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Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy). In order to determine the relationship between sensitizing capacity and chemical structure the synthesis of 19 side-chain-modified analogues of primin was carried out. With each of these primin derivatives 10 guinea pigs were sensitized using a modified FCA-method (FCA = Freund’s complete adjuvant). Elicitation was done open epicutaneously with 0.001 molar concentrations. In these sensitization experiments 2-methoxy-6-alkyl-1,4-benzoquinones (chain length C 1 -C 15 ) showed ascending sensitizing potency with increasing number of the side chain carbon atoms reaching maximum activity at an alkyl chain of 10 to 11 carbons. Beyond this point a decrease of the sensitizing potency in correlation with a further prolongation of the side chain was observed.

Synthese von seitenkettenmodifizierten Analogen des Allergens Primin / Synthesis of Side-Chain-Modified Analogues of the Allergen Primin