An Extended Approach for the Development of Fluorogenic trans-Cyclooctene–Tetrazine Cycloadditions |
| |
| Authors: | Sebastian J Siegl Dr Juraj Galeta Dr Rastislav Dzijak Dr Arcadio Vázquez Miguel Del?Río-Villanueva Dr Martin Dra?ínský Dr Milan Vrabel |
| |
| Affiliation: | Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague, Czech Republic |
| |
| Abstract: | 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. |
| |
| Keywords: | bioorthogonal chemistry click chemistry cycloaddition heterocycles tetrazines |
|
|
