Hyaluronic acid-glucosamine grafted copolymer, and preparation method and application thereof

A technology of glucosamine and graft copolymers, applied in the field of hyaluronic acid modification, which can solve the problems of poor stability, sensitivity to free radicals and hyaluronidase, and easy degradation

Pending Publication Date: 2020-10-02
SHANDONG BLOOMAGE HYINC BIOPHARM CORP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] As we all know, hyaluronic acid has good biocompatibility and biodegradability, and is an excellent filler, but its stability is slightly poor, sensitive to free radicals and hyaluronidase in the human body, and prone to degradation

Method used

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  • Hyaluronic acid-glucosamine grafted copolymer, and preparation method and application thereof
  • Hyaluronic acid-glucosamine grafted copolymer, and preparation method and application thereof
  • Hyaluronic acid-glucosamine grafted copolymer, and preparation method and application thereof

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preparation example Construction

[0044] The invention provides a kind of preparation method of hyaluronic acid-glucosamine graft copolymer, it comprises the following steps:

[0045] mixing the condensing agent, glucosamine or its salt and water to obtain a mixed solution;

[0046] The pH value of the mixed solution is adjusted, and then hyaluronic acid or its salt is added for amidation reaction to obtain a hyaluronic acid-glucosamine graft copolymer.

[0047] For the condensing agent, the present invention has no limitation, as long as the carboxyl group of hyaluronic acid or its salt can be amidated with the amino group of glucosamine or its salt, for example, the use of carbodiimides and succinyl A composite condensing agent composed of imine substances, or a composite condensing agent composed of carbodiimide substances and benzotriazole substances, or a composite condensing agent composed of carbodiimide substances, benzotriazole substances and succinyl A composite condensing agent composed of amine su...

Embodiment 1

[0102] (1) At room temperature, add 4.79g of EDC, 2.88g of NHS and 13.86g of glucosamine sulfate to 100ml of purified water in sequence, and completely dissolve to obtain a mixed solution;

[0103](2) Use NaOH solution to adjust the pH value of the mixed solution to 9.0, then add 10g of hyaluronic acid (1500kDa) to the above solution while stirring, disperse evenly, put it at 4°C to activate for 10-30min, then take it out and place it React at room temperature for 4 hours. After the reaction is completed, add 200ml of purified water to dilute the reaction solution, then add 2.5 times the volume of ethanol for the dilution to precipitate, adjust the pH value of the precipitate suspension to 7.0 with hydrochloric acid, let it stand for a while, discard The supernatant was removed, the precipitate was repeatedly washed with ethanol and dehydrated 3 times, and finally the liquid was removed by suction filtration to obtain a wet powder, which was placed at 40°C for vacuum drying to ...

Embodiment 2

[0112] (1) At room temperature, add 9.58g of EDC, 5.75g of NHS and 13.86g of glucosamine sulfate to 100ml of purified water in sequence, and completely dissolve to obtain a mixed solution;

[0113] (2) Use NaOH solution to adjust the pH value of the mixed solution to 8.0, then add 10g of hyaluronic acid (900kDa) to the above solution while stirring, disperse evenly, put it at 4°C for 10-30min, and then take it out and place it React at room temperature for 8 hours. After the reaction is completed, add 200ml of purified water to dilute the reaction solution, and then add 2.5 times the volume of ethanol to precipitate the diluted solution. Use hydrochloric acid to adjust the pH value of the precipitated suspension to 7.0. After standing for a period of time, discard The supernatant and the precipitate were repeatedly washed with ethanol and dehydrated 3 times, and finally the liquid was removed by suction filtration to obtain a wet powder. The wet powder was placed in 40°C for va...

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Abstract

The invention discloses a hyaluronic acid-glucosamine grafted copolymer, and a preparation method and application thereof. The preparation method of the hyaluronic acid-glucosamine grafted copolymer comprises the following steps: mixing a condensing agent, glucosamine or salt thereof and water to obtain a mixed solution; adjusting the pH value of the mixed solution, then adding hyaluronic acid orsalt thereof, and performing an amidation reaction to obtain the hyaluronic acid-glucosamine grafted copolymer. The preparation method is simple and efficient; the method is performed in an aqueous solution to avoid environmental protection pressure caused by using an organic solvent; reaction conditions are mild, so long chains and molecular structures of hyaluronic acid or salt thereof in a reaction system cannot be damaged, and high molecular weight can be maintained; and through mediation of the condensing agent, hyaluronic acid and glucosamine are connected through a stable covalent bond,so the obtained hyaluronic acid-glucosamine grafted copolymer is injected into an articular cavity to directly recover the viscoelasticity of synovial fluid, and the hyaluronic acid-glucosamine grafted copolymer has the effects of lubricating and nourishing joints and has slow absorptivity.

Description

technical field [0001] The invention relates to the technical field of hyaluronic acid modification, in particular to a hyaluronic acid-glucosamine graft copolymer, a preparation method and an application thereof. Background technique [0002] Osteoarthritis is a relatively common joint disease, which is more harmful to patients. At present, more than half of the elderly in China over the age of 60 suffer from osteoarthritis. At the same time, osteoarthritis due to inappropriate exercise and trauma in young people is becoming more common. The disability rate of osteoarthritis is as high as 53%. Pain is the most common symptom of osteoarthritis. The purpose of osteoarthritis treatment is to relieve pain, delay disease progression, correct deformity, improve or restore joint function, and improve the quality of life of patients. [0003] Osteoarthritis treatment is divided into physical therapy, drug therapy and surgery. Among them, intra-articular drug injection therapy i...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K47/55A61K31/728A61K31/7008A61P19/00
CPCC08B37/0072A61K47/55A61K31/728A61K31/7008A61K9/0019A61P19/00A61K2300/00
Inventor 王冠凤石艳丽王成山李晓天周雪李梦娇郭学平
Owner SHANDONG BLOOMAGE HYINC BIOPHARM CORP LTD
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