title: Rational design of a solvatochromic fluorescent uracil analogue with a dual-band ratiometric response based on 3-hydroxychromone.
abstract: 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: .
authors.affiliation: Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, CNRS, Parc Valrose, 06108 Nice cedex 2 (France); Present address: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, CZ-16610, Prague 6 (Czech Republic).
authors.forename: Dmytro
authors.initials: D
authors.lastname: Dziuba
authors.forename: Iuliia A
authors.initials: IA
authors.lastname: Karpenko
authors.forename: Nicolas P F
authors.initials: NP
authors.lastname: Barthes
authors.forename: Benoît Y
authors.initials: BY
authors.lastname: Michel
authors.forename: Andrey S
authors.initials: AS
authors.lastname: Klymchenko
authors.forename: Rachid
authors.initials: R
authors.lastname: Benhida
authors.forename: Alexander P
authors.initials: AP
authors.lastname: Demchenko
authors.forename: Yves
authors.initials: Y
authors.lastname: Mély
authors.forename: Alain
authors.initials: A
authors.lastname: Burger
mesh_terms: D002867:Chromones / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D014498:Uracil / Q000031:analogs & derivatives*
chemical_list: C479534:3-hydroxychromone; D002867:Chromones; D005456:Fluorescent Dyes; D014498:Uracil
keywords: charge transfer; fluorescent probes; nucleobases; solvatochromism; time-resolved spectroscopy