Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application thereof in H2O2 detection fluorescent biosensor

A chitosan derivative, 6-OH technology, applied in fluorescence/phosphorescence, material excitation analysis, etc., can solve the problems of limited solubility of derivatives, difficult to dissolve, and limited applications.

Inactive Publication Date: 2013-05-08
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the derivatives prepared by this method have limited solubility in water and are difficult to dissolve in organic solvents, which limits their further application.

Method used

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  • Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application thereof in H2O2 detection fluorescent biosensor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1 (preparation of chitosan 6-OH immobilized cyclodextrin derivatives)

[0079]1 part of chitosan was weighed and dissolved in 200 parts of acetic acid / water solution with a mass concentration of 1%. 2 parts of phthalic anhydride dissolved in 50 parts of ethanol were added dropwise to the reaction system, and the reaction was stirred at 50°C for 5 hours. Then add methanol to precipitate the resulting chitosan derivatives, wash with ethanol more than 2 times to remove excess phthalic anhydride compounds, and then vacuum dry at 60°C to obtain phthalic anhydride-protected chitosan derivatives a .

[0080] 1 part of phthalic anhydride-protected chitosan derivative a is dissolved in 200 parts of DMSO, and 30 parts of chloroform solution of p-toluenesulfonyl chloride are added thereto, wherein the mass concentration of p-toluenesulfonyl chloride is 20% , dripped in 10 minutes, reacted at 30°C for 3 hours, filtered with suction to obtain a light yellow solid, washe...

Embodiment 2

[0086] Embodiment 2 (preparation embodiment of chitosan 6-OH immobilized cyclodextrin derivative)

[0087] Utilize the click chemical reaction of the azide derivative c of chitosan prepared in specific example 1 and the monoalkynylation derivative e of cyclodextrin to prepare phthalic anhydride chitosan immobilized cyclodextrin derivative Object f:

[0088] Weigh 1 part of the azide derivative c of chitosan, dissolve it in 10 parts of DMAc, and weigh 0.03 parts of CuSO 4 ·5H 2 O was dispersed in 5 parts of ethanol, adding 0.03 part of sodium ascorbate and 0.05 part of water to promote dissolution, mixed the solution, weighed 4 parts of monoalkynylated derivative e, added the above solution, stirred and reacted at 60°C for 5 hours, Stop the reaction, add acetonitrile to precipitate, wash with water twice, and vacuum-dry the filter cake at 60° C. to obtain phthalic anhydride chitosan immobilized cyclodextrin derivative f.

[0089] 1 part of obtained phthalic anhydride-based c...

Embodiment 3

[0090] Embodiment 3 (use chitosan 6-OH immobilized cyclodextrin derivative of the present invention to prepare fluorescent biosensor detection material and be used for H 2 o 2 detection)

[0091] The chitosan-immobilized cyclodextrin derivative obtained in Example 1 was dissolved in DMF, wherein the concentration of the chitosan-immobilized cyclodextrin derivative in the solution was 0.025 mol / L. The fluorescent probe coumarin was added to it. In the reaction, the molar ratio of chitosan immobilized cyclodextrin derivative to coumarin was 1:1. The reaction was refluxed and stirred in a 40°C oil bath for 4 hours. After the reaction is completed, the clathrate is precipitated with deionized water, the coumarin that has not been clathrated is washed away with ether, and dried to obtain the chitosan 6-OH immobilized cyclodextrin derivative clathrate fluorescent probe coumarin product. The inclusion rate of coumarin was measured to be 39.2%.

[0092] The chitosan 6-OH immobil...

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Abstract

The invention relates to a preparation method of a chitosan 6-OH immobilized cyclodextrin derivative, and an application thereof in a H2O2 detection fluorescent biosensor. The invention belongs to the field of high-molecular material preparation and modification. According to the invention, chitosan 2-NH2 is protected by using phthalic anhydride; through a click chemical reaction, cyclodextrin is immobilized at a 6-OH position; and the protection of chitosan 2-NH2 is removed by using hydrazine hydrate, such that the chitosan 6-OH immobilized cyclodextrin derivative with good solubility in water and part of organic solvents and with high immobilization rate is prepared. Fluorescent probe is immobilized in cyclodextrin hydrophobic hollow cavities of the chitosan 6-OH immobilized cyclodextrin derivative provided by the invention, 2-NH2 of chitosan pyranose ring is used for immobilizing catalase, and the material is used in a fluorescent biosensor used for detecting H2O2 content. The invention assists in realizing the application of chitosan 6-OH immobilized cyclodextrin derivative in the fluorescent biosensor in which enzyme catalysis is combined with fluorescence detection.

Description

technical field [0001] The present invention relates to a kind of preparation method of chitosan 6-OH immobilized cyclodextrin derivative and its preparation method in H 2 o 2 The application in detecting fluorescent biosensors belongs to the field of preparation and modification of polymer materials. Background technique [0002] Chitosan is rich in sources, low in price, easy to chemically modify, can be combined with enzymes, and has excellent properties such as film-forming, biocompatibility, biodegradability, permeability, hydrophilicity, and mechanical strength. It has important application value in functional membrane materials for biosensors. [0003] Cyclodextrin has a unique internal hydrophobic and external hydrophilic cavity structure, and is an important carrier for fluorescent biosensor detection. Enveloping small organic molecules with photochemical probe properties in the hydrophobic cavity of cyclodextrin can make the probe molecules uniformly dispersed i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08B37/08C08B37/16G01N21/64
Inventor 陈煜叶彦春李伟萍郭燕文
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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