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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

Inactive Publication Date: 2017-08-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation method of this kind of probe is cumbersome, and it takes two reactions to show the results; luciferase is easy to inactivate, and the test results are prone to relatively large deviations; the pH buffer used in subsequent tests is limited to 6.5, and no further investigation As a result of the wide pH range, the application is limited; the highly toxic sodium cyanide is used in the preparation process, which is not conducive to large-scale industrial production

Method used

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  • Enhanced fluorescence probe for detecting carboxylesterase 1 (CES1) as well as preparation method and application thereof
  • Enhanced fluorescence probe for detecting carboxylesterase 1 (CES1) as well as preparation method and application thereof
  • Enhanced fluorescence probe for detecting carboxylesterase 1 (CES1) as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]Embodiment 1: Preparation process 1 of probe compound 3-bromomethyl-2-oxo-2H-chromene-7-acetate

[0040] Dissolve 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 in 30 mL of tetrachloro In carbonization, heat the mixed solution to reflux, control the reaction temperature to 80°C for reaction, stop the reaction after 4 hours of reaction, cool to room temperature, filter the mixed solution with suction, collect the organic filtrate, and remove the organic solvent by rotary evaporation to obtain a solid Purification by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V=4:1) gave 1115 mg of white solid (yield 75.1%). The product was characterized by proton nuclear magnetic resonance spectroscopy, and the results were as follows: figure 2 As shown, the characterization data are as follows: 1 H NMR (600MHz, CDCl 3 ): δ7.85(s,1H),7.51(d,J=8.5Hz,1H),7.14(d,J=2.1Hz,...

Embodiment 2

[0041] Embodiment 2: Preparation process 2 of probe compound 3-bromomethyl-2-oxo-2H-chromene-7-acetate

[0042] Dissolve 545 mg of 3-methyl-2-oxo-2H-chromene-7-acetate (2.5 mmol), 400 mg of N-bromosuccinimide (2.25 mmol) and 0.41 mg of azobisisobutyronitrile in 15 mL In carbon tetrachloride, heat the mixed solution to reflux, control the reaction temperature to 83°C for reaction, stop the reaction after 4.5 hours of reaction, cool to room temperature, suction filter the mixed solution, collect the organic filtrate, and remove the organic solvent 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.

Embodiment 3

[0043] Embodiment 3: Preparation process 3 of probe compound 3-bromomethyl-2-oxo-2H-chromene-7-acetate

[0044] Dissolve 1635mg of 3-methyl-2-oxo-2H-chromene-7-acetate (7.5mmol), 1270mg of N-bromosuccinimide (7.125mmol) and 1.23mg of azobisisobutyronitrile in 50mL In carbon tetrachloride, heat the mixed solution to reflux, control the reaction temperature to 85°C for reaction, stop the reaction after 5 hours of reaction, cool to room temperature, suction filter the mixed solution, collect the organic filtrate, and remove the organic solvent 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 that in Example 1.

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Abstract

The invention discloses an enhanced fluorescence probe for detecting carboxylesterase 1 (CES1) as well as a preparation method and application thereof, and belongs to the technical field of fluorescence probe materials. The fluorescence probe refers to 3-bromomethyl-2-oxo-2H-chromen-7-acetate, and the preparation method comprises the flowing steps of (1) dissolving 3-methyl-2-oxo-2H-chromen-7-acetate, N-bromosuccinimide and azodiisobutyronitrile in carbon tetrachloride to obtain a mixed solution; (2) heating the mixed solution for refluxing, and cooling to room temperature after the reaction, performing separation and purification on a reaction product, so as to obtain the 3-bromomethyl-2-oxo-2H-chromen-7-acetate. The fluorescence probe can be used for realizing fluorescence enhanced detection on the CES1; has the advantages of effectiveness, perceptual intuition and easiness in observation; is high in stability, and capable of avoiding interference of external conditions; improves the accuracy of the detection; and is capable of being widely applied to the qualitative and quantitative analysis on the CES1 in environment samples, chemical samples and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe materials, and in particular relates to an enhanced fluorescent probe for detecting carboxylesterase 1 (CES1) and its preparation method and application. Background technique [0002] Carboxylesterase (CES) is a polyprotein, which has the ability to catalyze the hydrolysis of various ester compounds, and release alcohol, carboxylic acid and water molecules after hydrolysis. Based on the characteristic that carboxylesterase can catalyze a variety of ester substrates, carboxylesterase has been widely used in industrial production, organic synthesis, drug activator and other practical applications. Carboxylesterase is mainly divided into two subtypes: carboxylesterase 1 (CES1) and carboxylesterase 2 (CES2), both of which have obvious differences in catalytic performance: CES1 will preferentially and selectively catalyze the hydrolysis energy Obtain small fragments (without benzene ring str...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/6428G01N2021/6432
Inventor 吴水珠倪萌李博文曾钫
Owner SOUTH CHINA UNIV OF TECH
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