Bioorganic & Medicinal Chemistry Letters 2011-07-15

BODIPY-modified 2'-deoxyguanosine as a novel tool to detect DNA damages.

Takeji Takamura-Enya, Ryoko Ishii

Index: Bioorg. Med. Chem. Lett. 21 , 4206-4209, (2011)

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Abstract

BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-Fl to the 5' position of the deoxyribose moiety of 2'-deoxyguanosine. Although this compound has low fluorescence activity, when depurination by the action of alkylating reagents and dG oxidation by singlet oxygen occurred, the emission of strong fluorescence was observed. BODIPY-dG was found, therefore, to be a very useful tool for selectively detecting DNA damaging activity particularly in natural environmental extracts.Copyright © 2011 Elsevier Ltd. All rights reserved.