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An Expeditious Approach towards the Synthesis and Application of Water-Soluble and Photostable Fluorogenic Chromones for DNA Detection
Authors:Steve Vincent,Suman Mallick,Guillaume Barnoin,Hoang-Ngoan Le,Benoî  t Y. Michel,Alain Burger
Affiliation:Institut de Chimie de Nice, CNRS UMR 7272, Université Côte d’Azur, Parc Valrose, CEDEX 2, 06108 Nice, France; (S.V.); (S.M.); (G.B.); (H.-N.L.)
Abstract:
The intensive research for hybridization probes based on organic molecules with fluorogenic properties is currently attracting particular attention due to their potential to efficiently recognize different DNA conformations and the local environment. However, most established organic chromophores do not meet the requirements of this task, as they do not exhibit good brightness in aqueous buffer media, develop aggregation and/or are not easily conjugated to oligodeoxynucleotides (ODNs) while keeping their photophysics intact. Herein, an important modification strategy was employed for a well-known fluorophore, 2-(4-(diethylamino)phenyl)-3-hydroxychromone (dEAF). Although this push–pull dye absorbs intensively in the visible range and shows emission with large Stokes shifts in all organic solvents, it is strongly quenched in water. This Achilles’ heel prompted us to implement a new strategy to obtain a series of dyes that retain all the photophysical features of dEAF in water, conjugate readily with oligonucleotides, and furthermore demonstrate sensitivity to hydration, thus paving the way for a high-performance fluorogenic DNA hybridization probe.
Keywords:fluorescent dyes   chromones   post-synthetic ODN labeling   hybridization   fluorogenic sensing   multistep synthesis
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