Molecular aspects in allergic and irritant contact dermatitis

Contact Dermatitis (Fifth Edition)

Volumn , Issue , 2011, Pages 91-110

  Lepoittevin, Jean Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84055169340     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-03827-3_4     Document Type: Chapter

References (54)

1. Baer H, Watkins RC, Kurtz AP, Byck JS, Dawson CR (1967) Delayed contact sensitivity to catechols. J Immunol 99: 307-375.
2. Corbett MD, Billets S (1975) Characterization of poison oak urushiol. J Pharm Sci 64:1715.
3. Landsteiner K, Jacobs J (1936) Studies on the sensitization of animals with simple chemical compounds. J Exp Med 64:625-639.
4. Lepoittevin JP, Berl V (1997) Chemical basis. In: Lepoittevin JP, Basketter DA, Goossens A, Karlberg AT (eds) Allergic contact dermatitis: The molecular basis. Springer, Berlin, pp 19-42.
5. Lepoittevin J-P, Benezra C (1992) 13C-Enriched methylalkanesulfonates: new lipophilic methylating agents for the identification of nucleophilic amino acids of protein by NMR. Tetrahedron Lett 33:3875-3878.
6. Franot C, Benezra C, Lepoittevin J-P (1993) Synthesis and interaction studies of 13C labeled lactone derivatives with a model protein using 13C NMR. Biorg Med Chem 1: 389-397.
7. Ritz HL, Connor DS, Sauter ED (1975) Contact sensitization of guinea-pigs with unsaturated and halogenated sultones. Contact Derm 1:349-358.
8. Goodwin BFJ, Roberts DW, Williams DL, Johnson AW (1983) Relationships between skin sensitization potential of saturated and unsaturated sultones. In: Gibson GG, Hubbard R, Parke DV (eds) Immunotoxicology. Academic Press, London, pp 443-448.
9. Magnusson B, Gilje O (1973) Allergic contact dermatitis from dishwashing liquid containing lauryl ether sulfate. Acta Derm Venereol (Stockholm) 53:136-140.
10. Meschkat E, Barratt M, Lepoittevin JP (2001) Studies of chemical selectivity of hapten, reactivity and skin sensitization potency. Synthesis and studies on the reactivity towards model nucleophiles of the 13C-labeled skin sensitizers, hex- 1-ene- And hexane-1, 3 sultones. Chem Res Toxicol 14: 110-117.
11. Meschkat E, Barratt M, Lepoittevin JP (2001) Studies of chemical selectivity of hapten, reactivity and skin sensitization potency. NMR studies of the covalent binding of the 13C-labeled skin sensitizers, 2-[13C] and 3-[13C]-hex-1-eneand 3-[13C]-hexane-1, 3-sultones to human serum albumin. Chem Res Toxicol 14:118-126.
12. Alvarez-Sanchez R, Basketter D, Pease C, Lepoittevin JP (2003) Studies of chemical selectivity of hapten, reactivity and skin sensitization potency. 3. Synthesis and studies on the reactivity towards model nucleophiles of the 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI). Chem Res Toxicol 16:627-636.
13. Alvarez-Sanchez R, Basketter DA, Pease C, Lepoittevin JP (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 Letters 14:365-368.
14. Alvarez-Sanchez R, Divkovic M, Basketter D, Pease C, Panico M, Dell A, Morris H, Lepoittevin JP (2004) Effect of glutathione on the covalent binding of the 13C-labeled skin sensitizer 5-chloro-2-methylisothiazol-3-one (MCI) to human serum albumin: identification of adducts by NMR, MALDI-MS and nano-ES MS/MS. Chem Res Toxicol 17(9):1280-1288.
15. Romagnoli P, Labahrdt AM, Sinigaglia F (1991) Selective interaction of nickel with an MHC bound peptide. EMBO J 10:1303-1306.
