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Active Oxygen Species and Structure Specificity of Antipsoriatic Anthrones
Author(s) -
Müller Klaus
Publication year - 1988
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19883210703
Subject(s) - dithranol , anthrone , chemistry , active oxygen , radical , moiety , anthracene , stereochemistry , oxygen , active site , biological activity , organic chemistry , psoriasis , biochemistry , enzyme , medicine , dermatology , in vitro
Twenty‐one analogues of the antipsoriatic compound dithranol were tested for their capability to produce 1 O 2 and O 2 .‐ . A correlation was found between the production of active oxygen species and the minimum structure for the antipsoriatic activity of anthrone derivatives. The ability of the anthrones to sensitize the formation of 1 O 2 is a function of the deprotonated hydroxyl group at C‐1 associated with the carbonyl group at C‐9 of the anthracene molecule; the CH 2 ‐moiety at C‐10 initiates the formation of free radicals and is responsible for the production of O 2 .‐ , which is prevented by substitution of the hydrogen atoms at C‐10. Since only the active compounds dithranol, chrysarobin, frangulaemodin‐anthrone and aloeemodin‐anthrone produce 1 O 2 as well as O 2 .‐ , the therapeutic effectiveness of the anthrones appears to be due to both active oxygen species.