Skip to main content
SpringerLink
Log in

Molecular Aspects of Allergic Contact Dermatitis

  • Chapter
Textbook of Contact Dermatitis

Abstract

It is now generally accepted that contact allergens (haptens) must have special properties in order to be sensitizing. Among these properties, the most important appears to be the faculty of reacting with epidermal proteins, giving a complete allergen [1, 2]. The most economical way of looking at the nature of the carrier protein is to consider that membrane-embedded proteins are the most likely candidates. Protein groups capable of forming strong covalent bonds with a hapten are nucleophilic groups, -Nu-H, where Nu (= nucleophile) stands for S- or NH-. They can react with electrophiles to produce the antigen, a modified protein:

protein-Nu-H + hapten → protein-Nu-hapten.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Landsteiner K, Jacobs JL (1936) Studies on the sensitization of animals with simple chemicals. III. J Exp Med 64: 625–639

    Google Scholar 

  2. Dupuis G, Benezra C (1982) Allergic contact dermatitis to simple chemicals: a molecular approach. Dekker, New York

    Google Scholar 

  3. Roberts DW, Williams DL (1982) The derivation of quantitative correlations between skin sensitization and physico-chemical parameters for alkylating agents and their application to experimental data for sultones. J Theor Biol 99: 807–825

    Article  PubMed  CAS  Google Scholar 

  4. Kligman AM (1958) Poison ivy (Rhus) dermatitis. Arch Dermatol 77: 149

    Article  CAS  Google Scholar 

  5. Benezra C, Ducombs G, Sell Y, Foussereau J (1985) Plant contact dermatitis. St Louis Decker/Mosby, TorontoN, pp 72–79

    Google Scholar 

  6. Lepoittevin JP, Benezra C (1986) Saturated analogs of poison ivy allergens. Synthesis of trans, trans-and cis, trans-3-alkyl-l,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis. J Med Chem 29: 287–291

    Article  PubMed  CAS  Google Scholar 

  7. Benezra C, Sigman CC, Perry LR, Helmes CT, Maibach HI (1985) A systematic search for structure-activity relationships of skin contact sensitizers: methodology, J Invest Dermatol 85: 351–356

    Article  PubMed  CAS  Google Scholar 

  8. Benezra C, Sigman CC, Bagheri D, Helmes CT, Maibach HI (1989) A systematic search for structure-activity relationships of skin contact sensitizers. II. Paraphenylenediamines. Semin Dermatol 8: 88–93

    PubMed  CAS  Google Scholar 

  9. Mayer RL (1950) Compounds of quinone structures as allergens and cancerogenic agents. Experiential 6: 241–280

    Article  CAS  Google Scholar 

  10. Basketter DA, Goodwin BFJ (1988) Investigation of the prohapten concept. Cross-reactions between 1,4-benzene derivatives in the guinea pig. Contact Dermatitis 19: 248–253

    Article  PubMed  CAS  Google Scholar 

  11. Dossou KG, Sicard C, Kalopissis G, Schaefer H (1985) Methods for assessment of experimental allergy in guinea-pigs adapted to cosmetic ingredients. Contact Dermatitis 13: 226–234

    Article  PubMed  CAS  Google Scholar 

  12. Haustein UF, Tegetmeyer L, Ziegler V (1985) Allergic and irritant potential of benzoyl peroxide. Contact Dermatitis 13: 252–257

    Article  PubMed  CAS  Google Scholar 

  13. National Toxicology Program (NTP) (1986) Carcinogenesis Studies of ethyl acrylate (CAS 140–88–5) in F344 rats and B6C3F1 mice (Gavage studies). Public Health Service, National Institutes of Health, U.S. Department of Health and Human Services, Washington (Technical report 259 )

    Google Scholar 

  14. International Agency for Research on Cancer (IARC) (1985) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: ally! compounds, aldehydes, epoxides, and peroxides, vol 36. IARC, Lyon, pp 101–132

    Google Scholar 

  15. Stotts J, Ely J (1977) Induction of human skin sensitization to ethanol. J Invest Dermatol 69: 219–222

    Article  PubMed  CAS  Google Scholar 

  16. Foussereau J, Benezra C, Maibach HI (1982) Occupational contact dermatitis: clinical and chemical aspects, Munksgaard, Copenhagen, pp 229–230

    Google Scholar 

  17. Kurokawa Y, Takamura N, Matsushima Y, Imazawa T, Hayashi Y (1984) Studies on the promoting and complete carcinogenic activities of some oxidizing chemicals in skin carcinogenesis. Cancer Lett 24: 299–304

    Article  PubMed  CAS  Google Scholar 

  18. Ito N, Hagiwara A, Shibata M, Ogiso P, Fukushima S (1982) Induction of squamous cell carcinoma in the forestomach of F344 rats treated with butylated hydroxyanisole. Jpn J Cancer Res 73: 332–334

    CAS  Google Scholar 

  19. Ito N, Fukushima S, Hagiwara A, Shibata M, Ogiso T (1983) Carcinogenicity of butylated hydroxyanisole in F344 rats. J Natl Cancer Inst 70: 343–352

