Sequence specific recognition of ssDNA by fluorophore 3-hydroxyflavone

A fully water soluble 3-hydroxyflavone (3HF) derivative, N-(3-hydroxy-4′-flavonyl)-N,N,N-trimethylammonium sulfate (3HFNMe3) was synthesized. Investigation of its emissions at varying wavelengths revealed that it had three emission bands of normal (N⁎), anionic (A⁎) and tautomeric (T⁎), in ultrapure water. Recognition of single-stranded ten ssDNA chains, having different nucleotide sequences was studied, using the ratiometric change of the intensities of the two bands (A⁎/T⁎), depending upon the varying environment of the 3HFNMe3 with different ssDNA chains. Addition of the ssDNA chains to the 3HFNMe3 solution caused gradual quenching of the A⁎ band and had almost no effect on the T⁎ band. As the ratios of the two bands (A⁎/T⁎) vs increasing amount of the ssDNAs generated characteristic curves for each ssDNA chain, it became possible to identify the chains with their characteristic curves. [Display omitted] •A new fully water soluble 3-hydroxyflavone derivative, having neutral (N⁎), anionic (A⁎) and tautomeric (T⁎) emissions.•A new sensing approach with anionic (A⁎) and tautomeric (T⁎) emissions.•Differentiating ssDNAs, having different nucleotide chains, using emission ratios of A⁎/T⁎.