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A General Strategy to Design Highly Fluorogenic Far-Red and Near-Infrared Tetrazine Bioorthogonal Probes. 2021

Wuyu Mao, and Jie Tang, and Liqun Dai, and Xinyu He, and Jie Li, and Larry Cai, and Ping Liao, and Ruotian Jiang, and Jingwei Zhou, and Haoxing Wu
Huaxi MR Research Center, Department of Nuclear Medicine, Frontiers Science Center for Disease-related Molecular Network, National Clinical Research Center for Geriatrics, West China Hospital, Sichuan University, Chengdu, 610041, China.

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.

UI MeSH Term Description Entries
D006573 Heterocyclic Compounds, 1-Ring Organic compounds that contain a ring structure made up of carbon and one or more additional elements such as nitrogen and oxygen. Heterocyclic Cpds, 1-Ring,1-Ring Heterocyclic Compounds,1-Ring Heterocyclic Cpds,Heterocyclic Compounds, 1 Ring,Heterocyclic Cpds, 1 Ring
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D061848 Optical Imaging The use of light interaction (scattering, absorption, and fluorescence) with biological tissue to obtain morphologically based information. It includes measuring inherent tissue optical properties such as scattering, absorption, and autofluorescence; or optical properties of exogenous targeted fluorescent molecular probes such as those used in optical MOLECULAR IMAGING, or nontargeted optical CONTRAST AGENTS. Fundus Autofluorescence Imaging,Autofluorescence Imaging,Fluorescence Imaging,Autofluorescence Imaging, Fundus,Fundus Autofluorescence Imagings,Imaging, Autofluorescence,Imaging, Fluorescence,Imaging, Fundus Autofluorescence,Imaging, Optical
D019265 Spectroscopy, Near-Infrared A noninvasive technique that uses the differential absorption properties of hemoglobin and myoglobin to evaluate tissue oxygenation and indirectly can measure regional hemodynamics and blood flow. Near-infrared light (NIR) can propagate through tissues and at particular wavelengths is differentially absorbed by oxygenated vs. deoxygenated forms of hemoglobin and myoglobin. Illumination of intact tissue with NIR allows qualitative assessment of changes in the tissue concentration of these molecules. The analysis is also used to determine body composition. NIR Spectroscopy,Spectrometry, Near-Infrared,NIR Spectroscopies,Near-Infrared Spectrometries,Near-Infrared Spectrometry,Near-Infrared Spectroscopies,Near-Infrared Spectroscopy,Spectrometries, Near-Infrared,Spectrometry, Near Infrared,Spectroscopies, NIR,Spectroscopies, Near-Infrared,Spectroscopy, NIR,Spectroscopy, Near Infrared

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