A Systematic Study of Coumarin-Tetrazine Light-Up Probes for Bioorthogonal Fluorescence Imaging

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00531412" target="_blank" >RIV/61388963:_____/20:00531412 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1002/chem.202001290" target="_blank" >https://doi.org/10.1002/chem.202001290</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.202001290" target="_blank" >10.1002/chem.202001290</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A Systematic Study of Coumarin-Tetrazine Light-Up Probes for Bioorthogonal Fluorescence Imaging

Popis výsledku v původním jazyce

Fluorescent probes that light-up upon reaction with complementary bioorthogonal reagents are superior tools for no-wash fluorogenic bioimaging applications. In this work, a thorough study is presented on a set of seventeen structurally diverse coumarin-tetrazine probes that produce fluorescent dyes with exceptional turn-on ratios when reacted withtrans-cyclooctene (TCO) and bicyclononyne (BCN) dienophiles. In general, formation of the fully aromatic pyridazine-containing dyes resulting from the reaction with BCN was found superior in terms of fluorogenicity. However, evaluation of the probes in cellular imaging experiments revealed that other factors, such as reaction kinetics and good cell permeability, prevail over the fluorescence turn-on properties. The best compound identified in this study showed excellent performance in live cell-labeling experiments and enabled no-wash fluorogenic imaging on a timescale of seconds.

Název v anglickém jazyce

A Systematic Study of Coumarin-Tetrazine Light-Up Probes for Bioorthogonal Fluorescence Imaging

Popis výsledku anglicky

Fluorescent probes that light-up upon reaction with complementary bioorthogonal reagents are superior tools for no-wash fluorogenic bioimaging applications. In this work, a thorough study is presented on a set of seventeen structurally diverse coumarin-tetrazine probes that produce fluorescent dyes with exceptional turn-on ratios when reacted withtrans-cyclooctene (TCO) and bicyclononyne (BCN) dienophiles. In general, formation of the fully aromatic pyridazine-containing dyes resulting from the reaction with BCN was found superior in terms of fluorogenicity. However, evaluation of the probes in cellular imaging experiments revealed that other factors, such as reaction kinetics and good cell permeability, prevail over the fluorescence turn-on properties. The best compound identified in this study showed excellent performance in live cell-labeling experiments and enabled no-wash fluorogenic imaging on a timescale of seconds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA19-13811S" target="_blank" >GA19-13811S: Konstrukce syntetických látek umožňujících uvolňování malých molekul v specifických buněčných organelách</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

—

Svazek periodika

26

Číslo periodika v rámci svazku

44

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

9945-9953

Kód UT WoS článku

000548211000001

EID výsledku v databázi Scopus

2-s2.0-85087924074