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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00463825" target="_blank" >RIV/61388963:_____/16:00463825 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388955:_____/16:00463825 RIV/00216208:11310/16:10328274

Výsledek na webu

<a href="http://pubs.rsc.org/en/content/articlepdf/2016/sc/c6sc02548j" target="_blank" >http://pubs.rsc.org/en/content/articlepdf/2016/sc/c6sc02548j</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c6sc02548j" target="_blank" >10.1039/c6sc02548j</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

A nucleoside bearing a solvatochromic push-pull fluorene fluorophore (dC(FL)) 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 dC(FL) 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 dC(FL)TP 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.

Název v anglickém jazyce

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

Popis výsledku anglicky

A nucleoside bearing a solvatochromic push-pull fluorene fluorophore (dC(FL)) 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 dC(FL) 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 dC(FL)TP 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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemical Science

ISSN

2041-6520

e-ISSN

—

Svazek periodika

7

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

5775-5785

Kód UT WoS článku

000382488500021

EID výsledku v databázi Scopus

2-s2.0-84983387424