Injectable hyaluronic acid-based hydrogel and preparation method thereof

A technology of hyaluronic acid and sodium hyaluronate, which is applied in the field of injectable hyaluronic acid-based hydrogel and its preparation, can solve the problems of harsh synthesis conditions, complicated synthesis steps, etc., and achieves simple preparation method, mild preparation conditions, The effect of high adjustable space

Active Publication Date: 2020-07-24
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of hyaluronic acid-based hydrogel by chemical cross-linking in the prior art has problems such as too complicated synthesis steps, too harsh synthesis conditions, and the degradation rate can only be controlled by controlling the cross-linking network density.

Method used

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  • Injectable hyaluronic acid-based hydrogel and preparation method thereof
  • Injectable hyaluronic acid-based hydrogel and preparation method thereof
  • Injectable hyaluronic acid-based hydrogel and preparation method thereof

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preparation example Construction

[0051] The preparation method of described linking agent comprises the following steps:

[0052] A) reacting 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester with polyethylene glycol whose end group is an amino group to obtain a reaction product;

[0053] B) Deprotecting the reaction product to obtain a crosslinking agent.

[0054] Wherein, the reaction process is as follows:

[0055]

[0056] In the present invention, 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester and polyethylene glycol whose end group is amino are dissolved in an organic solvent, Reaction in the presence of the agent, precipitation, to obtain the reaction product.

[0057] The molar equivalent of the 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester is 1.2 to 5 molar equivalents of the amino group in polyethylene glycol whose end group is an amino group. times, preferably 2 times; the organic solvent is preferably anhydrous...

Embodiment 1

[0120] in N 2 Under atmosphere, add 12.0g of hydrazine hydrate and 20mL of absolute ethanol solution to the round bottom flask, adjust the temperature of the oil bath to 90°C, add 10.0g of dimethyl 3,3'-dithiodipropionate, stir and reflux After 5 hours, the obtained product was recrystallized three times from a mixed solution of ethanol: water = 5% (V / V) to prepare 3,3'-dithiobis(hydrazine propionate). see figure 1 and figure 2 , figure 1 For the preparation of 3,3'-dithiobis(hydrazine propionate) prepared in Example 1 of the present invention; figure 2 The mass spectrum of 3,3'-dithiobis(hydrazine propionate) prepared for Example 1 of the present invention.

Embodiment 2

[0122] Weigh 1.2g of sodium hyaluronate and add it into 200mL of ultrapure water and stir until it is completely dissolved, then add 5.2g of adipic acid dihydrazide, 0.4g of 1-hydroxybenzotriazole, 58mg of 1-(3-dimethylamino Propyl)-3-ethylcarbodiimide hydrochloride, stir to make it completely dissolved, then use 0.01M dilute hydrochloric acid solution to adjust the pH of the system to 4.7, stir and react at 25°C for 72 hours, and use a 7000Da dialysis bag to obtain the product After dialysis for 72 hours, the product hyaluronic acid-graft-adipate dihydrazide was obtained.

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Abstract

The invention provides an injectable hyaluronic acid-based hydrogel, which is prepared by mixing modified hyaluronic acid, a cross-linking agent and a solvent, wherein the cross-linking agent comprises a repeating unit having a structure represented by a formula (I) and an end group having a structure represented by a formula (II). The modified hyaluronic acid hydrogel provided by the invention has the advantages of mild preparation conditions, simple preparation method, controllable mechanical strength and degradation rate, good application prospect in the field of biomedicine, and high adjustable space, so that hydrogel materials with various different physical and chemical properties are prepared by adjusting the molecular weight of hyaluronic acid, the grafting rate of adipic dihydrazide or 3,3'-dithiobis(hydrazine propionate), the molecular weight of a cross-linking agent and the like according to different requirements,.

Description

technical field [0001] The invention belongs to the technical field of polysaccharide polymer materials, and in particular relates to an injectable hyaluronic acid-based hydrogel and a preparation method thereof. Background technique [0002] Hydrogel is a kind of special soft-wet material with three-dimensional network structure cross-linked by chemical bonds, hydrogen bonds, van der Waals force or physical entanglement, which can swell but not dissolve in water or biological fluids, and has both solid and Two properties of liquid. This feature makes it widely used in biomedical fields such as tissue engineering and drug delivery. Since the three-dimensional space network structure of hydrogel is similar to natural extracellular matrix, hydrogel materials can provide support and metabolic space for cell adhesion, proliferation and growth. In the swollen state, the network of the hydrogel is filled with a large amount of water, which facilitates the transport of oxygen, nu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/075C08J3/24C08L5/08C08L71/02C08B37/08C08G65/333
CPCC08B37/0072C08G65/33341C08J3/075C08J3/246C08J2305/08C08J2371/02C08J2405/08C08J2471/02
Inventor 贺超良任慧张震陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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