    PubMed  CAS  Google Scholar 

  20. Meynadier J-M, Meynadier J, Colmar A, Castelain PI, Ducombs G, Chabeau G, LaCroix M, Martin P, Ngangu Z (1982) Allergie aux conservateurs. Acta Dermatol Venereol (Stockh) 109: 1017–1023

    CAS  Google Scholar 

  21. Ito N, Ogiso T, Fukushima S, Shibata M, Hagiwara A (1984) Carcinogenicity of captafol in B6C3F1 mice. Gann 75: 853–65

    PubMed  CAS  Google Scholar 

  22. Lisi P, Caraffini S, Assalve D (1987) Irritation and sensitization potential of pesticides. Contact Dermatitis 17: 212–218

    Article  PubMed  CAS  Google Scholar 

  23. De Groot AC, Bos JD, Jagtman BA, Bruynzeel DP, van Joost T, Weyland JW (1986) Contact allergy to preservatives II. Contact Dermatitis 15: 218–222

    Article  PubMed  Google Scholar 

  24. Lisi P, Caraffini S, Assalve D (1986) A test series for pesticide dermatitis. Contact Dermatitis 15: 266–269

    Article  PubMed  CAS  Google Scholar 

  25. National Cancer Institute (NCI) (1977) Bioassay of captan for possible carcinogenicity. Public Health Service, National Institutes of Health, Department of Health, Education, and Welfare, Washington (Technical report no 15 )

    Google Scholar 

  26. Bruynzeel DP, van Ketel WG (1986) Contact dermatitis due to chlorothalonil in floriculture. Contact Dermatitis 14: 67–68

    Article  PubMed  CAS  Google Scholar 

  27. National Cancer Institute (NCI) (1978) Bioassay of chlorothalonil for possible carcinogenicity. Public Health Service, National Institutes of Health, Department of Health, Education, and Welfare, Washington (Technical report no 41 )

    Google Scholar 

  28. International Agency for Research on Cancer (IARC) (1976) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some naturally occurring substances, vol 10. IARC, Lyon, pp 113–119

    Google Scholar 

  29. Foussereau J, Benezra C, Maibach HI (1982) Occupational contact dermatitis: clinical and chemical aspects. Munksgaard, Copenhagen, p 40

    Google Scholar 

  30. Foussereau J, Benezra C, Maibach H (1982) Occupational contact dermatitis: clinical and chemical aspects. Munksgaard, Copenhagen, p 221

    Google Scholar 

  31. International Agency for Research on Cancer (IARC) (1976) IARC monographs on the evaluation of the carcinogenic risk chemicals to humans: cadmium, nickel, some epoxides, miscellaneous industrial chemicals and general consideration on volatile anesthetics, vol 11. IARC, Lyon, pp 131–140

    Google Scholar 

  32. Wester PW, Van der Heijden CA, Bisschop A, Van Esch GJ (1985) Carcinogenicity study with epichlorohydrin ( CEP) by gavage in rats. Toxicology 36: 325–339

    Google Scholar 

  33. Fregert S (1978) Allergic contact dermatitis from ethylacrylate in a window sealant. Contact Dermatitis 4: 56

    Article  PubMed  CAS  Google Scholar 

  34. International Agency for Research on Cancer (IARC) (1974) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some anti-thyroid and related substances, nitrofurans and industrial chemicals, vol 7. IARC, Lyon, pp 45–52

    Google Scholar 

  35. Innes JRM, Ulland B, Valerio MG, Petrucelli L, Fishbein L, Hart ER, Pallotta AJ, Bates RR, Falk HL, Gart JJ, Klein M, Mitchell I, Peters J (1969) Bioassay of pesticides and industrial chemicals for tumorigenicity in mice: a preliminary note. J Natl Cancer Inst 42: 1101–1114

    PubMed  CAS  Google Scholar 

  36. Weisburger EK, Ulland BM, Nam J-M, Gart JJ, Weisburger JH (1981) Carconogenicity tests of certain environmental and industrial chemicals. J Natl Cancer Inst 67: 75–88

    PubMed  CAS  Google Scholar 

  37. Albert RE, Sellakumar AR, Laskin S, Kuschner M, Nelson N, Snyder CA (1982) Gaseous formaldehyde and hydrogen chloride induction of nasal cancer in the rat. J Natl Cancer Inst 68: 597–603

    PubMed  CAS  Google Scholar 

  38. International Agency for Research on Cancer (IARC) (1982) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some industrial chemicals and dyestuffs, vol 29. IARC, Lyon, pp 345–390

    Google Scholar 

  39. Ormerod, AD, Main RA (1985) Sensitisation to “sensitive teeth” toothpaste. Contact Dermatitis 13: 192–193

    Article  PubMed  CAS  Google Scholar 

  40. International Agency for Research on Cancer (IARC) (1974) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some aromatic amines, hydrazine and related substances, N-nitroso compounds and miscellaneous alkylating agents, vol 4. IARC, Lyon, pp 127–136

