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A General Strategy to Design Highly Fluorogenic Far‐Red and Near‐Infrared Tetrazine Bioorthogonal Probes
Author(s) -
Mao Wuyu,
Tang Jie,
Dai Liqun,
He Xinyu,
Li Jie,
Cai Larry,
Liao Ping,
Jiang Ruotian,
Zhou Jingwei,
Wu Haoxing
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011544
Subject(s) - bioorthogonal chemistry , tetrazine , fluorophore , fluorescence , conjugate , chemistry , excitation wavelength , nanotechnology , infrared , photochemistry , materials science , combinatorial chemistry , click chemistry , optics , organic chemistry , physics , mathematical analysis , mathematics
Highly fluorogenic tetrazine bioorthogonal probes emitting at near‐infrared wavelengths are in strong demand for biomedical imaging applications. Herein, we have developed a strategy for forming a palette of novel Huaxi‐Fluor probes in situ, whose fluorescence increases hundreds of times upon forming the bioorthogonal reaction product, pyridazine. The resulting probes show large Stokes shifts and high quantum yields. Manipulating the conjugate length and pull–push strength in the fluorophore skeleton allows the emission wavelength to be fine‐tuned from 556 to 728 nm. The highly photo‐stable and biocompatible probes are suitable for visualizing organelles in live cells without a washing step and for imaging of tumors in live small animals to depths of 500 μm by two‐photon excitation.