16. Schmidt R, Kahn L, Chung LY (1990) Are free radicals and quinones the haptenic species derived from urushiols and other contact allergenic mono- And dihydric alkylbenzenes? The significance of NADH, glutathione and redox cuycling in the skin. Arch Dermatol Res 282:56-64.
17. Barratt MD, Basketter DA (1992) Possible origin of the skin sensitization potential of eugenol and related compounds. Contact Derm 27:98-104.
18. Gäfvert E, Shao LP, Karlberg A-T, Nilsson U, Nilsson JLG (1994) Contact allergy to resin acid hydroperoxides. Hapten binding via free readicals and epoxides. Chem Res Toxicol 7:260-266.
19. Mutterer V, Gimenez-Arnau E, Karlberg AT, Lepoittevin JP (2000) Synthesis and allergenic potential of a 15-hydroperoxyabietic acid-like model: Trapping of radical intermediates. Chem Res Toxicol 13:1028-1036.
20. Giménez-Arnau E, Haberkorn L, Grossi L, Lepoittevin JP (2002) Identification of alkyl radicals derived from an allergenic cyclic tertiary allylic hydroperoxide by combined use of radical trapping and ESR studies. Tetrahedron 58: 5535-5545.
21. Bertrand F, Basketter DA, Roberts DW, Lepoittevin J-P (1997) Skin sensitization to eugenol and isoeugenol in mice: possible metabolic pathways involving ortho-quinone and quinone methide intermediates. Chem Res Toxicol 10: 335-343.
22. Merk HF (1997) Skin metabolism. In: Lepoittevin JP, Basketter DA, Goossens A, Karlberg AT (eds) Allergic contact dermatitis: The molecular basis. Springer, Berlin, pp 68-80.
23. Dupuis G (1979) Studies of poison ivy. In vitro lymphocytes transformation by urushiol protein conjugates Brit J Dermatol 101:617-624.
24. Reynolds G, Rodriguez E (1981) Prenylated hydroquinones: contact allergens from trichomes of Phacelia minor and P. parryi. Phytochemistry 20:1365-1366.
25. Bergmann HH, Beijersbergen JCH, Overeem JC, Sijpesteijn AK (1967) Isolation and identification of a-methylene-gbutyrolactone: A fungitoxic substance from tulips. Recueil des Travaux Chimiques des Pays-Bas 86:709-713.
26. Landsteiner K, Jacobs JL (1936) Studies on the sensitization of animals with simple chemicals. J Exp Med 64:625-639.
27. Dupuis G, Benezra C (1982) Allergic contact dermatitis to simple chemicals. Marcel Dekker, New York.
28. Hellerström S, Thyresson N, Blohm SG, Widmark G (1955) On the nature of eczematogenic component of oxidized D3- carene. J Invest Dermatol 24:217-224.
29. Karlberg AT (1988) Contact allergy to colophony. Chemical identification of allergens. Sensitization experiments and clinical experiments. Acta Dermato-Venereol 68(suppl 139):1-43.
30. Karlberg AT, Shao LP, Nilsson U, Gäfvert E, Nilsson JLG (1994) Hydroperoxides in oxidized d-limonene identified as potent contact allergens. Arch Dermatol Res 286:97-103.
31. Stampf JL, Benezra C, Klecak G, Geleick H, Schulz KH, Hausen B (1982) The sensitization capacity of helenin and two of its main constituents, the sesquiterpene lactones, alantolactones and isoalantolactone. Contact Derm 8:16-24.
32. Baer RL (1954) Cross-sensitization phenomena. In: Mackenna (ed). Modern trends in dermatology. Butterworth, London, pp 232-258.
33. Benezra C, Maibach H (1984) True cross-sensitization, false cross-sensitization and otherwise. Contact Derm 11:65-69.
34. Cohen NC, Blaney JM, Humblet C, Gund P, Barry DC (1990) Molecular modeling software and methods for medicinal chemistry. J Med Chem 33:883-984.
35. Coopman S, Degreef H, Dooms-Goossens A (1989) Identification of cross-reaction patterns in allergic contact dermatitis from topical corticosteroids. Brit J Dermatol 121:27-34.
