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Tetraphenylethylene compound containing sialic acid glycosyl unit, preparation method and application

A technology of sialic acid sugar and tetraphenylethylene, which is applied in the field of fluorescent probe research to achieve the effects of enhanced fluorescence intensity, improved detection sensitivity, good photostability and chemical stability

Active Publication Date: 2020-10-02
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After these detection substrates interact with sialidase, their optical signals either depend on further color reaction, or are affected by the optical properties of the detection molecules themselves, which have certain limitations in practical applications.

Method used

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  • Tetraphenylethylene compound containing sialic acid glycosyl unit, preparation method and application
  • Tetraphenylethylene compound containing sialic acid glycosyl unit, preparation method and application
  • Tetraphenylethylene compound containing sialic acid glycosyl unit, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of Compounds of Formula I.

[0028] attached figure 1 A synthetic route diagram for the compound of formula I is shown.

[0029] Step A: Methyl N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-oxazolidinone-2-(3-azidopropoxy)sialate (compound 1)

[0030] Molecular sieves are added to the long reaction flask, heated and burned to remove water, and after cooling, add N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-oxazolidinone-protected sialic acid p-methylglucosinolate (compound 1-1, 136.4mg, 0.235mmol), p-tolylsulfoxide (108.1mg, 0.469mmol), seal the reaction tube, replace the gas with argon 3 times, add anhydrous dichloromethane (8 mL). The reaction tube was stirred at -70°C for 15 minutes, trifluoromethanesulfonic anhydride (47 μL) was added with a micro syringe, stirred at -70°C for 30 minutes, 3-azido-1 propanol (35.6 mg, 0.352 mmol) was added Dichloromethane (2 mL) solution. The reaction was stirred at -70°C for 2 hours and then at -50°C for 2 hours. Triethylamine (0.2 ...

Embodiment 2

[0038] Synthesis of Compounds of Formula II.

[0039] attached figure 2 A synthetic route diagram for the compound of formula II is shown.

[0040] Step A: Methyl N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-oxazolidinone-2-(3-azidopropoxy)sialate (Compound 1), prepared according to the method described in step A of Example 1.

[0041] Step B: Tetrapropargylpentaerythritol (compound 2)

[0042] Pentaerythritol (1.3615g, 10mmol) was dissolved in N,N-dimethylformamide (35mL), oil-dispersed sodium hydride (120mmol) was slowly added in an ice-salt bath, and after stirring for 30 minutes, propargyl Bromine (6 mL). After the reaction solution was reacted at 40° C. for 2.5 hours, 3 mL of propargyl bromide was added. The reaction solution was placed in an oil bath at 50°C for 16 hours. After cooling to room temperature, the reaction was quenched by adding water and extracted twice with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated. ...

Embodiment 3

[0053] Formula I compound detection sialidase performance test

[0054] 1) Principle: sialidase can act on natural or synthetic sialyl glycoside substrates. After the target compound reacts with sialidase, the glycosidic bond is broken, the solubilizing sialic acid unit leaves, the solubility of the molecule decreases, and aggregation occurs induced luminescence. The activity of sialidase can be detected sensitively through the change of fluorescence.

[0055] 2) Test material:

[0056] Commercially available sialidase (the sialidase is produced by Clostridium perfringens, one unit of activity is defined as: one unit of this enzyme is produced at pH 5.0 and 37°C with sialic acid (2→3) lactose as the substrate The product can release 1.0μmol N-acetylneuraminic acid per minute.

[0057] Phosphate buffer solution: pH 7.1.

[0058] Compound of formula I: 10 mM stock solution.

[0059] 3) Test method:

[0060] Different concentrations of sialidase and the compound of formula ...

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Abstract

The invention relates to detection of sialidase activity by an aggregation induced luminescence probe. In particular, the invention relates to two tetrastyrene compounds containing sialic acid glycosyl units, and a preparation method and an application thereof in sialidase detection. The compounds disclosed by the invention have the structures shown in the formulas (I and II). Three or four sialicacid glycosyl units are contained and the sialic acid glycosyl units are connected onto tetrastyrene through triazole and pentaerythritol. The compounds can be applied to detection of sialidase and have application value in the diagnosis of diseases related to sialidase.

Description

technical field [0001] The present invention relates to the research field of fluorescent probes based on the aggregation-induced luminescent effect. Specifically, the present invention relates to two polysialoglycosyl-containing tetraphenylethylene compounds linked by triazole and / or pentaerythritol, the preparation method and Its application in the detection of sialidase activity. Background technique [0002] Sialidase, namely neuraminidase, whose enzymatic code is EC 3.2.1.18, can catalyze the hydrolysis of natural or synthetic α-sialoglycoside compounds. Sialidase is widely found in bacteria, viruses and animal cells. For example, bacteria that can produce sialidase include Streptococcus pneumoniae, Clostridium perfringens, Vibrio cholerae, etc.; viruses include influenza virus, mumps virus, Sendai virus Wait. Many diseases that endanger human health are related to sialidase. For example, Vibrio cholerae sialidase can decompose gangliosides on the surface of intestina...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C07H1/00C09K11/06G01N21/64
CPCY02P20/55
Inventor 邢国文刘广建
Owner BEIJING NORMAL UNIVERSITY
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