A “reactive” turn-on fluorescence probe for hypochlorous acid and its bioimaging application

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 206; pp. 190 - 196
• Main Authors: Gao, Yunling, Pan, Yong, Chi, Yu, He, Yuanyuan, Chen, Haiyan, Nemykin, Victor N.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 05.01.2019
• Subjects: Aldoxime; Animals; aza-BODIPY; Boron Compounds - chemistry; Fluorescent Dyes - chemistry; Hypochlorous Acid - analysis; Mice; Microscopy, Fluorescence - methods; Oxidation-Reduction; Oximes - chemistry; RAW 264.7 Cells; Red-emission; Spectrometry, Fluorescence; Turn-on probe; Turn-on probe; Aldoxime; aza-BODIPY; Red-emission
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2018.07.090

An aza-BODIPY-CNOH probe attached aldoxime group demonstrated the specific detection for hypochlorous acid by the turn-on red emission signal. NMR and HRMS experiments confirmed that the fluorescence originated from the oxidation degradation of the non-fluorescence, aldoxime-based aza-BODIPY-CNOH probe into the red-fluorescence, nitrile oxide-based aza-BODIPY compound aza-BODIPY-CNO. The aza-BODIPY-CNOH probe showed good biocompatibility and was low toxic to living cells as shown from MTT experiments. Living RAW264.7 cells imaging indicated the aza-BODIPY-CNOH probe had good permeability and either exogenous or endogenous HClO caused the intracellular bright-red fluorescence, showing its potential hypochlorous acid-specific sensing ability in biological systems. [Display omitted] •A turn-on aza-BODIPY-CNOH probe has been synthesized and characterized.•The aza-BODIPY-CNOH probe showed specific fluorescence recognition for HClO.•The turn-on fluorescence may originate from the aza-BODIPY nitrile oxide product oxidized by HClO.•The aza-BODIPY-CNOH probe can detect exogenous and endogenous HClO in living cells.