Determinants of skin sensitisation potential

Journal of Applied Toxicology

Volumn 28, Issue 3, 2008, Pages 377-387

  Roberts, David W ^a   Aptula, Aynur O ^b  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

Antigen recognition; Migration; Penetration; Protein binding; Skin sensitiser

Indexed keywords

CARRIER PROTEIN;

ANTIGEN PRESENTATION; ANTIGEN RECOGNITION; ARTICLE; CELL MATURATION; CELL MIGRATION; CHEMISTRY; COVALENT BOND; HYDROPHOBICITY; LANGERHANS CELL; PREDICTION; PRIORITY JOURNAL; PROTEIN DOMAIN; QUANTITATIVE ANALYSIS; SKIN PENETRATION; SKIN SENSITIZATION; STRATUM CORNEUM; STRUCTURE ANALYSIS; T LYMPHOCYTE;

ADMINISTRATION, TOPICAL; ALLERGENS; ANIMAL TESTING ALTERNATIVES; ANTIGEN PRESENTATION; CELL MOVEMENT; COMPUTATIONAL BIOLOGY; DERMATITIS, CONTACT; LANGERHANS CELLS; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SKIN; T-LYMPHOCYTES; XENOBIOTICS;

ANIMALIA;

EID: 42049110135     PISSN: 0260437X     EISSN: 10991263     Source Type: Journal    
DOI: 10.1002/jat.1289     Document Type: Article

References (57)

