Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
Thirty-five alpha-methylene-gamma-butyrolactones have been prepared and their allergenic properties tested on the skin of guinea pigs experimentally sensitized to (a) alantolactone (1), (b) isoalantolactone (2), and (c) alpha-methylene-gamma-butyrolactone (3). The two first groups of animals cross-react to lactones containing 9 to 18 carbon atoms but not to smaller alpha-methylene-gamma-butyrolactones. Conversely, animals sensitized to alpha-methylene-gamma-butyrolactone react only with alpha-methylene-gamma-butyrolactones containing 6 and 7 carbon atoms. These results are discussed in relation with the allergic contact dermatitis mechanism.
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000485:Allergens / Q000138:chemical synthesis*; D000818:Animals; D003429:Cross Reactions; D003877:Dermatitis, Contact / Q000209:etiology; D005260:Female; D005663:Furans / Q000138:chemical synthesis*; D006168:Guinea Pigs; D012882:Skin Tests; D013329:Structure-Activity Relationship
D000485:Allergens; D005663:Furans; D015107:4-Butyrolactone