Hyaluronic acid derivative and preparation method for hyaluronic acid hydrogel

A technology of hyaluronic acid and derivatives, which is applied in the field of biomedical material preparation to achieve stable performance, controllable modification reaction and simple operation

Active Publication Date: 2014-04-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Hyaluronic acid derivative and preparation method for hyaluronic acid hydrogel
  • Hyaluronic acid derivative and preparation method for hyaluronic acid hydrogel
  • Hyaluronic acid derivative and preparation method for hyaluronic acid hydrogel

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Embodiment 1

[0059] Hyaluronic acid-butenediolate derivatives were prepared as follows:

[0060] (1) Weigh 0.2 g of hyaluronic acid (about 0.527 mmol, the molecular weight of its structural unit is 379.32 g / mol, the same below) into 100 mL of anhydrous formamide, stir at 50°C until fully dissolved;

[0061] (2) Weigh 0.517 g of maleic anhydride (about 5.27 mmol, molecular weight of 98.06 g / mol) and dissolve it in anhydrous formamide, and add it to the above solution (1) under stirring conditions. The molar number of maleic anhydride is hyaluronic acid 10 times the number of moles of reactive hydroxyl groups on the acid;

[0062] (3) No catalyst is added;

[0063] (4) React at 50°C for 5 h. After the reaction solution is cooled to room temperature, add it dropwise to 500 mL of cold absolute ethanol under stirring to precipitate the reaction product;

[0064] (5) Centrifuge the above solid-liquid mixture at high speed, disperse and centrifuge the precipitate in absolute ethanol, and repeat...

Embodiment 2

[0068] Hyaluronic acid-4-pentenoate derivatives were prepared as follows:

[0069] (1) Weigh 0.4 g of hyaluronic acid (about 1.06 mmol) into 100 mL of anhydrous tetrahydrofuran, stir at 60°C until fully dissolved;

[0070] (2) Weigh 0.961 g 4-pentene anhydride (about 5.27 mmol, molecular weight 182.22 g / mol) and dissolve it in anhydrous tetrahydrofuran, add it to the above solution (1) under stirring condition, the mole number of 4-pentene anhydride It is 5 times the number of moles of reactive hydroxyl groups on hyaluronic acid;

[0071] (3) Add 0.1g of DMAP catalyst to the above reaction solution;

[0072] (4) React at 60°C for 10 h. After the reaction solution is cooled to room temperature, add it dropwise to 800 mL of cold anhydrous isopropanol under stirring to precipitate the reaction product;

[0073] (5) Centrifuge the above solid-liquid mixture at high speed, disperse and centrifuge the precipitate in anhydrous isopropanol, and repeat this step 2-4 times;

[0074] ...

Embodiment 3

[0076] A single-component hyaluronic acid-butene ester hydrogel was prepared as follows:

[0077] Weigh 20 mg of hyaluronic acid-butenediolate derivatives sealed after freeze-drying, dissolve in 1.0 mL containing 0.1% 2-hydroxy-4'-(hydroxyethoxy)-2-methylpropiophenone ( I2959) Aqueous solution of initiator; after taking an appropriate volume of the solution in a specific mold, at a wavelength of 365nm and a light intensity of 30mW / cm 2 The UV radiation for 120s initiates the polymerization reaction to form hyaluronic acid hydrogel.

[0078] The single-component hyaluronic acid-butenediolate hydrogel obtained by DMA is used for detection, and the dynamic force frequency is 1.0Hz and 10Hz. The detection results are as follows: figure 2 shown. It can be seen from the figure that the average storage modulus of the hydrogel is above 0.2 MPa.

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Abstract

The invention discloses a hyaluronic acid derivative and a preparation method thereof. The preparation method comprises the following steps: carrying out hybrid reaction on hyaluronic acid/salt and anhydride in an anhydrous solvent, and precipitating, separating and purifying the product, so that the hyaluronic acid derivative with cross-linkable performance is obtained. The preparation method is simple in process, the reaction degree can be controlled through controlling the reaction parameter, and the product obtained through the method is stable in property, and can be kept for a long time; in addition, the obtained hyaluronic acid derivative with the cross-linkable performance can be used for preparing hyaluronic acid hydrogel under a mild condition, has an excellent biocompatibility, and can be applied to the carrier material of a bio-active substance, a tissue engineering scaffold material and a soft tissue filling material.

Description

technical field [0001] The invention relates to a preparation method of a hyaluronic acid derivative and a hydrogel thereof, belonging to the field of preparation of biomedical materials. technical background [0002] Due to its unique composition and structural characteristics, hyaluronic acid has excellent water retention performance. At the same time, it has attracted much attention in the field of tissue engineering due to its good biocompatibility and biodegradability. application value. In the research and application of hyaluronic acid, it is usually necessary to chemically modify it to achieve intramolecular or intermolecular cross-linking of hyaluronic acid, or cross-link with other raw materials to form composite materials with covalent bonds, so as to obtain more hyaluronic acid. Biomedical materials with ideal mechanical properties, biodegradability, plasticity and functionality. [0003] In existing reports, there are two types of chemical modification methods...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08J3/075C08J3/24C08J3/28C08L5/08C08F299/00C08F2/48A61L27/20A61L27/52A61L27/54A61L31/04A61L31/14A61L31/16
Inventor 林海樊渝江张兴栋
Owner SICHUAN UNIV
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