    Google Scholar 

  41. Wrangsjo K, Maartensson A (1986) Hydrazine contact dermatitis from gold plating. Contact Dermatitis 15: 244–245

    Article  PubMed  CAS  Google Scholar 

  42. International Agency for Research on Cancer (IARC) (1980) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some pharmaceutical drugs, vol 24. IARC, Lyon, pp 185–194

    Google Scholar 

  43. Mitchell JC, Maibach HI (1975) Allergic contact dermatitis from phenoxybenzamine hydrochloride: cross-sensitivity to some related haloalkylamine compounds. Contact Dermatitis 1: 363–366

    Article  PubMed  CAS  Google Scholar 

  44. National Cancer Institute (NCI) (1980) Bioassay of phenoxybenzamine hydrochloride for possible carcinogenicity. Public Health Service, National Institutes of Health, Department of Health, Education, and Welfare, Washington (Technical report no 72 )

    Google Scholar 

  45. Hiraga K, Fujii T (1984) Induction of tumours of the urinary bladder in F344 rats by dietary administration of o-phenylphenol. Food Chem Toxicol 22: 865–870

    Article  PubMed  CAS  Google Scholar 

  46. Van Hecke E (1986) Contact sensitivity to o-phenylphenol in a coolant. Contact Dermatitis 15: 46

    Article  Google Scholar 

  47. Dunkelberg H (1982) Carcinogenicity of ethylene oxide and 1,2-propylene oxide upon intragastric administration to rats. Br J Cancer 46: 924–933

    Article  PubMed  CAS  Google Scholar 

  48. International Agency for Research on Cancer (IARC) (1976) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some anti-thyroid and related substances, nitrofurans and industrial chemicals, vol 7. IARC, Lyon, pp 191–200

    Google Scholar 

  49. Kuper CF, Reuzel PG, Feron VJ, Verschuuren H (1988) Chronic inhalation toxicity and carcinogenicity study of propylene oxide in Wistar rats. Food Chem. Toxicol 26: 159–167

    Google Scholar 

  50. Van Ketel WG (1979) Contact dermatitis from propylene oxide. Contact Dermatitis 5: 191–192

    Article  PubMed  Google Scholar 

  51. National Toxicology Program (NTP) (1985) Carcinogenesis studies of propylene oxide (CAS no 75–56–9) in F344 Rats and B6C3F1 mice (inhalation studies). Public Health Service, National Institutes of Health, U.S. Department of Health and Human Services, Washington (Technical report no 267 )

    Google Scholar 

  52. International Agency for Research on Cancer (IARC) (1979) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some monomers, plastics and synthetic elastomers, and acrolein, vol 19. IARC, Lyon, pp 231–284

    Google Scholar 

  53. Sjoborg S, Fregert S, Trulsson L (1984) Contact allergy to styrene and related chemicals. Contact Dermatitis 10: 94–96

    Article  PubMed  CAS  Google Scholar 

  54. International Agency for Research on Cancer (IARC) (1974) IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: some anti-thyroid and related substances, nitrofurans and industrial chemicals, vol 7. IARC, Lyon, pp 95–110

    Google Scholar 

  55. Kellett JK, Beck MH, Auckland G (1984) Contact sensitivity to thiourea in photocopy paper. Contact Dermatitis 11: 124

    Article  PubMed  CAS  Google Scholar 

  56. Estlander T, Jolanki R, Kanerva L (1986) Dermatitis and urticaria from rubber and plastic gloves. Contact Dermatitis 14: 20–25

    Article  PubMed  CAS  Google Scholar 

  57. National Toxicology Program (NTP) (1983) Carcinogenesis studies of ziram (CAS no 137–30–4) in F344 rats and B6C3F1 mice. Public Health Service, National Institutes of Health, U.S. Department of Health and Human Services, Washington (Technical report no 238 )

    Google Scholar 

Download references

Authors
  1. Jean-Pierre Lepoittevin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Claude Benezra
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Caroline C. Sigman
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Donya Bagheri
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rossana Fraginals
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Howard I. Maibach
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. St. John’s Institute of Dermatology, St. Thomas’s Hospital, SE1 7EH, London, UK

    Richard J. G. Rycroft

  2. Department of Dermatology, Gentofte Hospital, University of Copenhagen, Niels Andersens Vej 65, 2900, Hellerup, Denmark

    Torkil Menné

  3. Hautklinik der Städtischen Kliniken Dortmund, Abteilung Dermatologie, Universität Witten/Herdecke, Beurhausstraße 40, 44123, Dortmund, Germany

    Peter J. Frosch

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Lepoittevin, JP., Benezra, C., Sigman, C.C., Bagheri, D., Fraginals, R., Maibach, H.I. (1995). Molecular Aspects of Allergic Contact Dermatitis. In: Rycroft, R.J.G., Menné, T., Frosch, P.J. (eds) Textbook of Contact Dermatitis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-03104-9_7

Download citation

  • DOI: https://doi.org/10.1007/978-3-662-03104-9_7

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-03106-3

  • Online ISBN: 978-3-662-03104-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation