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

Content Provider	Royal Society of Chemistry (RSC)
Author	Dziuba, Dmytro Pospíšil, Petr Hof, Martin Brynda, Jiří Rulíšek, Lubomír Nachtigallová, Dana Matyašovský, Ján Pohl, Radek Hocek, Michal
Copyright Year	2016
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.
Starting Page	5775
Ending Page	5785
Page Count	11
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	9
Journal	Chemical Science
DOI	10.1039/c6sc02548j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Fluorene Solvatochromism Fluorescence P53 Sonogashira coupling Polymerase chain reaction Quantum Polyphosphate Fluorophore Deoxycytidine DNA Nucleoside Oligonucleotide Push\u2013pull train Solvent Protein structure
Content Type	Text
Resource Type	Article
Subject	Chemistry

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