caa a22 4500 465772935 CHVBK 20180323111934.0 cr unu---uuuuu 170327e19900101xx s 000 0 eng 10.1007/BF00505646 doi (NATIONALLICENCE)springer-10.1007/BF00505646 Are free radicals and not quinones the haptenic species derived from urushiols and other contact allergenic mono- and dihydric alkylbenzenes? The significance of NADH, glutathione, and redox cycling in the skin [Elektronische Daten] [R. Schmidt, L. Khan, L. Chung] Summary: The induction of allergic contact dermatitis to urushiols from poison ivy and related plants is generally believed to involve an initial oxidation event by which a protein-reactive quinone is formed. However, this does not readily account for the contact allergenicity of closely related mono- and dihydric alkylbenzenes such as the alkylphenols and alkylresorcinols which are not so easily oxidised to quinones in vitro. When the redox processes known to occur in living tissues are taken into consideration, a more plausible unifying mechanism involving the formation of protein-reactive radical species becomes apparent. Experiments described here examine the autoxidation of p-benzoquinone and various mono- and dihydric benzenes and alkylbenzenes, and their reactions with the diphenylpicrylhydrazyl radical, cysteine, glutathione, and NADH. We have also demonstrated that administration to mice of 2-oxo-4-thiazolidine carboxylate, a compound known to elevate intracellular glutathione levels, inhibits the irritancy and sensitising activity of 3-pentadecylphenol. This work suggests that redox cycling in the skin following penetration of allergenic mono- and dihydric alkylbenzenes initially depletes local levels of endogenous reducing equivalents such as glutathione and NADH; once depleted, further cycling results in the uncontrolled generation of radical species which may reasonably be expected to exhibit protein reactivity. Springer-Verlag, 1990 Allergic contact dermatitis nationallicence Monohydric alkylbenzenes nationallicence Dihydric alkylbenzenes nationallicence Quinols nationallicence Resorcinols nationallicence Catechols nationallicence Urushiols nationallicence Prohapten activation nationallicence NADH nationallicence Cysteine nationallicence Glutathione nationallicence Diphenylpicrylhydrazyl nationallicence 2-Oxo-4-thiazolidine carboxylate nationallicence Schmidt R. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut Khan L. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut Chung L. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut Archives of Dermatological Research Springer-Verlag 282/1(1990-01-01), 56-64 0340-3696 282:1<56 1990 282 403 https://doi.org/10.1007/BF00505646 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00505646 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Schmidt R. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut NATIONALLICENCE 700 1- Khan L. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut NATIONALLICENCE 700 1- Chung L. Welsh School of Pharmacy, UWCC, P.O. Box 13, CF1 3XF, Cardiff, UK aut NATIONALLICENCE 773 0- Archives of Dermatological Research Springer-Verlag 282/1(1990-01-01), 56-64 0340-3696 282:1<56 1990 282 403 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer