Effect of glutathione on the covalent binding of the 13C-labeled skin sensitizer 5-chloro-2-methylisothiazol-3-one to human serum albumin: Identification of adducts by nuclear magnetic resonance, matrix-assisted laser desorption/ionization mass spectrometry, and nanoelectrospray tandem mass spectrometry

Chemical Research in Toxicology

Volumn 17, Issue 9, 2004, Pages 1280-1288

  Alvarez Sánchez, Rubén ^a   Divkovic, Maja ^b   Basketter, David ^c   Pease, Camilla ^c   Panico, Maria ^b   Dell, Anne ^b   Morris, Howard ^b   Lepoittevin, Jean Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNILEVER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 CHLORO 2 METHYL 4 ISOTHIAZOLIN 3 ONE; AMIDE; CARBON 13; CYSTEINE; GLUTATHIONE; HISTIDINE; HUMAN SERUM ALBUMIN; ISOTHIAZOLE DERIVATIVE; LYSINE; PEPTIDE DERIVATIVE; SKIN SENSITIZER; THIOAMIDE; TYROSINE; UNCLASSIFIED DRUG;

ADDITION REACTION; AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; COVALENT BOND; ELIMINATION REACTION; HUMAN; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TANDEM MASS SPECTROMETRY; TECHNIQUE;

BINDING SITES; CARBON ISOTOPES; CHEMISTRY, ANALYTICAL; DNA ADDUCTS; GLUTATHIONE; HISTIDINE; HUMANS; LYSINE; MAGNETIC RESONANCE SPECTROSCOPY; SERUM ALBUMIN; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; THIAZOLES;

EID: 4644257235     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049935+     Document Type: Article

References (11)

1. Roberts, D. W., and Lepoittevin, J.-P. (1997) Hapten protein interactions. In Allergic Contact Dermatitis: The Molecular Basis (Lepoittevin, J. P., Basketter, D. A., Goossens, A., and Karlberg, A. T., Eds.) pp 81-111, Springer, Berlin, Heidelberg, New York.
2. Rustmeyer, T., von Hoogstraten, M. W., von Blumberg, M. E., and Scheper, R. J. (2001) Mechanisms in allergic contact dermatitis. In Textbook of Contact Dermatitis (Rycroft, R. J. G., Menné, T., Frosch, P. J., and Lepoittevin, J. P., Eds.) pp 13-58, Springer, Berlin, Heidelberg, New York.
3. Lepoittevin, J.-P., and Leblond, I. (1997) Hapten-protein-T cell receptor interactions. Eur. J. Dermatol. 7, 151-154.
4. Barratt, M. D., Basketter, D. A., and Roberts, D. W. (1997) Hapten protein interactions. In Allergic Contact Dermatitis: The Moleclular Basis (Lepoittevin, J. P., Basketter, D. A., Goossens, A., and Karlberg, A. T., Eds.) pp 129-154, Springer, Berlin, Heidelberg, New York.
5. 13C]hexane-1,3-sultones to human serum albumin. Chem. Res. Toxicol. 14, 118-126.
6. + T cells. Immunobiology 189, 57.
7. Henriot, S., Lepoittevin, J. P., and Trifilieff, E. (2001) Haptenization of ovalbumin with the skin sensitizer methyloctane-sulfonate: Characterization of the methylated OVA323-339 T-cell epitope at His331. J. Pept. Sci. 7, 331-337.
8. Collier, P. J., Ramsey, A., Waigh, R. D., Douglas, K. T., Austin, P., and Gilbert, P. (1990) Chemical reactivity of some isothiazolone biocides. J. Appl. Bacteriol. 69, 578-584.
9. 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methyl-isothiazol-3-one (MI). Chem. Res. Toxicol. 16, 627-636.
10. Alvarez-Sanchez, R., Basketter, D. A., Pease, C., and Lepoittevin, J.-P. (2004) Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2- methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione. Bioorg. Med. Chem. Lett. 14, 365-368.
11. Michell, S. L., Whelan, A. O., Wheeler, P. R., Panico, M., Easton, R. L., Etienne, A. T., Haslam, S. M., Dell, A., Morris, H. R., Reason, A. J., Herrman, J. L., Young, D. B., Hewinson, R. G. (2003) The MPB83 antigen from Mycobacterium bovis contains O-linked mannose and (1-3)-mannobiose moieties. J. Biol. Chem. 278, 16423-16432.