36. Lepoittevin JP, Drieghe J, Dooms-Goossens A (1995) Studies in patients with corticosteroid contact allergy: understanding cross-reactivity among different steroids. Arch Dermatol 131:31-37.
37. Roberts DW, Williams DL (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.
38. Fraginals R, Roberts DW, Lepoittevin J-P, Benezra C (1991) Refinement of the relative alkylation index (RAI) model for skin sensitization and application to mouse and guinea-pig test data for alkylsulfonates. Arch Dermatol Res 283: 387-394.
39. Franot C, Roberts DW, Basketter DA, Benezra C, Lepoittevin J-P (1994) Structure-activity relationships for contact allergenic potential of g, g-dimethyl-g-butyrolactone derivatives Part II. Chem Res Toxicol 7:307-312.
40. Roberts DW, Basketter DA (1997) Further evaluation of the quantitative structure-activity relationship for skin-sensitizing alkyl transfer agents. Contact Derm 37:107-112.
41. Roberts DW, Basketter DA (2000) Quantitative structureactivity relationships: sulfonate esters in the local lymph node assay. Contact Derm 42:154-161.
42. Basketter DA, Gerberick GF, Kimber I, Loveless SE (1996) The local lymph node assay: A viable alternative to currently accepted skin sensitization tests. Food Chem Toxicol 34: 985-997.
43. Basketter DA, Lea LJ, Dickens A et al (1999) A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose-response. J Appl Toxicol 19:261-266.
44. Perrin DD, Dempsey B, Serjeant EP (1981) pKa prediction for organic acids and bases. Chapman and Hall, London, pp 109-126.
45. Patlewicz GY, Wright ZM, Basketter DA, Pease CK, Lepoittevin JP, Gimenez-Arnau E (2002) Structure-activity relationships for selected fragrance allergens. Contact Derm 47:219-226.
46. Barbier A, Rizova E, Stampf J-L, Lacheretz F, Pistor FHM, Bos JD, Kapsenberg ML, Becker D, Mohamadzadeh M, Knop J, Mabic S, Lepoittevin J-P (1994) Development of a predictive in vitro test for detection of sensitizing compounds (European BRIDGE project). In: Rougier A, Goldberg AM, Maibach HI (eds) In vitro skin toxicology (irritation, phototoxicity, sensitization). Liebert, New York, pp 341-350.
47. Gerberick F, Vassallo J, Bailey R, Morrall S, Lepoittevin J-P (2004) Development of peptide reactivity assay for screening allergens. Toxicol Sci 81:332-343.
48. Gerberick F, Vassallo J, Foertsch L, Price B, Chaney J, Lepoittevin J-P (2007) Quantification of chemical peptide reactivity for screening contact allergens. Toxicol Sci 97: 417-427.
49. Levin CY, Maibach HI (2008) Animal, human, and in vitro test methods for predicting skin irritation. In: Zhai H, Maibach HI (eds) Dermatotoxicology, 7th edn. CRC press, Boca Raton, pp 383-389.
50. Kang KW, Lee SJ, Kim SG (2005) Molecular mechanism of nrf2 activation by oxidative stress. Antioxid Redox Signal 7(11-12):1664-1673.
51. Natsch A, Emter R (2008) Skin sensitizers induce antioxidant response element dependent genes: Application to the In Vitro testing of the sensitization potential of chemicals. Toxicol Sci 102:110-119.
52. Lepoittevin JP, Basketter DA, Goossens A, Karlberg AT (eds) (1997) Allergic contact dermatitis: The molecular basis. Springer, Berlin.
53. Dupuis G, Benezra C (1982) Allergic contact dermatitis to simple chemicals. Marcel Dekker, New York.
54. Smith CK, Hotchkiss SAM (2001) Allergic contact dermatitis: chemical and metabolic mechanisms. Taylor & Francis, London, New York.