Electrophilic reactions of skin-sensitizing sultones

Chemical Research in Toxicology

Volumn 20, Issue 1, 2007, Pages 61-71

  Roberts, David W ^a,c   Williams, Douglas L ^a,b   Bethell, Donald ^b  

^a UNILEVER RESEARCH   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; BUTYLAMINE; HEX 1 ENE 1,3 SULTONE; HEXADEC 1 ENE 1,3 SULTONE; HEXANE 1,3 SULTONE; PROTEIN; SERUM ALBUMIN; SODIUM HYDROXIDE; SODIUM METABISULFITE; SULTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HUMAN; MICHAEL ADDITION; PROTEIN TERTIARY STRUCTURE; SKIN SENSITIZATION; THERMODYNAMICS;

BUTYLAMINES; HUMANS; PROTEIN BINDING; SERUM ALBUMIN; SKIN; SODIUM HYDROXIDE; SULFONES;

EID: 33846851738     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx600330u     Document Type: Article

References (30)

1. Lepoittevin, J.-P., Basketter, D. A., Goosens, A., and Karlberg, A.-T., Eds. Allergic Contact Dermatitis. The Molecular Basis, Springer, Heidelberg.
2. Roberts, D. W., Aptula, O. A., and Patlewicz, G. Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published data set of 106 chemicals tested in the mouse local lymph node assay. Chem. Res. Toxicol. 2007, 20, 44-60.
3. Roberts, D. W., and Williams, D. L. (1982) The derivation of quantitative correlations between skin sensitisation and physicochemical parameters for alkylating agents and their application to experimental data for sultones. J. Theor. Biol. 99, 807-825.
4. Aptula, A. O., and Roberts, D. W. (2006) Mechanistic applicability domains for non-animal based toxicological endpoints. General principles, and application to reactive toxicity. Chem. Res. Toxicol. 19 (8), 1097-1105.
5. Roberts, D. W., Aptula, A. O., Cronin, M. T. D., Hulzebos, E., and Patlewicz, G. (2006) Global (Q)SARs for skin sensitization-Assessment against OECD principles. SAA QSAR, in press.
6. Aptula, A. O., Roberts, D. W., and Patlewicz, G. (2006) Mechanistic applicability domains for non-animal based toxicological endpoints. QSAR analysis of the Schiff Base applicability domain for skin sensitization. Chem. Res. Toxicol. 19 (9), 1228-1233.
7. Ritz, H. L., Connor, D. S., and Sauter, E. D. (1975) Contact sensitization of guinea pigs with unsaturated and halogenated sultones. Contact Dermatitis 1, 349-358.
8. Goodwin, B. F. J., Roberts, D. W., Williams, D. L., and Johnson, A. W. (1983) Skin sensitisation potential of saturated and unsaturated sultones. In Immunotoxicology (Gibson, G. G., Hubbard, R., and Parke, D. V., Eds.) pp 443-448, Academic Press, London.
9. Roberts, D. W., and Williams, D. L. (1983) Sultones as by-products in anionic surfactants. Tenside Deterg. 20, 109-111.
10. 13C-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones. Chem. Res. Toxicol. 14, 110-117.
11. 13C]-hexane-1,3-sultones to human serum albumin. Chem. Res. Toxicol. 14, 118-126.
12. Roberts, D. W., Sztanko, S., and Williams, D. L. (1981) An improved route to alk-1-ene 1,3 sultones, involving sulphonation of α-olefins by means of a sulphur trioxide/dioxan complex. Tenside Deterg. 18, 113-116.
13. Trowbridge, J. R., and Sundby, B. (1972) Canadian Patent CA 894,830.
14. Roberts, D. W. (1998) Sulfonation technology for anionic surfactant manufacture. Org. Proc. Res. Dev. 2, 194-202.
15. Roberts, D. W., and Williams, D. L. (1990) Formation of sultones in olefin sulphonation. J. Am. Oil Chem. Soc. 67, 1020-1027.
16. Roberts, D. W. (1997) Kinetics and mechanism in olefin sulphonation. Riv. Ital. Sostanze Grasse 74, 567-570.
17. Blaser, B. (1965) U.S. Patent 3,164,608.
18. Isaacs, N. (1995) Physical Organic Chemistry, 2nd ed., Longman, Harlow, United Kingdom.
19. Bordwell, F. G., Osborne, C. E., and Chapman, R. D. (1959) The hydrolysis of sultones. The effect of methyl groups on the rates of ring-opening solvolysis. J. Am. Chem. Soc. 81, 2698-2705.
20. Hine, J. (1962) Physical Organic Chemistry, 2nd ed., International Student Edition, McGraw-Hill, New York and Kogakusha, Tokyo.
21. Jones, J. B., and Young, J. M. (1966) Carcinogenicity of lactones. I. The reaction of 4-methylbuteno- and 4-methylbutano-γ-lactones with primary amines. Can. J. Chem. 44, 1059-1068.
22. Meyle, E., Keller, E., and Otto, H.-H. (1985) Darstellung und eigenschaften von 2,3-disubstituirten 1,2-thiazetidin-1,1-dioxiden. Liebigs Ann. Chem. 802-812.
23. Kirby, A. J. (1980) Effective molarities for intramolecular reactions. Adv. Phys. Org. Chem. 17, 183-278.
24. Tamai, I., Yokoi, K., and Ichikawa, C. (1971) German Patent GE 2,164,179.
25. 13C-Enriched methyl alkanesulfonates: New lipophilic methylating agents for the identification of nucleophilic amino acids of proteins by NMR. Tetrahedron Lett. 33, 3875-3878.
26. Smith, C. K., and Hotchkiss, S. A. M. (2001) Allergic Contact Dermatitis. Chemical and Metabolic Mechanisms, pp 210-214, Tayor and Francis, London, United Kingdom.
27. Barratt, M. D., Basketter, D. I., and Roberts, D. W. (1997) Structure-activity relationships for contact hypersensitivity. In Allergic Contact Dermatitis. The Molecular Basis (Lepoittevin, J.-P., Basketter, D. A., Goosens, A., and Karlberg, A.-T., Eds.) pp 129-154, Springer, Heidelberg.
28. Roberts, D. W., and Basketter, D. A. (1990) A quantitative structure-activity/dose relationship for contact allergenic potential of alkyl group transfer agents. Contact Dermatitis 23, 331-335.
29. Roberts, D. W., and Basketter, D. A. (1997) Further evaluation of the quantitative structure-activity relationship for skin-sensitizing alkyl transfer agents. Contact Dermatitis 37, 107-112.
30. Aptula, A. O., Patlewicz, G., and Roberts, D. W. (2005) Skin sensitization: Reaction mechanistic applicability domains for structure-activity relationships. Chem. Res. Toxicol. 18, 1420-1426.