Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 26, Pages 8972-8979Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600590
Keywords
dyes/pigments; energy transfer; fluorescent probes; imaging agents; proteins
Categories
Funding
- Hungarian Academy of Sciences [LP2013-55/2013]
- Hungarian Scientific Research Fund [NN-110214, NN-116265]
- FEBS Short-Term Fellowship
- [SPP1623]
- [SFB1129]
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The synthesis of a set of tetrazine-bearing fluorogenic dyes suitable for intracellular labeling of proteins in live cells is presented. The red excitability and emission properties ensure minimal autofluorescence, while throughbond energy-transfer-based fluorogenicity reduces nonspecific background fluorescence of unreacted dyes. The tetrazine motif efficiently quenches fluorescence of the phenoxazine core, which can be selectively turned on chemically upon bioorthogonal inverse-electron-demand Diels-Alder reaction with proteins modified genetically with strained trans-cyclooctenes.
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