An Expeditious Approach towards the Synthesis and Application of Water-Soluble and Photostable Fluorogenic Chromones for DNA Detection

An Expeditious Approach towards the Synthesis and Application of Water-Soluble and Photostable Fluorogenic Chromones for DNA Detection

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...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-03, Vol.27 (7), p.2267
Main Authors: Vincent, Steve, Mallick, Suman, Barnoin, Guillaume, Le, Hoang-Ngoan, Michel, Benoît Y, Burger, Alain
Format: Article
Language:eng
Subjects:
Chemical Sciences
Chemistry
Chromones
Chromophores
Deoxyribonucleic acid
DNA
DNA methylation
DNA Probes
Dyes
Fluorescent Dyes
fluorogenic sensing
Hybridization
Labeling
multistep synthesis
Oligonucleotides
Organic chemistry
Organic solvents
post-synthetic ODN labeling
Water
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Summary: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 ( ). 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 in water, conjugate readily with oligonucleotides, and furthermore demonstrate sensitivity to hydration, thus paving the way for a high-performance fluorogenic DNA hybridization probe.
ISSN:1420-3049
1420-3049