Skip to main content

Hapten-Protein Interactions

  • Chapter
Allergic Contact Dermatitis

Abstract

The skin sensitization reaction to a chemical is a multistep process with two principal stages:

  1. 1.

    A state of sensitization to the chemical is induced. This may be on first exposure to the chemical or only after many exposures.

  2. 2.

    A sensitization response is elicited. This happens when a subject sensitive to a given chemical is exposed to, or challenged with, the same chemical.

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

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

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.

Similar content being viewed by others

References

  1. Baer H, Watkins RC, Kurtz AP, Byck JS, Dawson CR (1967) Delayed contact sensitivity to catechols. J Immunol 99:307–375

    Google Scholar 

  2. Corbett MD, Billets S (1975) Characterization of poison oak urushiol. J Pharm Sci 64: 1715

    Article  PubMed  CAS  Google Scholar 

  3. Landsteiner K, Jacobs J (1936) Studies on the sensitization of animals with simple chemical compounds. J Exp Med 64:625–639

    Article  PubMed  CAS  Google Scholar 

  4. Roberts DW, Goodwin BFJ, Williams DL, Jones K, Johnson AW, Alderson JCE (1984) Correlation between skin sensitization potential and chemical reactivity for nitrobenzyl compounds. Food Chem Toxicol 21:811–813

    Google Scholar 

  5. Swain CG, Scott CB (1953) Quantitiative correlation of reaction rates. Comparison of hydroxide ion with other nucleophilic reagents towards alkyl halides, esters, epoxides and acyl halides. J Am Chem Soc 75:141–147

    Google Scholar 

  6. Pearson RG, Sobel H, Songstad J (1968) Nucleophilic reactivity constants toward methyl iodide and trans-[Pt(py)2Cl2]. J Am Chem Soc 90:319–326

    Article  CAS  Google Scholar 

  7. Koskikallio J (1969) Nucleophilic reactivity. II. Kinetics of reactions of methyl per- chlorate with nucleophiles in water. Acta Chem Scand 23:1477–1489

    Article  CAS  Google Scholar 

  8. Lepoittevin JP, Benezra C (1992) 13C-Enriched methyl alkane sulphonates: new lipophilic methylating agents for the identification of nucleophilic amino acids of protein by NMR. Tetrahedron Lett 33:3875–3878

    Article  CAS  Google Scholar 

  9. Liberato DJ, Byers VS, Ennick RGD, Castagnoli N jr (1981) Regiospecific attack of nitrogen and sulphur nucleophiles on quinones derived from poison oak/ivy catechols (urus- hiols) and analogues as models for urushiol-protein conjugate formation. J Med Chem 24:28–33

    Article  PubMed  CAS  Google Scholar 

  10. Stampf JL, Benezra C, Byers V, Castagnoli N jr (1986) Induction of tolerance to poison ivy in the guinea pig by cutaneous application of the structural analog 5-methyl-3-n-penta- decylcatechol. J Invest Dermatol 5:535–538

    Article  Google Scholar 

  11. Foussereau J, Benezra C (1970) Les eczémas allergiques professionels. Masson, Paris

    Google Scholar 

  12. Rycroft RGJ (1981) Allergic contact dermatitis from laboratory synthesis of 4-bromo- methyl-6,8-dimethyl-2(lH)-quinolone. Contact Dermatitis 7:39–42

    Article  PubMed  CAS  Google Scholar 

  13. Roberts DW, Basketter DA (1990) A quantitative structure-activity/dose-response relationship for contact allergic potential of alkyl group transfer agents. Contact Dermatitis 23:331–335

    Article  PubMed  CAS  Google Scholar 

  14. Fraginals R, Lepoittevin JP, Benezra C (1990) Sensitizing capacity of three methyl alkane- sulphonates: a murine in vivo and in vitro model of allergic contact dermatitis. Arch Dermatol Res 282:455–458

    Article  PubMed  CAS  Google Scholar 

  15. Roberts DW (1995) Linear free energy relationships for reactions of electrophilic halo- and pseudohalobenzenes, and their application in prediction of skin sensitization potential for SNAr electrophiles. Chem Res Toxicol 8:545–551

    Article  PubMed  CAS  Google Scholar 

  16. Jordan WP jr, Bourlas MC(1975) Allergic contact dermatitis to underwear elastic. Arch Dermatol 111:593–595

    Article  PubMed  CAS  Google Scholar 

  17. Lawless JF, Stubbs SS (1978) Comparative efficacy of once-a-day diflorasone diacetate and TID hydrocortisone in treating eczematous dermatitis. Curr Ther Res 23:159

    Google Scholar 

  18. Schirren CG (1951) Diacetyl, ein im Tabakrauch, Holzrauch und Kaffeearoma enthalte- nes Allergen. Hautarzt 2:324–325

    Google Scholar 

  19. Bundgaard H (1990) The possible implication of steroid-glyoxal degradation products in allergic reactions to corticosteroids. Arch Pharm Chem Sci Ed 8:83–90

