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Rational Design of a Solvatochromic Fluorescent Uracil Analogue with a Dual‐Band Ratiometric Response Based on 3‐Hydroxychromone
Author(s) -
Dziuba Dmytro,
Karpenko Iuliia A.,
Barthes Nicolas P. F.,
Michel Benoît Y.,
Klymchenko Andrey S.,
Benhida Rachid,
Demchenko Alexander P.,
Mély Yves,
Burger Alain
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303399
Subject(s) - solvatochromism , fluorophore , fluorescence , bathochromic shift , photochemistry , chemistry , uracil , rational design , absorption (acoustics) , solvent , materials science , dna , organic chemistry , nanotechnology , optics , biochemistry , physics , composite material
Fluorescent nucleoside analogues with strong and informative responses to their local environment are in urgent need for DNA research. In this work, the design, synthesis and investigation of a new solvatochromic ratiometric fluorophore compiled from 3‐hydroxychromones (3HCs) and uracil fragments are reported. 3HC dyes are a class of multi‐parametric, environment‐sensitive fluorophores providing a ratiometric response due to the presence of two well‐resolved bands in their emission spectra. The synthesized conjugate demonstrates not only the preservation but also the improvement of these properties. The absorption and fluorescence spectra are shifted to longer wavelengths together with an increase of brightness. Moreover, the two fluorescence bands are better resolved and provide ratiometric responses across a broader range of solvent polarities. To understand the photophysical properties of this new fluorophore, a series of model compounds were synthesized and comparatively investigated. The obtained data indicate that uracil and 3HC fragments of this derivative are coupled into an electronic conjugated system, which on excitation attains strong charge‐transfer character. The developed fluorophore is a prospective label for nucleic acids. Abstract in Ukrainian:.