A General Strategy to Design Highly Fluorogenic Far-Red and Near-Infrared Tetrazine Bioorthogonal Probes

Wuyu Mao, Jie Tang, Liqun Dai, Xinyu He, Jie Li, Larry Cai, Ping Liao, Ruotian Jiang, Jingwei Zhou, Haoxing Wu

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46 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2393-2397
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number5
DOIs
Publication statusPublished - 1 Feb 2021
Externally publishedYes

Keywords

  • bioorthogonal chemistry
  • fluorophores
  • imaging
  • near-infrared probes
  • tetrazine

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