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Issue 42, 2015
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Development of environmentally sensitive fluorescent and dual emissive deoxyuridine analogues

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Abstract

Ratiometric and environment-sensitive fluorescent dyes present attractive advantages for sensing interactions in DNA research. Here, we report the rational design, synthesis, and photophysical characterization of 2-thienyl-, 2-furyl- and 2-phenyl-3-hydroxychromones bonded to the C-5 position of deoxyuridine. Since these two-color nucleosides were designed for incorporation into ODNs, we also investigated the sensitivity of the ratiometric response to hydration by using acetonitrile/water mixtures and neat solvents. The synthesized 2-thienyl and 2-furyl conjugates were found to exhibit more red-shifted absorption (by 31–36 nm) and emission (by 77–81 nm of the N* band), two-fold increased molar absorption coefficients, and dramatically enhanced (by 3–4.5 times) fluorescence quantum yields. Demonstrating a manifold increase in brightness, they preserve the ability of exquisite ratiometric responses to solvent polarity and hydration. This makes the new fluorescent nucleoside analogues highly relevant for subsequent labeling of the major groove in nucleic acids and sensing their interactions.

Graphical abstract: Development of environmentally sensitive fluorescent and dual emissive deoxyuridine analogues

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Publication details

The article was received on 11 Feb 2015, accepted on 01 Apr 2015 and first published on 01 Apr 2015


Article type: Paper
DOI: 10.1039/C5RA02709H
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 33536-33545
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    Development of environmentally sensitive fluorescent and dual emissive deoxyuridine analogues

    N. P. F. Barthes, I. A. Karpenko, D. Dziuba, M. Spadafora, J. Auffret, A. P. Demchenko, Y. Mély, R. Benhida, B. Y. Michel and A. Burger, RSC Adv., 2015, 5, 33536
    DOI: 10.1039/C5RA02709H

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