Citation: CAO Xiao-Yan, LU Hong-Zhao, ZHANG Qiang, REN Chuan-Qing, LIU Jian-Li. Design and Synthesis of Flavone-based Fluorescent Probe for Cysteine Detection and Its Application in Living Cells Imaging[J]. Chinese Journal of Analytical Chemistry, ;2020, 48(8): 1033-1040. doi: 10.19756/j.issn.0253-3820.191686 shu

Design and Synthesis of Flavone-based Fluorescent Probe for Cysteine Detection and Its Application in Living Cells Imaging

1.
Key Laboratory of Catalysis in Shaanxi Province, Shaanxi University of Technology, Hanzhong 723000, China;
2.
School of Biological Science and Engineering, Shaanxi University of Technology, Hanzhong 723000, China;
3.
Biomedicine Key Laboratory of Shaanxi Province, College of Life Science, Northwest University, Xi'an 710069, China

Received Date: 21 November 2019
Revised Date: 15 May 2020

Fund Project: This work was supported by the National Natural Science Foundation of China (No.21502109) and the Funds of Research Programs of Shaanxi University of Technology (No. SLG1811).

A highly selective and sensitive fluorescent probe 2-(2-furyl)-7-methoxychromone-3-acrylate (HFAC) was designed and synthesized with paeonol and furfural as raw material, 3-hydroxyflavone as fluorophore and acrylate group as recognition unit. The probe HFAC was characterized by ¹H NMR, ¹³C NMR and HRMS-ESI. The results of absorption and fluorescence spectral analysis indicated that the probe had high sensitivity and selectivity towards cysteine (Cys), and the detection was not affected by other biothiols such as homocysteine, glutathione and others. Meanwhile, it was confirmed that HFAC was a reaction type "off-on" fluorescent probe, the fluorescence intensity at 525 nm had a high linear relationship with Cys concentration in the range of 20-400 μmol/L with a regression equation of y=0.4608x + 3.994 (R²=0.9987) and a detection limit of 37.9 nmol/L, and the color of the reaction solution changed from colorless to bright green at UV light of 365 nm. Fluorescence bioimaging experiment proved that probe HFAC had excellent cell membrane permeability, low cytotoxicity and biocompatibility, which was desirable for fast detection and visualization of both endogenous and exogenous Cys in A549 cells.
- Flavonol,
- Cysteine,
- Fluorescent probe,
- Bioimaging
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沈阳化工大学材料科学与工程学院沈阳 110142