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Near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, preparation method and applications thereof

A butyrylcholinesterase and fluorescent probe technology, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of large changes, easy detection, and low background value

Active Publication Date: 2018-06-22
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are few reports on the use of specific substrate-type fluorescent probes for detecting the activity of butyrylcholinesterase (EC number: 3.1.1.8) at home and abroad.

Method used

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  • Near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, preparation method and applications thereof
  • Near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, preparation method and applications thereof
  • Near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, preparation method and applications thereof

Examples

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preparation example Construction

[0026] In a second aspect, the present invention also provides a method for preparing the near-infrared semicyanine fluorescent probe as described above, including: wherein, in the presence of a nucleophilic reaction condition and an acid-binding agent, in an organic solvent, the formula (2) The compound of the shown structure is contacted with cyclopropylformyl chloride;

[0027]

[0028] In the preparation method of the near-infrared semicyanine fluorescent probe of the present invention, the nucleophilic reaction is the reaction between the hydroxyl group in the formula (2) and cyclopropylformyl chloride, and the conditions of the nucleophilic reaction include a temperature of Minus 5°C to 30°C, the time is 10-200min, preferably, the condition of the nucleophilic reaction is that the temperature is 0-25°C, and the time is 80-160min.

[0029] In the preparation method of the near-infrared semicyanine fluorescent probe of the present invention, the contact needs to be carr...

preparation example 1

[0075] This example is used to illustrate the preparation method of the near-infrared semicyanine fluorescent probe of the present invention.

[0076] In an organic solvent (dichloromethane, 20mL), in the presence of an acid-binding agent (triethylamine, 2mmol), the compound (1mmol) represented by formula (2) and cyclopropylformyl chloride (2mmol) were mixed at 5°C Next, maintain the contact of 120min, obtain the material after contact. Then, the contacted material was washed with water (50 mL) and saturated saline solution (50 mL) successively to obtain the washed material. The organic phase in the washed material was separated and dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was purified by a silica gel column to obtain 0.27 g of a white solid product.

[0077] 1 H NMR (400MHz, DMSO-d 6): δ8.95(d, J=4.0Hz, 1H), 8.02(s, 1H), 7.87(s, 1H), 7.42(d, J=8.0Hz, 2H), 7.25(t, J=6.0Hz ,1H),6.81(s,1H),6.53(s...

Embodiment 1

[0085] This example is used to illustrate the method for detecting the activity of butyrylcholinesterase by the compound represented by formula (1) provided by the present invention.

[0086] Dissolve 1 mg of butyrylcholinesterase sample in 10 mM phosphate buffer (pH=7.0) and carry out gradient dilution, prepare butyrylcholinesterase standard solution of different concentrations according to the concentration given in Table 1, and configure The obtained butyrylcholinesterase standard solution was preheated in a constant temperature water bath at 30°C; at the same time, a black flat-bottomed 96-well plate was placed in a 30°C incubator to preheat. Subsequently, each took 40 μL of preheated butyrylcholinesterase standard solution in a preheated black flat-bottomed 96-well plate, then added 120 μL of 10 mM phosphate buffer (pH=7.4), and set up a negative control group (only 160 μl buffer), under dark conditions, 40 μL of 10 μM infrared semicyanine fluorescent probe with the struc...

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Abstract

The invention relates to the field of detection of butyrylcholinesterase, and discloses a near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, a preparation method and applications thereof, wherein specifically the near-infrared hemicyanine-based fluorescent probe has a structure represented by a formula (1). The method comprises that a compound represented by a formula (2) contacts cyclopropanecarboxylic acid chloride in an organic solvent under a nucleophilic reaction condition in the presence of an acid binding agent. The applications comprise: applicationsin the detection of the activity of butyrylcholinesterase, and a detection method and a detection kit for the activity of butyrylcholinesterase. The near-infrared hemicyanine-based fluorescent probeof the present invention has advantages of high sensitivity, good selectivity, high fluorescence intensity change, easy detection, high stability, convenient use and low cost in the application related to the detection of the activity of carboxypeptidase Y. The formulas (1) and (2) are defined in the specification.

Description

technical field [0001] The present invention relates to the field of detection of butyrylcholinesterase, in particular to a near-infrared semicyanine fluorescent probe, a preparation method of the near-infrared semicyanine fluorescent probe and its ability to detect butyrylcholinesterase The application in the activity, and a detection method of the activity of butyrylcholinesterase and the detection kit of the activity of butyrylcholinesterase. Background technique [0002] Butyrylcholinesterase (BChE) mainly exists in organisms as an isoenzyme of acetylcholinesterase, which is a non-specific esterase synthesized by the liver, because the enzyme is released into the plasma immediately after synthesis in the liver Therefore, BChE activity in serum is a sensitive indicator for determining the protein synthesis function of hepatocytes. With the continuous improvement of detection technology and clinical diagnosis and treatment, butyrylcholinesterase is not only used to evalua...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64C07D413/10
CPCC07D413/10C09K11/06C09K2211/1018G01N21/6428
Inventor 杨光富杨文超杨庶侯
Owner HUAZHONG NORMAL UNIV
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