Jump to main content
Jump to site search

Issue 9, 2016
Previous Article Next Article

Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions

Author affiliations

Abstract

A nucleoside bearing a solvatochromic push–pull fluorene fluorophore (dCFL) was designed and synthesized by the Sonogashira coupling of alkyne-linked fluorene 8 with 5-iodo-2′-deoxycytidine. The fluorene building block 8 and labeled nucleoside dCFL exerted bright fluorescence with significant solvatochromic effect providing emission maxima ranging from 421 to 544 nm and high quantum yields even in highly polar solvents, including water. The solvatochromism of 8 was studied by DFT and ADC(2) calculations to show that, depending on the polarity of the solvent, emission either from the planar or the twisted conformation of the excited state can occur. The nucleoside was converted to its triphosphate variant dCFLTP which was found to be a good substrate for DNA polymerases suitable for the enzymatic synthesis of oligonucleotide or DNA probes by primer extension or PCR. The fluorene-linked DNA can be used as fluorescent probes for DNA–protein (p53) or DNA–lipid interactions, exerting significant color changes visible even to the naked eye. They also appear to be suitable for time-dependent fluorescence shift studies on DNA, yielding information on DNA hydration and dynamics.

Graphical abstract: Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Jun 2016, accepted on 20 Jun 2016 and first published on 21 Jun 2016


Article type: Edge Article
DOI: 10.1039/C6SC02548J
Citation: Chem. Sci., 2016,7, 5775-5785
  • Open access: Creative Commons BY license
  •   Request permissions

    Solvatochromic fluorene-linked nucleoside and DNA as color-changing fluorescent probes for sensing interactions

    D. Dziuba, P. Pospíšil, J. Matyašovský, J. Brynda, D. Nachtigallová, L. Rulíšek, R. Pohl, M. Hof and M. Hocek, Chem. Sci., 2016, 7, 5775
    DOI: 10.1039/C6SC02548J

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements