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Structure‐activity relationships in allergic contact dermatitis
Author(s) -
Hausen B. M.,
Hettsch H.,
Borrman B.,
Koch D.,
Rathmann R.,
Richter B.,
König W. A.
Publication year - 1995
Publication title -
contact dermatitis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.524
H-Index - 96
eISSN - 1600-0536
pISSN - 0105-1873
DOI - 10.1111/j.1600-0536.1995.tb00440.x
Subject(s) - chemistry , side chain , potency , primulaceae , carbon chain , allergic contact dermatitis , stereochemistry , sensitization , alkyl , organic chemistry , allergy , botany , polymer , biochemistry , biology , immunology , in vitro
Primin (2‐methoxy‐6‐pentyl‐1,4‐benzoquinone)is a naturally‐occurring strong sensitizer from Primula obconica (Primulaceae), To determine the effect of side‐chain length on senstizing potency 15 analogues with linear side chains from to from C 1 , to C 15 and 4 C 6 ‐ analogues with branched side chains were prepared synthetically and devoted to experimental sensitization in guinea pigs The results showed an increase of the sensitizing capacity with increasing length of the alkyl side chain from C 1 to C 10 , reaching a maximum at C 11 and C 12 . On further elongation the senstizing potency decreased beyond C 13 reaching values which finally were as low as those of the C 1 and C 3 derivatives. The results mirror finding which finally were as low as those of the C 1 and C 3 derivatives. The results mirror findings which formerly have been obtained with other non‐quinonoid compounds like catechols, phenols hydroquinones and gallates. In the plant kingdom. Compound approximating an “ideal allergen” consisting of a quinonoid ring with a 10 or 11 carbon‐remarkably strong sensitizer found in Wigandia caracasana (Hydrophyllaceae)