Activity of coumarin–oxadiazole-appended phenol in inhibiting DNA oxidation and scavenging radical

Abstract

Fourteen coumarin–oxadiazole-appended phenols were synthesized, while halogen atom, methoxyl, and hydroxyl groups acted as the functional groups for testing the ability to trap 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+) and to inhibit the oxidation of DNA caused by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) and Cu2+/glutathione (GSH). The coumarin–oxadiazole-appended phenols containing the hydroxyl group were able to inhibit AAPH-induced oxidation of DNA and to quench ABTS+, and the antioxidant effectiveness depended upon the number of hydroxyl groups. Moreover, the coumarin–oxadiazole-appended phenols used herein were able to inhibit Cu2+/GSH-induced oxidation of DNA, and the inhibitory effect generated by bromide was similar to that of the hydroxyl group. In particular, the antioxidant effectiveness of para-bromide at the benzene ring even approached to that of Trolox.