3-Hydroxybenzo[g]chromones: Fluorophores with red-shifted absorbance and highly sensitive to polarity emission

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00490346" target="_blank" >RIV/61388963:_____/18:00490346 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.snb.2018.03.058" target="_blank" >http://dx.doi.org/10.1016/j.snb.2018.03.058</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.snb.2018.03.058" target="_blank" >10.1016/j.snb.2018.03.058</a>

Jazyk výsledku

angličtina

Název v původním jazyce

3-Hydroxybenzo[g]chromones: Fluorophores with red-shifted absorbance and highly sensitive to polarity emission

Popis výsledku v původním jazyce

Solvatochromic probes based on 3-hydroxychromones are often used to study interactions of biomolecules in spectroscopy and microscopy setups. However, due to their UV or violet absorbance these probes have limited application for live-cell imaging. In this work, we developed a series of benzochromones with red-shifted absorbance by introducing a fused benzene ring and substituents with extended pi-electron conjugated system in the position 2. Developed 3-hydroxybenzo[g]chromones demonstrated improved sensitivity to the polarity of local environment when compared to other known solvatochromic dyes absorbing in the same spectral region. We tuned the fluorescence properties of benzochromones by varying the substituents in the position 2. Thus 2-(6'-dimethylaminobenzofury1)-3-hydroxybenzochromone (BFBC) showed two emission bands in hydrophobic environments due to the ESIPT reaction and providing a ratiometric response highly sensitive to the polarity of the dye environment. We found that BFBC is a suitable dye for fluorescence microscopy and in contrast to other known 3-hydroxychromones, BFBC possesses a convenient excitation with a common 488 nm argon laser. Together with high solvatochromism and ratiometric response it makes BFBC a prospective fluorophore for probe development and application in biological research.

Název v anglickém jazyce

3-Hydroxybenzo[g]chromones: Fluorophores with red-shifted absorbance and highly sensitive to polarity emission

Popis výsledku anglicky

Solvatochromic probes based on 3-hydroxychromones are often used to study interactions of biomolecules in spectroscopy and microscopy setups. However, due to their UV or violet absorbance these probes have limited application for live-cell imaging. In this work, we developed a series of benzochromones with red-shifted absorbance by introducing a fused benzene ring and substituents with extended pi-electron conjugated system in the position 2. Developed 3-hydroxybenzo[g]chromones demonstrated improved sensitivity to the polarity of local environment when compared to other known solvatochromic dyes absorbing in the same spectral region. We tuned the fluorescence properties of benzochromones by varying the substituents in the position 2. Thus 2-(6'-dimethylaminobenzofury1)-3-hydroxybenzochromone (BFBC) showed two emission bands in hydrophobic environments due to the ESIPT reaction and providing a ratiometric response highly sensitive to the polarity of the dye environment. We found that BFBC is a suitable dye for fluorescence microscopy and in contrast to other known 3-hydroxychromones, BFBC possesses a convenient excitation with a common 488 nm argon laser. Together with high solvatochromism and ratiometric response it makes BFBC a prospective fluorophore for probe development and application in biological research.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

Sensors and Actuators B - Chemical

ISSN

0925-4005

e-ISSN

—

Svazek periodika

265

Číslo periodika v rámci svazku

Jul 15

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

8

Strana od-do

691-698

Kód UT WoS článku

000430232500083

EID výsledku v databázi Scopus

2-s2.0-85044129528