A Universal Nucleoside
with Strong Two-Band Switchable
Fluorescence and Sensitivity to the Environment for Investigating
DNA Interactions
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Abstract
With the aim of developing a new tool to investigate
DNA interactions,
a nucleoside analogue incorporating a 3-hydroxychromone (3HC) fluorophore
as a nucleobase mimic was synthesized and incorporated into oligonucleotide
chains. In comparison with existing fluorescent nucleoside analogues,
this dye features exceptional environmental sensitivity switching
between two well-resolved fluorescence bands. In labeled DNA, this
nucleoside analogue does not alter the duplex conformation and exhibits
a high fluorescence quantum yield. This probe is up to 50-fold brighter
than 2-aminopurine, the fluorescent nucleoside standard. Moreover,
the dual emission is highly sensitive to the polarity of the environment;
thus, a strong shielding effect of the flanking bases from water was
observed. With this nucleoside, the effect of a viral chaperone protein
on DNA base stacking was site-selectively monitored