Synthesis and properties of new fluorescent nucleosides and oligodeoxynucleotides derived from 5-formyl-2'-deoxyuridine.

Abstract

5-Formyl-2'-deoxyuridine (fdUrd) is a product of the oxidation of thymidine and is known to induce mutation (A:T to G:C) in DNA. Therefore, a selective detection method for fdUrd is needed, but convenient methods have not been developed. We planned to develop a novel selective method to detect fdUrd in damaged DNA based on a specific fluorogenic derivatization of fdUrd using 2-aminothiophenol derivatives (ATs) as fluorogenic reagents. To achieve this goal, we first investigated the synthesis and fluorescence properties of some 5-(benzothiazol-2-yl)-2'-deoxyuridine derivatives (btdUrds). We also report the reaction between oligodeoxynucleotides (ODNs) containing fdUrd and ATs.