Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (4): 500-508.DOI: 10.19894/j.issn.1000-0518.220308

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A Flavone-based “Off-On” Fluorescence Probe for Detecting Butyrylcholinesterase in Living Cell

Hong-Li YU1,2, Si-Yi ZHOU2, Chen HONG1(), Wen LUO2()   

  1. 1.Huaihe Hosipital,Henan University,Kaifeng 475000,China
    2.Key Laboratory of Natural Medicine and Immuno-Engineering,Henan University,Kaifeng 475004,China
  • Received:2022-09-20 Accepted:2023-02-14 Published:2023-04-01 Online:2023-04-17
  • Contact: Chen HONG,Wen LUO
  • About
  • Supported by:
    the Science and Technology Planning Project of Henan Province(212102311030)


An “off-on” fluorescence probe (4a) based on NN-(dimethylamino)naphthalenyl flavone (3) is designed and synthesized for detection of butyrylcholinesterase (BChE) by using resorcinol as starting materials. The structure of the probe is identified by nuclear magnetic resonance spectroscopy (NMR) and high resolution mass spectrometry (HRMS). The results show that probe 4a could react rapidly and specifically with BChE, and its fluorescence intensity increases obviously at 574 nm in PBS of pH 8.0. Meanwhile, the color change of the solution can be seen by naked eyes. The response mechanism is explored through high performance liquid chromatography (HPLC) and HRMS. The results reveal that BChE catalyzes the cleavage of the ester bond, and strongly fluorescent flavone 3 is released. In addition, probe 4a could be used for fluorescence imaging of BChE in living human hepatocellular carcinoma (HepG2) cells.

Key words: Flavone, Butyrylcholinesterase, Fluorescence probe

CLC Number: