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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA19-13811S" target="_blank" >GA19-13811S: Construction of synthetic scaffolds enabling subcellular organelle-specific release chemistry</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2020

Confidentiality

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

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

—

Volume of the periodical

26

Issue of the periodical within the volume

44

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

9945-9953

UT code for WoS article

000548211000001

EID of the result in the Scopus database

2-s2.0-85087924074