Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 22, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202117386
Keywords
Bioorthogonal Chemistry; Fluorogenicity; Near-Infrared Fluorophores; Photoinduced Electron Transfer; Tetrazine
Categories
Funding
- National Natural Science Foundation of China [21977075, 21807075]
- Fundamental Research Funds for the Central Universities
- China Postdoctoral Science Foundation [2018M643464]
- 1.3.5 Project for Disciplines of Excellence, West China Hospital, Sichuan University
- Post-Doctoral Research Fund at West China Hospital, Sichuan University [2018HXBH081]
- A*STAR under its Advanced Manufacturing and Engineering Program [A2083c0051]
- Ministry of Education, Singapore [MOE-MOET2EP10120-0007]
- Singapore University of Technology and Design [SUTD-ZJU (VP)201905]
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In this study, a generalizable molecular design strategy was reported to construct ultra-fluorogenic dyes by simple substitution at the meso-positions of various far-red and NIR fluorophores. The probes showed significant fluorescence turn-on ratios in the range of 586-806 nm. These results will greatly expand the applications of bioorthogonal chemistry in NIR bioimaging and biosensing.
Bioorthogonal fluorogenic dyes are indispensable tools in wash-free bioimaging of specific biological targets. However, the fluorogenicity of existing tetrazine-based bioorthogonal probes deteriorates as the emission wavelength shifts towards the NIR window, greatly limiting their applications in live cells and tissues. Herein, we report a generalizable molecular design strategy to construct ultra-fluorogenic dyes via a simple substitution at the meso-positions of various far-red and NIR fluorophores. Our probes demonstrate significant fluorescence turn-on ratios (10(2)-10(3)-fold) in the range 586-806 nm. These results will greatly expand the applications of bioorthogonal chemistry in NIR bioimaging and biosensing.
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