Modification by ferrocene: An approach to enhance antioxidant ability of ailanthoidol to protect DNA

Biochimie
Chao Zhao, Zai-Qun Liu

Abstract

Ailanthoidol is a benzofuran-type neolignan containing an alcoholic and a phenolic hydroxyl groups and can be synthesized following the description in a previous report. In this work, its antioxidant effect was estimated in the experimental system of 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that ailanthoidol can scavenge 1.5 radicals in protecting DNA against AAPH-induced oxidation. Moreover, a benzyl group was used to etherize the phenolic hydroxyl group of ailanthoidol, resulting in the formation of (E)-2-(4'-benzyloxy-3'-methoxyphenyl)-5-(3″-hydroxypropenyl)-7-methoxybenzofuran (BBF). However, BBF cannot protect DNA against AAPH-induced oxidation. This result demonstrated that the alcoholic hydroxyl group cannot play the antioxidative role in protecting DNA. Furthermore, a ferrocenyl group was used to substitute the alcoholic hydroxyl group, leading to the formation of (E)-1-ferrocenyl-3-(2'-(4″-hydroxy-3″-methoxyphenyl)-7'-methoxybenzofuran-5'-yl)prop-2-en-1-one (FBF). FBF can scavenge 2.0 radicals in protecting DNA against AAPH-induced oxidation. This result indicated that the antioxidant ability of FBF was higher than that of ailanthoidol. Finally, FBF and ailanthoidol were...Continue Reading

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Citations

Jan 31, 2016·European Journal of Medicinal Chemistry·Hai-Qi ZhangLi-Ping Sun
Apr 5, 2019·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Zai-Qun Liu

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