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Fluorescent probe for detecting activity of butyrylcholineesterase, preparation method and application thereof

A technology of butyrylcholinesterase and fluorescent probes, applied in the field of fluorescent probes, can solve problems such as no public detection function, achieve good sensitivity and avoid interference effects

Active Publication Date: 2019-08-16
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Patent No. 2013106811585 discloses a long-wavelength fluorescent probe and its preparation method and application. The compound used as the probe is 1,7-dimethyl-3,5-distyryl-8-benzene Base-(2'-maleimide)-boron difluoride dipyrromethane has good selectivity to sulfhydryl compounds, and the fluorescence intensity increases after reacting with sulfhydryl groups, but the long-wavelength fluorescent probe is not disclosed in the patent. BChE has detection function

Method used

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  • Fluorescent probe for detecting activity of butyrylcholineesterase, preparation method and application thereof
  • Fluorescent probe for detecting activity of butyrylcholineesterase, preparation method and application thereof
  • Fluorescent probe for detecting activity of butyrylcholineesterase, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. Synthesis of 2,3-dicyano-1,4-phenylene diacrylate (DCPDA for short).

[0040] The steps of synthesizing DCPDA are as follows:

[0041] First, 0.5 g (ie 3.1 mmol) of 2,3-dicyanohydroquinone was dissolved in 50 mL of dry THF, and then 2.0 mL of excess acryloyl chloride was added dropwise. After adding a small amount of triethylamine, the resulting mixture was stirred well for 24 hours. Finally, the solvent was removed by a rotary evaporator, and the product was purified by silica gel column chromatography (ethyl acetate:petroleum ether 1:4). The final product DCPDA is a white powder with a yield of 36%. The NMR spectrum and high-resolution mass spectrum of the DCPDA and the structural formula of DCPDA are detailed in Figure 2 to Figure 4 shown.

[0042] The reaction formula of 2,3-dicyanohydroquinone and acryloyl chloride is as follows:

[0043] R-COCl+R'OH→RCOOR'+HCl

[0044] 2. The fluorescence response of 2,3-dicyano-1,4-phenylene diacrylate (DCPDA) to mercapto ...

Embodiment 2

[0063] 1. Synthesis of 2,3-dicyano-1,4-phenylene bis(3,3-dimethacrylate) (DCPDMA).

[0064] Synthetic DCPDMA steps are as follows:

[0065] First, 0.5 g (substance amount: 3.1 mmol) of 2,3-dicyanohydroquinone was dissolved in 50 mL of dry THF, and then 2.0 mL of excess 3,3-dimethylacryloyl chloride was added dropwise. After adding a small amount of triethylamine, the resulting mixture was stirred well for 24 hours. Finally, the solvent was removed by a rotary evaporator, and the product was purified by silica gel column chromatography (ethyl acetate:petroleum ether 1:4). The final product was a white powder with a yield of 36%.

[0066] The reaction formula of 2,3-dicyanohydroquinone and 3,3-dimethylacryloyl chloride is as follows:

[0067] R-COCl+R'OH→RCOOR'+HCl

[0068] 2. The fluorescence response of 2,3-dicyano-1,4-phenylene bis(3,3-dimethacrylate) (DCPDMA) to mercapto compounds.

[0069] Add a certain amount of DCPDMA solution into 3.0mL HEPES buffer solution, wherei...

Embodiment 3

[0085] 1. Synthesis of 2,3-dicyano-1,4-phenylene bis(4,4,4-trifluorobutenoate) (DCPDFC).

[0086] The steps of synthesizing DCPDFC are as follows: First, 0.5 g (the amount of substance is 3.1 mmol) of 2,3-dicyanohydroquinone is dissolved in 50 mL of dry THF, and then excessive 4,4,4-trifluoroquinone is added dropwise. Crotonoyl chloride 2.0 mL. After adding a small amount of triethylamine, the resulting mixture was stirred well for 24 hours. Finally, the solvent was removed by a rotary evaporator, and the product was purified by silica gel column chromatography (ethyl acetate:petroleum ether 1:4). The final product was a white powder with a yield of 36%.

[0087] The reaction formula of 2,3-dicyanohydroquinone and 4,4,4-trifluorocrotonoyl chloride is as follows:

[0088] R-COCl+R'OH→RCOOR'+HCl

[0089] 2. The fluorescence response of 2,3-dicyano-1,4-phenylene bis(4,4,4-trifluorobutenoate) (DCPDFC) to mercapto compounds.

[0090] Add 90 μL of DCPDFC solution at a concentra...

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Abstract

The invention discloses a fluorescent probe for detecting activity of butyrylcholineesterase. The molecular structure of the fluorescent probe is shown in the specification. A preparation method of the fluorescent probe comprises the following steps: step 1, dissolving 2,3-dicyanohydroquinone in dried tetrahydrofuran; step 2, dropwise adding excessive amount of one of acryloyl chloride, 3,3-dimethylacryloyl chloride or 4,4,4-trifluorobutenoyl chloride into the mixed solution in the step 1; step 3, dropwise adding a small amount of triethylamine into the mixed solution obtained in the step 2; 4, stirring the mixed solution obtained in the step 3, removing the solvent by using a rotary evaporator, and purifying the product by using silica gel column chromatography to finally obtain white powder. The fluorescent probe provided by the invention is used for detecting the activity of butyrylcholine esterase. The probe can be lighted by mercaptan through rapid mercaptoalkene click reaction torealize fluorescence enhancement, and has good selectivity and strong anti-interference performance.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe for detecting the activity of butyrylcholinesterase and its preparation method and application. Background technique [0002] Thiol-reactive probes are commonly used to label proteins to monitor conformational changes, assembly of multiple subunits, and ligand binding processes, and are frequently used to detect small biothiol molecules such as glutathione, which are important in human health and important role in disease. At present, the existing thiol-reactive fluorescent probes have the disadvantage of no specific selectivity for all sulfhydryl-containing substances, and there is an urgent need to design and develop new selective recognition fluorescent probes for glutathione, cysteine, and homocysteine. probe. Among these specific recognition probes, the acryloyl functionalized molecular probes showed better performance in terms of selectivity...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C255/55C07C253/30G01N21/64
CPCC09K11/06C07C255/55G01N21/6428C09K2211/1007
Inventor 丰慧钱兆生陈桂林
Owner ZHEJIANG NORMAL UNIVERSITY
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