Premium
An Extended Approach for the Development of Fluorogenic trans ‐Cyclooctene–Tetrazine Cycloadditions
Author(s) -
Siegl Sebastian J.,
Galeta Juraj,
Dzijak Rastislav,
Vázquez Arcadio,
Del RíoVillanueva Miguel,
Dračínský Martin,
Vrabel Milan
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800711
Subject(s) - tetrazine , cycloaddition , bioorthogonal chemistry , bioconjugation , cyclooctene , fluorescence , chemistry , combinatorial chemistry , organic chemistry , catalysis , click chemistry , physics , quantum mechanics
Inverse‐electron‐demand Diels–Alder (iEDDA) cycloaddition between 1,2,4,5‐tetrazines and strained dienophiles belongs among the most popular bioconjugation reactions. In addition to its fast kinetics, this cycloaddition can be tailored to produce fluorescent products from non‐fluorescent starting materials. Here we show that even the reaction intermediates formed in iEDDA cycloaddition can lead to the formation of new types of fluorophores. The influence of various substituents on their photophysical properties and the generality of the approach with use of various trans ‐cyclooctene derivatives were studied. Model bioimaging experiments demonstrate the application potential of fluorogenic iEDDA cycloaddition.