BODIPY-Based Fluorescent Probes for Selective Visualization of Endogenous Hypochlorous Acid in Living Cells via Triazolopyridine Formation.

Autor:	Hiranmartsuwan P; National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani 12120, Thailand., Wangngae S; School of Chemistry, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima 30000, Thailand., Nootem J; National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani 12120, Thailand., Kamkaew A; School of Chemistry, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima 30000, Thailand., Daengngern R; Integrated Applied Chemistry Research Unit, King Mongkut's Institute of Technology Ladkrabang, School of Science, Bangkok 10520, Thailand., Wattanathana W; Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Ladyao, Chatuchak, Bangkok 10900, Thailand., Chansaenpak K; National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani 12120, Thailand.
Jazyk:	angličtina
Zdroj:	Biosensors [Biosensors (Basel)] 2022 Oct 25; Vol. 12 (11). Date of Electronic Publication: 2022 Oct 25.
DOI:	10.3390/bios12110923
Abstrakt:	In this work, the two pyridylhydrazone-tethered BODIPY compounds ( 2 and 3 ) were synthesized. These compounds aimed to detect hypochlorous acid (HOCl) species via cyclic triazolopyridine formation. The open forms and the resulting cyclic forms of BODIPYs ( 2 , 3 , 4 , and 5 ) were fully characterized by nuclear magnetic resonance, mass spectrometry, infrared spectroscopy, and single-crystal X-ray diffraction. These two probes can selectively detect HOCl through a fluorescence turn-on mechanism with the limit of detections of 0.21 µM and 0.77 µM for compounds 2 and 3 , respectively. This fluorescence enhancement phenomenon could be the effect from C = N isomerization inhibition due to HOCl-triggered triazolopyridine formation. In cell imaging experiments, these compounds showed excellent biocompatibility toward RAW 264.7 murine live macrophage cells and greatly visualized endogenous HOCl in living cells stimulated with lipopolysaccharide. Competing Interests: The authors declare no conflict of interest.
Databáze:	MEDLINE
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