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A fluorescent probe for detecting butyrylcholinesterase activity and its synthesis method and application

A butyrylcholinesterase and fluorescent probe technology, which is applied in the field of butyrylcholinesterase activity detection, can solve the problems of unfavorable BChE determination, reduced accuracy, and low sensitivity, and achieve the effect of avoiding fluorescence background interference

Active Publication Date: 2022-04-19
QINGDAO UNIV OF SCI & TECH
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Problems solved by technology

For the first three methods, it is difficult to avoid the problems of complex operation, low sensitivity and poor stability, which hinder their further application
However, although the DTNB assay has high sensitivity with thiobutyrylcholine as the substrate, it may be less accurate due to potential interference from the detection system
And in the hydroxylamine colorimetric method, acetylcholine is used as a reactive substrate, which is not conducive to the determination of BChE, resulting in an inevitable decrease in detection sensitivity

Method used

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  • A fluorescent probe for detecting butyrylcholinesterase activity and its synthesis method and application
  • A fluorescent probe for detecting butyrylcholinesterase activity and its synthesis method and application
  • A fluorescent probe for detecting butyrylcholinesterase activity and its synthesis method and application

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Embodiment 1

[0056] Embodiment 1: the synthesis of fluorescent probe

[0057] 1. Synthesis steps:

[0058] (1) Dissolve 4-(diethylamino)salicylaldehyde (0.97g, 5.0mmol) and triethylamine (1.40mL, 10.0mmol) in 20mL of anhydrous dichloromethane at 0°C, then add in Cyclopropanecarbonyl chloride (0.63 g, 6.0 mmol) in 10 mL of dichloromethane, the mixture was stirred at room temperature overnight; after quenching the reaction, the solution was washed 3 times with brine, and the organic phase was dried over anhydrous sodium sulfate and then distilled under reduced pressure The solvent was removed, and the crude product was purified by column chromatography (PE:EA=10:1), to obtain compound 1 with a yield of 83%, and the reaction process is shown in formula (1):

[0059]

[0060] (2) Weigh 1.25g (10.0mmol) 2-aminobenzenethiol and 0.8g (12.0mmol) malononitrile, dissolve in 20mL absolute ethanol, add 0.5mL acetic acid, stir and react at room temperature for 5h, extract and separate, and Pressur...

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Abstract

The invention discloses a fluorescent probe for detecting the activity of butyrylcholinesterase and its synthesis method and application. It discloses a novel butyrylcholinesterase sensor based on the detection of no background signal Under the action of butyrylcholinesterase, the fluorescent signal is transformed from nothing to real, and then the concentration level of butyrylcholinesterase is detected. The fluorescent probe generates the probe P1 by introducing the targeting site of butyrylcholinesterase into the non-emission backbone, avoiding the inherent fluorescent background of the detection probe, and greatly improving the detection sensitivity. After adding butyrylcholinesterase, cyclopropylbutyric acid can be removed, and then spontaneously cyclized in situ to generate a fluorescent product PF as an indicator reflecting BChE activity. The invention not only can greatly improve the detection sensitivity, but also has good selectivity and biocompatibility, and has great potential in the field of clinical diagnosis.

Description

technical field [0001] The invention belongs to the technical field of detection of butyrylcholinesterase activity, and relates to a method strategy for detecting the activity level of butyrylcholinesterase in cells, tissue sections and organisms. More specifically, it relates to a non-emission probe, its synthesis method and its use as an indicator by spontaneous cyclization to generate a fluorophore when detecting butyrylcholinesterase. Background technique [0002] Butyrylcholinesterase (BChE) is also known as pseudocholinesterase or cholinesterase II. Since BuChE is released into the blood immediately after synthesis in the liver, it can be used as a sensitive indicator for evaluating the synthetic function of liver cells. Determination of the concentration of BChE in serum is generally used as a liver function test. It has been reported that BChE is also closely related to complex neurodegenerative diseases such as Alzheimer's disease (AD). With the development of AD, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCC07D277/64C09K11/06G01N21/64G01N21/6428G01N21/6456C09K2211/1007C09K2211/1037G01N2021/6417G01N2021/6443
Inventor 丁彩凤张倩傅彩霞滕葆晖张鹏
Owner QINGDAO UNIV OF SCI & TECH
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