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Injectable modified hyaluronic acid and its preparation method and composition

A hyaluronic acid and modification technology, applied in the field of modified hyaluronic acid, can solve the problems of host poisoning and achieve the effect of simple and efficient method and mild reaction conditions

Active Publication Date: 2016-04-27
NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method requires the application of triggers and chemical cross-linking agents, which will inevitably cause toxicity to the host.

Method used

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  • Injectable modified hyaluronic acid and its preparation method and composition
  • Injectable modified hyaluronic acid and its preparation method and composition
  • Injectable modified hyaluronic acid and its preparation method and composition

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preparation example Construction

[0074] The preparation method of modified hyaluronic acid comprises the following steps:

[0075] 1) Dissolving hyaluronic acid in an aqueous solution, adding 1-amino-3,3-diethoxypropane ADEP and an optional amide reaction catalyst, reacting completely to obtain the reactant HA-ADEP and purifying;

[0076] 2) Dissolve the purified HA-ADEP, adjust the pH of the HA-ADEP solution to acidic with a non-oxidizing acid, complete the reaction, and purify to obtain modified HA, which is denoted as AHA.

[0077] The reaction formula is as follows:

[0078] .

[0079] The amount of ADEP added can be adjusted according to the substitution ratio. In order to speed up the reaction and facilitate the subsequent purification, the amount of ADEP added is generally added in excess.

[0080] The above-mentioned aqueous solution can be water, or various buffers, such as PBS solution, acetate buffer, TE buffer, HEPES buffer, etc.; HA and ADEP are dissolved in the aqueous solution, which can re...

Embodiment 1

[0085] Dissolve 250mg HA in 10ml of 0.1mol / l PBS, add 125mgEDC and 100mgNHS as amide reaction catalyst, stir evenly, then add 389mgADEP and let it stand to react overnight, dialyze to remove unreacted small molecules, dry to obtain purified reactant HA-ADEP ;

[0086] Dissolve HA-ADEP in water, add hydrochloric acid to adjust the pH of the solution to 1-3, let it stand for reaction to form aldehyde groups, after the reaction is complete, dialyze and purify, and dry to obtain modified HA, which is designated as AHA.

Embodiment 2

[0088] Dissolve 250 mg HA in 10 ml of 0.1 mol / l acetic acid, add 100 mg EDC and 100 mg N-hydroxysulfosuccinimide as amide reaction catalysts, stir evenly, then add 800 mg ADEP and let it stand for reaction overnight, dialyze to remove unreacted small molecules, dry Obtain purified reactant HA-ADEP;

[0089] Dissolve HA-ADEP in water, add hydrochloric acid to adjust the pH of the solution to 1-3, let it stand for reaction to form aldehyde groups, after the reaction is complete, dialyze and purify, and dry to obtain modified HA, which is designated as AHA.

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Abstract

The invention discloses an injectable modified hyaluronic acid, a preparation method and a composition thereof. The modified hyaluronic acid is partially substituted by the -OH in the -COOH in the hyaluronic acid structural unit, and the substitution rate is not less than 40%. The modified HA of the invention can directly react with chitosan to form a hydrogel without chemical cross-linking reaction and will not destroy the HA structure. Rheological experiments show that AHA-CS can be made into injections, and the formed hydrogel structure is relatively stable. Animal experiments have shown that AHA-CS hydrogel can accelerate wound healing, promote cell proliferation and promote keratinocyte migration. In hydrogel-treated wounds, histological examination also demonstrated that the hydrogel promoted granulation tissue and capillary formation. In gel-treated wounds, the expressions of angiogenic factors (VEGF-A), chemokines (SDF-1), extracellular matrix remodeling factors MMPs and other MRNAs were increased or upregulated. More significantly, newly formed hair follicles were found on the gel-treated wounds.

Description

technical field [0001] The invention mainly relates to a modified hyaluronic acid, and also relates to a preparation method and composition of the modified polymer. Background technique [0002] Hyaluronic acid is a high-molecular polymer. It is an advanced polysaccharide composed of units D-glucuronic acid and N-acetylglucosamine. D-glucuronic acid and N-acetylglucosamine are connected by β-1,3-glycosidic bonds, and disaccharide units are connected by β-1,4-glycosidic bonds. Disaccharide units can reach as many as 25,000. The molecular weight of hyaluronic acid in the body ranges from 50 to 20 million Daltons. Hyaluronic acid has special biological activity, and has the characteristics of non-toxicity, low immune response, high biocompatibility, biodegradability and human absorption, so it can also be used in eye surgery, intra-articular injection, wound Healing, surgical anti-sticking agent. Experiments have proved that hyaluronic acid can also be taken orally, and en...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08C08L5/08
Inventor 石敏邢梦秋鲁峰
Owner NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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