Near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and its preparation method

A technology of hyaluronic acid and articular cartilage, applied in the field of biomedical materials, can solve the problems of poor light penetration ability, high degree of cell damage, and limited application, and achieve the effects of reducing friction coefficient, deep tissue penetration, and improving lubrication Effect

Active Publication Date: 2022-03-29
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, light, as a non-invasive method, has broad application prospects in clinical applications, while traditional photoresponsive materials such as azobenzene, etc., mainly respond to ultraviolet light, but the light penetration ability of ultraviolet wavelengths is poor, and the degree of cell damage high, thus limiting its application in the biomedical field, especially for the design of smart responsive hydrogels for the lubrication repair of cartilage in vivo

Method used

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  • Near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and its preparation method
  • Near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and its preparation method
  • Near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] The preparation method steps of the near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair provided in this example are as follows:

[0080] (1) Preparation of hyaluronic acid (mAzo-HA) modified by azobenzene derivatives

[0081] (11) Preparation of tetra-o-methoxy substituted azobenzene (mAzo)

[0082] Dissolve 1g of granular 2,6-dimethoxyaniline in a mixed solution of 1.2mL of water and 1.5mL of 37wt% hydrochloric acid. After cooling to 2°C, slowly add 4mL of NaNO with a concentration of 1.8mol / L 2 solution and stirred for 20 minutes. At 2°C, slowly add the above mixed solution to the suspension formed by 1 g of 3,5-dimethoxyaniline and 40 mL of water, then add a 2 mol / L sodium bicarbonate solution to adjust the pH of the reaction solution to 8, and stir Overnight (about 12h). Use dichloromethane to extract the reacted solution, separate the liquid from the organic layer with a separatory funnel, concentrate the organic solution by rotary ...

Embodiment 2

[0099] The preparation method steps of the near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair provided in this example are as follows:

[0100] (1) Preparation of hyaluronic acid (mAzo-HA) modified by azobenzene derivatives

[0101] (11) Preparation of tetra-o-methoxy substituted azobenzene (mAzo)

[0102] Dissolve 1g of granular 2,6-dimethoxyaniline in a mixed solution of 1.2mL of water and 1.5mL of 37wt% hydrochloric acid. After cooling to 3°C, slowly add 4mL of NaNO with a concentration of 1.8mol / L 2 solution and stirred for 20 minutes. At 3°C, slowly add the above mixed solution to the suspension formed by 1 g of 3,5-dimethoxyaniline and 40 mL of water, then add a 2 mol / L sodium bicarbonate solution to adjust the pH of the reaction solution to 8.5, and stir Overnight (about 12h). Use dichloromethane to extract the reacted solution, separate the liquid from the organic layer with a separatory funnel, concentrate the organic solution by rotar...

Embodiment 3

[0119] The preparation method steps of the near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair provided in this example are as follows:

[0120] (1) Preparation of hyaluronic acid (mAzo-HA) modified by azobenzene derivatives

[0121] (11) Preparation of tetra-o-methoxy substituted azobenzene (mAzo)

[0122] Dissolve 1g of granular 2,6-dimethoxyaniline in a mixed solution of 1.2mL of water and 1.5mL of 37wt% hydrochloric acid. After cooling to 4°C, slowly add 4mL of NaNO with a concentration of 1.8mol / L 2 solution and stirred for 20 minutes. At 4°C, slowly add the above mixed solution to the suspension formed by 1 g of 3,5-dimethoxyaniline and 40 mL of water, then add a 2 mol / L sodium bicarbonate solution to adjust the pH of the reaction solution to 8.5, and stir Overnight (about 12h). Use dichloromethane to extract the reacted solution, separate the liquid from the organic layer with a separatory funnel, concentrate the organic solution by rotar...

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Abstract

The invention discloses a near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and a preparation method thereof. The hydrogel is transparent hyaluronic acid modified with azobenzene derivatives and cyclodextrin derivatives. Glycolic acid is made of raw materials by cross-linking reaction at a mass ratio of 1:1. Azobenzene derivatives are tetra-o-methoxy substituted azobenzenes modified with long alkyl chains. Cyclodextrin derivatives are made of hexamethylenediamine Modified cyclodextrins. The hyaluronic acid modified by the azobenzene derivative and the hyaluronic acid modified by the cyclodextrin derivative are dissolved in proportion, the two solutions are mixed evenly, and the gel is formed by standing still or ultrasonically. The hydrogel is self-healing and injectable based on non-covalent cross-linked hydrogel, and can undergo partial gel-sol transition under the stimulation of near-infrared light, resulting in a cross-linked network density on the surface of the gel. The formation of a hydration layer based on the reduction of the near-infrared photoresponse and the formation of the hydration layer make it have potential significance in the field of cartilage repair.

Description

technical field [0001] The invention belongs to the field of biomedical materials and relates to hyaluronic acid hydrogel, in particular to a near-infrared responsive hyaluronic acid hydrogel for articular cartilage repair and a preparation method thereof. Background technique [0002] Joints are the functional connection points between bones in the skeletal system. In synovial joints, the bony end of the joint is covered with a layer of 1-7mm thick white transparent connective tissue—articular cartilage (AC), which is the weight-bearing tissue of the synovial joint, which can reduce the friction of the articular surface during repeated movements , has the characteristics of lubrication and wear resistance, and also has the function of reducing impact and absorbing shock. Degeneration or damage of articular cartilage caused by disease or trauma is relatively common in clinical practice. Due to the special nature of articular cartilage tissue, there are no blood vessels, lym...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08J3/075C08J3/24C08L5/08C08B37/08A61L27/20A61L27/50A61L27/52A61L27/54
CPCC08J3/075C08J3/24A61L27/52A61L27/50A61L27/20A61L27/54C08B37/0072A61L2430/06A61L2400/06A61L2300/412A61L2300/602C08J2305/08C08J2405/08C08L5/08C08L5/16
Inventor 范红松吴凯孙静卫丹吴肖阳马言哲
Owner SICHUAN UNIV
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