gas chromatography—mass spectrometry. Journal of Chromatography B, 663, 209–216.
   PubMedGoogle Scholar
• SKARPING, G., DALENE, M., SVENSSON, B.-G., LITTORIN, M., AKESSON, B., WELINDER, H. AND SKERFVING, S. (1996) Biomarkers of exposure, antibodies, and respiratory symptoms in workers heating polyurethane glue. Occupational and Environmental Medicine, 53, 180–187.
   Google Scholar
• SKIPPER, P. (1996) Influence of tertiary structure on nucleophilic subsiftution reactions of proteins. Chemical Research in Toxicology, 9, 918-923. 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. Chemical Research in Toxicology, 4, 157–161.
   Google Scholar
• SLATTER, J. G., DAVIS, M. R., HAN, D. H., PEARSON, P. G. AND BAILLIE, T. A. (1993) Studies on the metabolic fate of caracemide, an experimental antitumor agent, in the rat. Evidence for the release of methyl isocyanate in vivo. Chemical Research in Toxicology, 6, 335–340.
   PubMedGoogle Scholar
• STARK, G. R. AND SMITH, D. G. (1963) The use of cyanate for the determination of NH2-terminal residues in proteins. Journal of Biological Chemistry, 238, 214–221.
   PubMedGoogle Scholar
• TORNQVIST, M., MOWRER, S. J., JENSEN, S. AND EHRENBERG, L. (1986) Monitoring of environmental cancer initiators through hemoglobin adducts by a modified Edman degradation method. Analytical Biochemistry, 154, 255-266. TUMA, D. J. AND SORRELL, M. F. (1985) Covalent binding of acetaldehyde in hepatic proteins: role in alcoholic liver injury. In Aldehyde Adducts in Alcoholism, M. A. Collins, ed. (Alan R. Liss Inc., New York), pp. 3-19. Twu, J.-S. AND WOLD, F. (1973) Butyl isocyanate, an active site specific reagent for yeast alcohol dehydrogenase. Biochemistry, 12, 381-386. VASAN, S., ZHANG, X., ZHANG, X., KAPURNIOTU, A., BERNHAGEN, J., TEICHBERG, S., BASGEN, J., WAGLE, D., SHIH, D., TERLECKY, I., BUCALA, R., CERAMI, A., EN, J. AND ULRICH, P. (1996) An agent cleaving glucose-derived protein crosslinks in vitro and in vivo. Nature, 382, 275–278.
   Google Scholar
• VOELTER, W., JUNG, G., BREITMAIER, E. AND BAYER, E. (1971) DC-NMR Verschiebungen von Aminosauren und Peptiden. Zeitung für Naturforschung Sektion B, 26, 213–222.
   PubMedGoogle Scholar
• WOTHRICH, K. (1987) NMR in Biological Research: Peptides and Proteins (Elsevier/North Holland, New York), pp. 43–50.
   Google Scholar