An Extended Approach for the Development of Fluorogenic trans-Cyclooctene-Tetrazine Cycloadditions
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
30561884
PubMed Central
PMC6471176
DOI
10.1002/cbic.201800711
Knihovny.cz E-resources
- Keywords
- bioorthogonal chemistry, click chemistry, cycloaddition, heterocycles, tetrazines,
- MeSH
- Cycloaddition Reaction MeSH
- Cyclooctanes chemistry MeSH
- Fluorescent Dyes chemical synthesis chemistry MeSH
- Microscopy, Fluorescence methods MeSH
- HeLa Cells MeSH
- Heterocyclic Compounds, 2-Ring chemical synthesis chemistry MeSH
- Heterocyclic Compounds, 1-Ring chemistry MeSH
- Microscopy, Confocal methods MeSH
- Humans MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Cyclooctanes MeSH
- Fluorescent Dyes MeSH
- Heterocyclic Compounds, 2-Ring MeSH
- Heterocyclic Compounds, 1-Ring MeSH
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.
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