Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the 13c-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones

Chemical Research in Toxicology

Volumn 14, Issue 1, 2001, Pages 110-117

  Meschkat, Emmanuel ^a   Barratt, Martin D ^b,c   Lepoittevin, Jean Pierre ^a  

^a UNIVERSITY HOSPITAL OF STRASBOURG   (France)

^b UNILEVER RESEARCH   (United Kingdom)

^c Marlin Consultancy   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEX 1 ENE 1,3 SULTONE; 3 HEX 1 ENE 1,3 SULTONE; 3 HEXANE 1,3 SULTONE; BUTYLAMINE; CARBON 13; DIETHYLAMINE; HAPTEN; IMIDAZOLE; PHENOL; SULTONE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SKIN SENSITIZATION; SYNTHESIS;

BUTYLAMINES; CARBON ISOTOPES; HAPTENS; IMIDAZOLES; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENESULFONATES; PHENOL; SKIN; SULFHYDRYL COMPOUNDS;

EID: 0035148018     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000225n     Document Type: Article

References (6)

1. Rycroft, R. J. G., Menné, T., and Frosch, P. J., Eds. (1995) Textbook of contact dermatitis, Springer-Verlag, Berlin.
2. Lepoittevin, J. P., Basketter, D. A., Goossens, A., and Karlberg, A. T., Eds. (1997) Allergic contact dermatitis: the molecular basis, Springer, Berlin.
3. Lepoittevin, J. P., and Leblond, I. (1997) Hapten-peptide-T cell receptor interactions: molecular basis for the recognition of haptens by T lymphocytes. Eur. J. Dermatol. 7, 151-154.
4. Roberts, D. W., and Williams, D. L. (1982) The derivation of quantitative correlations between skin sensitization and physicochemical parameters for alkylating agents, and their application to experimental data for sultones. J. Theor. Biol. 99, 807-825.
5. Barratt, M., Basketter, D. A., and Roberts, D. W. (1997) Structure-activity relationships for contact hypersensitivity. In Allergic contact dermatitis, the molecular basis (Lepoittevin, J. P., et al., Eds.) pp 129-154, Springer, Berlin.
6. 13C-enriched methyl alkanesulfonates: new lipophilic methylating agents for the identification of nucleophilic amino acids of proteins by NMR. Tetrahedron Lett. 33, 3875-3878.