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Stereospecificity in allergic contact dermatitis to simple substituted methylene lactone derivatives.

Abstract
The enantiomers of beta,gamma-dimethyl- and beta-methyl-alpha-methylene-gamma-butyrolactones have been synthesized stereospecifically from glutamic acid and beta-hydroxy isobutyric acid, respectively. Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them. Both enantiomers of beta-methyl lactone as well as (+)-beta,gamma-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-beta,gamma-dimethyl lactone showed no specificity. An interpretation is proposed.
AuthorsH Mattes, K Hamada, C Benezra
JournalJournal of medicinal chemistry (J Med Chem) Vol. 30 Issue 11 Pg. 1948-51 (Nov 1987) ISSN: 0022-2623 [Print] United States
PMID3669003 (Publication Type: Journal Article)
Chemical References
  • Allergens
  • Furans
  • 4-Butyrolactone
Topics
  • 4-Butyrolactone (immunology)
  • Allergens
  • Animals
  • Dermatitis, Contact (etiology)
  • Female
  • Furans (immunology)
  • Guinea Pigs
  • Skin Tests
  • Stereoisomerism
  • Structure-Activity Relationship

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