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New Red‐Emitting Tetrazine‐Phenoxazine Fluorogenic Labels for Live‐Cell Intracellular Bioorthogonal Labeling Schemes
Author(s) -
Knorr Gergely,
Kozma Eszter,
Herner András,
Lemke Edward A.,
Kele Péter
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600590
Subject(s) - tetrazine , bioorthogonal chemistry , phenoxazine , fluorescence , chemistry , combinatorial chemistry , intracellular , förster resonance energy transfer , biochemistry , biophysics , click chemistry , biology , organic chemistry , physics , pharmacology , phenothiazine , quantum mechanics
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 through‐bond 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.