1. Aptula AO, Patlewicz GY, Roberts DW. 2005. Skin sensitisation: Reaction mechanistic applicability domains for structure-activity relationships. Chem. Res. Toxicol. 18: 1420-1426.
2. Aptula AO, Roberts DW. 2006. Mechanistic applicability domains for non-animal based toxicological endpoints. General principles, and application to reactive toxicity. Chem. Res. Toxicol. 19: 1097-1105.
3. Aptula AO, Roberts DW, 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: 1228-1233.
4. Ashby J, Basketter DA, Paton D, Kimber I. 1995. Structure activity relationships in skin sensitization using the murine local lymph node assay. Toxicology 103: 177-194.
5. Barratt MD, Basketter DA, Roberts DW. 1997. Structure-activity relationships for contact hypersensitivity. In Allergic Contact Dermatitis. The Molecular Basis, Lepoittevin J-P, Basketter DA, Goossens A, Karlberg A-T (eds). Springer: Heidelberg; 129-154.
6. Basketter DA. 1998. Chemistry of contact allergens and irritants. Am. J. Contact. Derm. 9: 119-124.
7. Basketter DA, Evans P, Fielder RJ, Gerberick GF, Dearman RJ, Kimber I. 2002. Local lymph node assay - validation, conduct and use in practice. Food Chem. Toxicol. 40: 593-598.
8. Basketter DA, Gerberick GF, Kimber I. 2001. Skin sensitization, vehicle effects and the local lymph node assay. Food Chem. Toxicol. 39: 621-627.
9. Basketter DA, Roberts DW. 1990. Structure/activity relationships in contact allergy. Int. J. Cosmet. Sci. 12: 81-90.
10. Basketter DA, Roberts DW, Cronin M, Scholes EW. 1992. The value of the local lymph node assay in quantitative structure-activity investigations. Contact Dermatitis 27: 137-142.
11. Corsini E, Galli CL. 2000. Epidermal cytokines in experimental contact dermatitis. Toxicology 142: 203-211.
12. Cumberbatch M, Clelland K, Dearman RJ, Kimber I. 2005. Impact of cutaneous IL-10 on resident epidermal Langerhans' cells and the development of polarized immune responses. J. Immunol. 33: 47-62.
13. Cumberbatch M, Dearman RJ, Antonopoulos C, Groves RW, Kimber I. 2001. Interleukin (IL)-18 induces Langerhans cell migration by a tumour necrosis factor-alpha- and IL-1beta-dependent mechanism. Immunology 102: 323-330.
14. Cumberbatch M, Dearman RJ, Kimber I. 1997. Langerhans cells require signals from both tumour necrosis factor-alpha and interleukin-1 beta for migration. Immunology 92: 388-395.
15. Cumberbatch M, Scott RC, Basketter DA, Scholes EW, Hilton J, Dearman RJ, Kimber I. 1993. Influence of sodium lauryl sulphate on 2,4-dinitrochlorobenzene- induced lymph node activation. Toxicology 77: 181-191.
16. Dupuis G, Benezra C. 1982. Allergic Contact Dermatitis to Simple Chemicals: A Molecular Approach. Dekker: New York.
17. EU 2003. Directive 2003/15/EC of the European Parliament and the Council of 27 February 2003 amending Council Directive 76/768/EEC on the approximations of laws of the Member States relating to cosmetic products. Official J. Eur. Union L66: 26-35.
18. EU 2006. Council of the European Union. 2006. Common position adopted by the Council with a view to the adoption of a Regulation of the European Parliament and of the Council concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC of the European Parliament and of the Council and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. European Council document 7524/06 of 12 June 2006. http://europa.eu.int/comm/enterprise/ reach/index_en.htm
19. Enk AH, Katz SI. 1992. Early molecular events in the induction phase of contact sensitivity. Proc. Natl Acad. Sci. USA 89: 1398-1402.
20. Fedorowicz A, Singh H, Soderheim S, Demchuk E. 2005. Structure-activity models for contact sensitization. Chem. Res. Toxicol. 18: 954-969.
21. Franot C, Roberts DW, Basketter DA, Benezra C, Lepoittevin J-P. 1994. Structure-activity relationships for contact allergenic potential of γ,γ-dimethyl-γ-butyrolactone derivatives. 2. Quantitative structure-skin sensitisation relationships for α-substituted-α- methyl-γ,γ-dimethyl-γ-butyrolactones. Chem. Res. Toxicol. 7: 307-312.
22. Frost AA, Pearson RG. 1961. Kinetics and Mechanism, 2nd edn. Wiley: New York.
23. Gerberick GF, Ryan CA, Kern PS, Schlatter H, Dearman RJ, Kimber I, Patlewicz GY, Basketter DA. 2005. Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis 16: 157-202.
24. Jowsey IR, Basketter DA, Westmoreland C, Kimber I. 2006. A future approach to measuring relative skin sensitising potency: a proposal. J. Appl. Toxicol. 26: 341-350.
25. Kimber I, Cumberbatch M. 1992. Dendritic cells and cutaneous immune responses to chemical allergens. Toxicol. Appl. Pharmacol. 117: 137-146.
26. Kimber I, Cumberbatch M, Dearman RJ, Bhushan M, Griffiths CEM. 2000. Cytokines and chemokines in the initiation and regulation of epidermal Langerhans cell mobilization. Br. J. Dermatol. 142: 401-412.
27. Kimber I, Dearman R. 2003. What makes a chemical an allergen? Ann. Allergy Asthma Immunol. 90(Suppl): 28-31.