    Google Scholar 

  20. Majeti VA, Suskind RR (1977) Mechanism of cinnamaldehyde sensitization. Contact Dermatitis 3:16–18

    Article  PubMed  CAS  Google Scholar 

  21. Benezra C, Ducombs G (1987) Molecular aspects of allergic contact dermatitis to plants. Derm Beruf Umwelt 35:4–11

    PubMed  CAS  Google Scholar 

  22. Slob A (1973) Tulip allergens in Alstroemeria and some other Liliflora. Phytochemistry 12:811–815

    Article  CAS  Google Scholar 

  23. Rodriguez E, Towers GHN, Mitchell JC (1976) Biological activities of sesquiterpene lactones. Phytochemistry 15:1573–1580

    Article  CAS  Google Scholar 

  24. Hausen B, Schmalle HW (1985) Structure-activity apects of 4 allergenic sesquiterpene lactones lacking the exocyclic «-methylene at the lactone ring. Contact Dermatitis 13: 329–332

    Article  PubMed  CAS  Google Scholar 

  25. Schlewer G, Stampf JL, Benezra C (1980) Synthesis of a-methylene-y-butyrolactones: a structure-activity relationship study of their allergenic power. J Med Chem 23: 1031–1038

    Article  PubMed  CAS  Google Scholar 

  26. Subba Rao PV, Mangala A, Towers GHN, Rodriguez E (1978) Immunological activity of parthenin and its diastereomer in persons sensitized by Parthenium hysterophorus L. Contact Dermatitis 4:199–203

    Article  Google Scholar 

  27. Thormann J, Hansen I, Misfeldt J (1985) Occupational dermatitis from butyl maleinate. Contact Dermatitis 13: 314–316

    Article  PubMed  CAS  Google Scholar 

  28. Reynolds GW, Epstein WL, Rodriguez E (1986) Urushiol contact allergens from plants in the family Hydrophyllaceae. Contact Dermatitis 14:39–48

    Article  PubMed  CAS  Google Scholar 

  29. Marchand B, Benezra C (1982) Double-head haptens. Synthesis and experimentally induced contact sensitivity to substances containing two related haptens, pyrocatechol and a-methylene-y-butyrolactone. J Med Chem 30:165–168

    Google Scholar 

  30. Nazih A, Benezra C, Lepoittevin JP (1993) Bihaptens with 5- and 6-methyl-substituted alkylcatechols and methylene lactone functional groups: tools for hapten (allergen or tolerogen)-protein interaction studies. Chem Res Toxicol 6:215–222

    Article  PubMed  CAS  Google Scholar 

  31. Hellerstrom S, Thyresson N, Widmark G (1957) Chemical aspects of turpentine eczema. Dermatologica 115:277–286

    Article  PubMed  CAS  Google Scholar 

  32. Foussereau J, Samsoen M, Hecht MT (1983) Occupational dermatitis to Ampholyt G in hospital personnel. Contact Dermatitis 9:233–234

    Article  PubMed  CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  34. Ashby J, Hilton J, Dearman RJ, Callander RD, Kimber I (1993) Mechanistic relationship among mutagenicity, skin sensitization and skin carcinogenicity. Environ Health Perspect 101:62–67

    Article  PubMed  CAS  Google Scholar 

  35. Wahlberg J et al (1992) Cross reactivity to palladium and nickel studied in the guinea pig. Acta Derm Venereol (Stockh) 72:95–97

    CAS  Google Scholar 

  36. Bal W, Lukszo J, Jezowska-Bojczuk M, Kasprzak KS (1995) Interaction of Ni(II) with histone. Stability and solution structure of complexes with Ac-Cys-Ala-Ile-His-NH2, a putative metal binding sequence of histone H3. Chem Res Toxicol 8:683–692

    Article  PubMed  CAS  Google Scholar 

  37. Romagnoli P, Labhardt AM, Sinigaglia F (1991) Selective interaction of Ni with an MHC- bound peptide. EMBO J 10:1303–1306

    PubMed  CAS  Google Scholar 

  38. Roberts DW, Williams DL (1983) Sultones as by-products in anionic surfactants. Com Jorn Com Esp Det 14:203–212

    Google Scholar 

  39. Roberts DW, Lawrence JG, Fairweather I A, Clemett CJ, Saul CD (1987) An investigation into the possibilities of formation of alk-l-ene-l,3-sultones in alpha olefin sulphonates (AOS). Com Jorn Com Esp Det 18:101–117

    CAS  Google Scholar 

  40. Bordwell EG, Osborne CE, Chapman RD (1959) Hydrolysis of sultones - effect of methyl groups on the rates of ring opening solvolyses. J Am Chem Soc 81:2698–2705

    Article  CAS  Google Scholar 

  41. Roberts DW, Williams DL (1990) Formation of sultones in olefin sulphonation. J Am Oil Chem Soc 67:1020–1027

    Article  CAS  Google Scholar 

  42. Franot C, Benezra C, Lepoittevin JP (1993) Synthesis and interaction studies of 13 labeled lactone derivatives with a model protein using 13C NMR. Bioorg Med Chem Lett 1: 389–397

    Article  CAS  Google Scholar 

  43. Franot C, Roberts DW, Smith RG, Basketter DA, Benezra C, Lepoittevin JP (1994) Structure-activity relationships for contact allergenic potential of y, y-dimethyl-y- butyrolactone derivatives. 1. Synthesis and electrophilic reactivity studies of a(o>-sub- stituted-alkyl)-y,y-dimethyl-y-butyrolactones and correlation of skin sensitization potential and cross-sensitization patterns with structure. Chem Res Toxicol 7: 297–306

    Article  PubMed  CAS  Google Scholar 

  44. Franot C, Roberts DW, Basketter DA, Benezra C, Lepoittevin JP (1994) Structure-activity relationships for contact allergenic potential of y, y-dimethyl- y-buty rolactone derivatives. 2. Quantitative structure-skin relationships for a-substituted a-methyl-y,y-dime- thyl-y-butyrolactones. Chem Res Toxicol 7:307–312

    Article  PubMed  CAS  Google Scholar 

  45. Hausen BM, Beyer W (1992) The sensitizing capacity of the antioxidants propyl, octyl and dodecyl gallate and some related gallic acid esters. Contact Dermatitis 26:253–258

    Article  PubMed  CAS  Google Scholar 

  46. Barratt MD, Basketter DA (1992) Possible origin of the skin sensitization potential of isoeugenol and related compounds. Contact Dermatitis 27:98–104

    Article  PubMed  CAS  Google Scholar 

  47. Loveless SE, Ladies GS, Gerberick GF, Ryon CA, Basketter DA, Scholes EW, House RV, Hilton J, Dearman RJ, Kimber I (1996) Further evaluation of the local lymph node assay in the final phase of an international collaborative trial. Toxicology 108:141–152

    Article  PubMed  CAS  Google Scholar 

  48. Bolton JL, Acay NM, Vukomanovic V (1985) Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrol. Chem Res Toxicol 7:443–450

    Article  Google Scholar 

  49. Iverson SL, Hu LQ, Vukomanovic V, Bolton JL (1995) The influence of thep-alkyl substi- tuent on the isomerisation of o-quinone to p-quinone methides: potential bioactivation mechanism for catechols. Chem Res Toxicol 8:537 - 544

    Google Scholar 

  50. Bertrand F, Basketter DA, Roberts DW, Lepoittevin JP (1997) Skin sensitization to eu- genol and isoeugenol in mice: possible metabolic pathways involving ortho-quinone and quinone methide intermediates. Chem Res Toxicol 10:335–343

    Article  PubMed  CAS  Google Scholar 

  51. Shehade SA, Beck MH, Hiller VF (1991) Epidemiological survey of standard series patch test results and observations on day 2 and day 4 readings. Contact Dermatitis 24:119–122

    Article  PubMed  CAS  Google Scholar 

  52. Karlberg A-T, Bergstedt E, Boman A, Bohlinder K, Liden C, Nilsson JLG, Wahlberg JE (1985) Is abietic acid the allergenic component of colophony? Contact Dermatitis 13: 209–215

    Article  PubMed  CAS  Google Scholar 

  53. Karlberg A-T (1991) Air oxidation increases the allergenic potential of tall-oil rosin. Colophony contact allergens also identified in tall-oil rosin. Am J Contact Dermatitis 2: 43–49

    Google Scholar 

  54. Karlberg A-T, Bohlinder K, Boman A, Hacksell U, Hermansson J, Jacobsson S, Nilsson JLG (1988) Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony. J Pharm Pharmacol 40:42–47

    Article  PubMed  CAS  Google Scholar 

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

    Google Scholar 

  56. Haynes RK, Vonwiller SC (1990) Iron(III) and Copper(II) catalysed transformations of fatty acid hydroperoxides: efficient generation of peroxy radicals with copper(II) trifluo- romethanesulphonate. J Chem Soc Chem Commun 1102–1104

    Google Scholar 

  57. Karlberg A-T, Shao LP, Nilsson U, Gafvert E, Nilsson JLG (1993) Hydroperoxides in oxidized d-limonene identified as potent contact allergens. Arch Dermatol Res 286:97–103

    Article  Google Scholar 

  58. Lepoittevin JP, Karlberg AT (1994) Interaction of allergenic hydroperoxides with proteins: a radical mechanism? Chem Res Toxicol 7:130–133

    Article  PubMed  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Roberts, D.W., Lepoittevin, JP. (1998). Hapten-Protein Interactions. In: Lepoittevin, JP., Basketter, D.A., Goossens, A., Karlberg, AT. (eds) Allergic Contact Dermatitis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-80331-4_6

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-80331-4_6

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-80333-8

  • Online ISBN: 978-3-642-80331-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics