Enhanced fluorescence probe for detecting carboxylesterase 1 (CES1) as well as preparation method and application thereof
A fluorescent probe, carboxylesterase technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of deviation of detection results, cumbersome preparation methods, limited application, etc., to promote the recovery of fluorescent signals , Excellent detection specificity, the effect of expanding the scope of application
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[0039]Example 1: Preparation process flow 1 of probe compound 3-bromomethyl-2-oxo-2H-chromene-7-acetate
[0040] 1090 mg of 3-methyl-2-oxo-2H-chromene-7-acetate (5 mmol), 890 mg of N-bromosuccinimide (5 mmol) and 0.82 mg of azobisisobutyronitrile were dissolved in 30 mL of tetrachloroethylene In the carbonization, the mixed solution was heated to reflux, and the reaction temperature was controlled to be 80 ° C to carry out the reaction, the reaction was stopped after 4 hours of reaction, cooled to room temperature, the mixed solution was subjected to suction filtration, the organic filtrate was collected, and the organic solvent was removed by rotary evaporation. Purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V=4:1) to obtain 1115 mg of white solid (yield: 75.1%). The product was characterized by H NMR spectroscopy, and the results were as follows figure 2 As shown, the characterization data is as follows: 1 H NMR (600MHz, CDCl 3 ): ...
Example Embodiment
[0041] Example 2: Preparation process flow 2 of probe compound 3-bromomethyl-2-oxo-2H-chromene-7-acetate
[0042] 545 mg 3-methyl-2-oxo-2H-chromene-7-acetate (2.5 mmol), 400 mg N-bromosuccinimide (2.25 mmol) and 0.41 mg azobisisobutyronitrile were dissolved in 15 mL In carbon tetrachloride, the mixed solution was heated to reflux, and the reaction temperature was controlled to be 83 ° C to carry out the reaction, the reaction was stopped after 4.5 hours, cooled to room temperature, the mixed solution was subjected to suction filtration, the organic filtrate was collected, and the organic solvent was removed by rotary evaporation, The obtained solid was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V=4:1) to obtain 487 mg of white solid (yield 72.9%). The characterization of the probe 3-bromomethyl-2-oxo-2H-chromene-7-acetate compound in this example is the same as that in Example 1.
Example Embodiment
[0043] Example 3: Preparation Process 3 of Probe Compound 3-Bromomethyl-2-oxo-2H-chromene-7-acetate
[0044] 1635 mg of 3-methyl-2-oxo-2H-chromene-7-acetate (7.5 mmol), 1270 mg of N-bromosuccinimide (7.125 mmol) and 1.23 mg of azobisisobutyronitrile were dissolved in 50 mL In carbon tetrachloride, the mixed solution was heated to reflux, and the reaction temperature was controlled to be 85 ° C to carry out the reaction, the reaction was stopped after 5 hours of reaction, cooled to room temperature, the mixed solution was subjected to suction filtration, the organic filtrate was collected, and the organic solvent was removed by rotary evaporation, The obtained solid was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V=4:1) to obtain 1508 mg of white solid (yield 71.3%). The characterization of the probe 3-bromomethyl-2-oxo-2H-chromene-7-acetate compound in this example is the same as the result in Example 1.
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