New Red-Emitting Tetrazine-Phenoxazine Fluorogenic Labels for Live-Cell Intracellular Bioorthogonal Labeling Schemes

Knorr, Gergely and Kozma, Eszter and Herner, András and Lemke, E. A. and Kele, Péter (2016) New Red-Emitting Tetrazine-Phenoxazine Fluorogenic Labels for Live-Cell Intracellular Bioorthogonal Labeling Schemes. CHEMISTRY-A EUROPEAN JOURNAL, 22 (26). pp. 8972-8979. ISSN 0947-6539

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Official URL: https://doi.org/10.1002/chem.201600590

Abstract

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. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Item Type:	Article
Uncontrolled Keywords:	PROTEINS; FLUORESCENCE; biosynthesis; fluorescent probes; imaging agents; Energy transfer; Imaging agent; autofluorescence; Labeling scheme; Emission properties; Inverse-electron demand diels-alder reactions; Bond energies; Dyes/pigments;
Subjects:	Q Science / természettudomány > QD Chemistry / kémia
SWORD Depositor:	MTMT SWORD
Depositing User:	MTMT SWORD
Date Deposited:	17 Jan 2019 13:11
Last Modified:	17 Jan 2019 13:11
URI:	http://real.mtak.hu/id/eprint/90123

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