A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging
| Autor: | Martin Dračínský, Juraj Galeta, Rastislav Dzijak, Milan Vrabel, Jan Obořil |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Fluorescence-lifetime imaging microscopy
tetrazines 010402 general chemistry 01 natural sciences Fluorescent Probes | Hot Paper Catalysis live cell bioimaging chemistry.chemical_compound Tetrazine Heterocyclic Compounds Cell Line Tumor Humans Fluorescent Dyes Microscopy Confocal coumarins Full Paper 010405 organic chemistry Optical Imaging Organic Chemistry General Chemistry Full Papers Coumarin Fluorescence Combinatorial chemistry 0104 chemical sciences chemistry Reagent click chemistry Click chemistry fluorescence Bioorthogonal chemistry Light Up |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) Chemistry – A European Journal |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | 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 with trans‐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. Light on! A series of seventeen coumarin–tetrazine probes that produce in reaction with trans‐cyclooctene and bicyclononyne dienophile bright fluorophores were synthesized and evaluated in different bioimaging applications. These probes show excellent turn‐on properties and can be used for fast and selective bioorthogonal fluorescence labeling in live cells. |
| Databáze: | OpenAIRE |
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