Synthesis of a Near-Infrared Fluorescent Probe for Imaging Catecholamines via a Tandem Nucleophilic Aromatic Substitution

A near-infrared (NIR) fluorescent probe NS667 was developed using a novel synthetic strategy by integrating an electron-rich 1,2,3,4-tetrahydroquinoxaline (THQ) into the scaffold from NS510, which binds to catecholamines with high affinity. The fluorophore core was constructed with a tandem nucleoph...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (51), p.9103-9107
Main Authors: Zhang, Le, Liu, Xin A., Gillis, Kevin D., Glass, Timothy E.
Format: Article
Language:English
Subjects:
Catecholamines
Fluorescence
Fluorescent Dyes
Norepinephrine
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Summary:A near-infrared (NIR) fluorescent probe NS667 was developed using a novel synthetic strategy by integrating an electron-rich 1,2,3,4-tetrahydroquinoxaline (THQ) into the scaffold from NS510, which binds to catecholamines with high affinity. The fluorophore core was constructed with a tandem nucleophilic aromatic substitution. Upon binding to catecholamines, the fluorescence of this probe shifted, with the emission in the NIR region. Live cell imaging results demonstrate that NS667 can effectively image norepinephrine in chromaffin cells with shifted fluorescence, which highlights the potential of the probe for neuroimaging in tissues.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03343