Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs

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 (Δλmaxem=91nm),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.

Chemical structures of aromatic fluorophore substituted purine nucleosides.Figure optionsDownload as PowerPoint slide