Double-headed haptens with pyrocatechol (poison ivy like) and methylene lactone functional groups: a search for skin-tolerance inducers

J Med Chem. 1987 Jan;30(1):165-8. doi: 10.1021/jm00384a027.

Abstract

In order to develop new theories for desensitization, a potential skin sensitizer, 1, with two different haptenic ends, a pyrocatechol group and an alpha-methylene-gamma-butyrolactone moiety, separated by a straight nine-carbon-atom chain has been prepared and used to sensitize guinea pigs. A "monohapten" 8 containing an electrophylic alpha-methylene-gamma-butyrolactone, connected to a dimethoxybenzene group, has also been prepared. Both the "bihapten" 1 and the "monohapten" 8 were shown to be sensitizers. Bihapten 1 sensitized animals recognized only bihapten 1 (and not the lactone 8) while monohapten 8 sensitized guinea pigs reacted to both 8 and 1. Bihapten 1 treated animals were further sensitized to monohapten 8 and challenged to the latter: the skin intensity reaction was significantly lower than the test to 8 in 8-sensitized animals. Bihapten 1 seems therefore to "tolerize" against the alpha-methylene-gamma-butyrolactone end.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Catechols / chemical synthesis*
  • Catechols / immunology
  • Dermatitis, Contact*
  • Female
  • Guinea Pigs
  • Haptens*
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Lactones / immunology
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship

Substances

  • Catechols
  • Haptens
  • Indicators and Reagents
  • Lactones