4.7 Article

BODIPY-based naked-eye fluorescent on-off probe with high selectivity for H2S based on thiolysis of dinitrophenyl ether

Journal

SENSORS AND ACTUATORS B-CHEMICAL
Volume 290, Issue -, Pages 551-557

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.snb.2019.03.141

Keywords

BODIPY; Fluorescent dye; Cleavage; Probe; Electron transfer

Funding

  1. National Natural Science Foundation of China [21542004]
  2. Young and middle-aged scientific and technological innovation talents of Shenyang Science and Technology Bureau [RC170140]
  3. Liaoning Province Natural Science Foundation [20170540721]
  4. Basic research on the application of Industrial Development of Shenyang Science and Technology Bureau [18013027]
  5. Chinese Scholarship Council [20183058]
  6. Distinguished Professor Project of Liaoning province

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1-(2-Hydroxyphenyl) ethanone as a starting material, BODIPY 3 bearing 2,4-dinitrophenyl (DNP) group was prepared in total 7% yield. Probe 3 was strongly fluorescent. Sulfhydryl-specific cleavage reaction released the hydroxyl group. Due to the electron transfer of the hydroxyl group in 2 to the BODIPY core, dye 2 was weakly fluorescent. Naked-eye and fluorescent turn-off probe 3 was highly selective and sensitive to H2S, and could be used to detect HS- in HCT-116 and CT-26 cells, indicating its potential application for studying the effect of HS- in biological system.

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