28. Kimber I, Dearman RJ, Basketter DA, Ryan CA, Gerberick GF. 2002. The local lymph node assay: past, present and future. Contact Dermatitis 47: 315-328.
29. Kimber I, Dearman RJ, Cumberbatch M, Huby RJ. 1998. Langerhans cells and chemical allergy. Curr. Opin. Immunol. 10: 614-619.
30. Kimber I, Pichowski JS, Betts CJ, Cumberbatch M, Basketter DA, Dearman RJ. 2001. Alternative approaches to the identification and characterization of chemical allergens. Toxicol. In Vitro 15: 307-312.
31. Kligman AM. 1983. Skin permeability: dermatological aspects of transdermal; delivery. Am. Heart J. 108: 200-206.
32. Landsteiner K, Jacobs J. 1936. Studies on the sensitization of animals with simple chemical compounds. J. Exp. Med. 64: 643-655.
33. Lepoittevin J-P, Basketter DA, Goossens A, Karlberg A-T (eds). 1997. Allergic Contact Dermatitis. The Molecular Basis. Springer: Heidelberg.
34. McMurry JE, Begley TP. 2005. The Organic Chemistry of Biological Pathways. Roberts: Englewood, Colorado, USA.
35. Maurer T, Arthur A, Bentley P. 1994. Guinea-pig contact sensitization assays. Toxicology 93: 47-54.
36. NAr electrophiles. Chem. Res. Toxicol. 10: 994-1000.
37. Menon GK, Grayson S, Elias PM. 1986. Cytochemical and biochemical localization of lipase and sphingomyelinase activity in mammalian epidermis. J. Invest. Derm. 86: 591-597.
38. Miller MD, Yourtee DM, Glaros AG, Chappelow CC, Eick JD, Holder AJ. 2005. Quantum mechanical structure-activity relationship analyses for skin sensitization. J. Chem. Inf. Model. 45: 924-929.
39. Playfair J. 2004. Living with Germs. In Sickness and in Health. Oxford University Press: Oxford, UK; 97-98.
40. Potts RO, Guy RH. 1992. Predicting skin permeability. Pharm. Res. 9: 663-669.
41. Ritz HL, Connor DS, Sauter ED. 1975. Contact sensitization of guinea pigs with unsaturated and halogenated sultones. Contact Dermatitis 1: 349-358.
42. Roberts DW. 1987. Structure-activity relationships for skin sensitisation potential of diacrylates and dimethacrylates. Contact Dermatitis 17: 281-289.
43. NAr electrophiles. Chem. Res. Toxicol. 8: 545-551.
44. Roberts DW, Aptula AO, Patlewicz G. 2007a. 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. 20: 44-60.
45. Roberts DW, Basketter DA. 1990. A quantitative structure-activity/dose relationship for contact allergenic potential of alkyl group transfer agents. Contact Dermatitis 23: 331-5.
46. Roberts DW, Basketter DA. 1997. Further evaluation of the quantitative structure-activity relationship for skin-sensitizing alkyl transfer agents. Contact Dermatitis 37: 107-112.
47. Roberts DW, Basketter DA. 2000. Quantitative structure-activity relationships: sulfonate esters in the local lymph node assay. Contact Dermatitis 42: 154-161.
48. Roberts DW, Goodwin BF, Basketter D. 1988. Methyl groups as antigenic determinants in skin sensitisation. Contact Dermatitis 18: 219-225.
49. Roberts DW, Goodwin BFJ, Williams DL, Jones K, Johnson AW, Alderson CJE. 1983. Correlations between skin sensitisation potential and chemical reactivity for p-nitrobenzyl compounds. Food Chem. Toxicol. 21: 811-813.
50. Roberts DW, Patlewicz G, Kern PS, Gerberick GF, Kimber I, Dearman RJ, Ryan CA, Basketter DA, Aptula AO. 2007b. Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitization. Chem. Res. Toxicol. 20: 1019-1030.
51. Roberts DW, Williams DL. 1982. The derivation of quantitative correlations between skin sensitisation and physico-chemical parameters for alkylating agents and their application to experimental data for sultones. J. Theor. Biol. 99: 807-825.
52. Roberts DW, Williams DL, Bethell D. 2007c. Electrophilic reactions of skin sensitizing sultones. Chem. Res. Toxicol. 20: 61-71.
53. Rustemeyer T, van Hoogstraten IMW, von Blomberg BME, Scheper R. 2006. Mechanisms in allergic contact dermatitis. In Contact Dermatitis, 4th edn, Frosch PJ, Menné T, Lepoittevin J-P (eds). Springer: Heidelberg; 11-44.
54. Ryan CA, Gerberick GF, Gildea LA, Hulette BC, Betts CJ, Cumberbatch M, Dearman RJ, Kimber I. 2005. Interactions of contact allergens with dendritic cells: opportunities and challenges for the development of novel approaches to hazard assessment. Toxicol. Sci. 88: 4-11.
55. De Silva O, Basketter DA, Barratt MD, Corsini E, Cronin MTD, Das PK, Degwert J, Enk A, Garrigue JL, Hauser C, Kimber I, Lepoittevin J-P, Peguet J, Ponec M. 1996. Alternative methods for skin sensitisation testing. The report and recommendations of ECVAM Workshop 19. ATLA 24: 683-705.
56. Smith CK, Hotchkiss SAM. 2001. Allergic Contact Dermatitis: Chemical and Metabolic Mechanisms. Taylor and Francis: London.
57. Wright ZM, Basketter DA, Blaikie L, Cooper KJ, Warbrick EV, Dearman RJ, Kimber I. 2001. Vehicle effects on skin sensitizing potency of four chemicals: assessment using the local lymph node assay. Int. J. Cosmet. Sci. 23: 75-83.