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We synthesized various substituted 8-styryl-2'-deoxyguanosine and 8-styryl-2'-deoxyadenosine derivatives. Among them only acetyl substituted 8-styryl-2'-deoxyguanosine analog 5b showed a remarkable solvatochromicity (Δλ(max)(em)=91 nm),that is, strong fluorescence at 477 nm in 1,4-dioxane, but in methanol the fluorescence was red shifted to 558 nm with very low intensity. Such environmentally sensitive solvatochromic fluorescent guanosine analogs may be useful as a sensor for investigating interactions of DNA with DNA binding proteins., (Copyright © 2010 Elsevier Ltd. All rights reserved.)

6-Nitro- and 8-nitro-5-deazaflavin derivatives have been found to enhance prominently the radiation-induced formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodGuo) at the expense of formation of 2,6-diamino-4-hydroxy-5-formamidopyrimidine nucleosides (FapydGuo) both in deaerated and in N(2)O saturated aqueous 2'-deoxyguanosine solutions. The radiosensitizing capacity of a 9-nitro-5-deazflavin derivative was observed only in the N(2)O saturated aqueous solutions.

Electrolytically reduced 6- and 8-nitro-5-deazaflavin derivatives have been found to interact to react specifically with guanine base by means of cyclic voltammetry. Electrolytic reductions of 6- and 8-nitro-5-deazaflavin derivatives in the presence of the 2'-deoxyguanosine under anaerobic conditions resulted in prominent formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine.