Stereospecificity in allergic contact dermatitis to simple substituted methylene lactone derivatives.
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.
Mattes
H
H
Laboratoire de Dermato-Chimie, Université Louis Pasteur, CHU, Strasbourg, France.
Hamada
K
K
Benezra
C
C
D015107:4-Butyrolactone / Q000276:immunology*; D000485:Allergens; D000818:Animals; D003877:Dermatitis, Contact / Q000209:etiology*; D005260:Female; D005663:Furans / Q000276:immunology*; D006168:Guinea Pigs; D012882:Skin Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000485:Allergens; D005663:Furans; D015107:4-Butyrolactone