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Injectable modified hyaluronic acid, preparation method for same and composition

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

Active Publication Date: 2014-06-11
NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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, preparation method for same and composition
  • Injectable modified hyaluronic acid, preparation method for same and composition
  • Injectable modified hyaluronic acid, preparation method for same and composition

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preparation example Construction

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

[0075] 1) Dissolve hyaluronic acid in an aqueous solution, add 1-amino-3,3-diethoxypropane ADEP and an optional amide reaction catalyst, react completely to obtain the reactant HA-ADEP and purify it;

[0076] 2) Dissolve the purified HA-ADEP, use a non-oxidizing acid to adjust the pH of the HA-ADEP solution to acidic, 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 react mo...

Embodiment 1

[0085] Dissolve 250mg of HA in 10ml of 0.1mol / l PBS, add 125mg of EDC and 100mg of NHS as amide reaction catalysts, stir well, then add 389mg of ADEP and let it stand to react overnight, dialyze to remove unreacted small molecules, and dry to obtain a purified reaction substance 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 250mg of HA in 10ml of 0.1mol / l acetic acid, add 100mg of EDC and 100mg of N-hydroxysulfosuccinimide as amide reaction catalysts, stir well, then add 800mg of ADEP and let stand to react overnight, dialyze to remove unreacted Small molecules, dried to 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 injectable modified HA (hyaluronic acid), a preparation method for the same and a composition. -OH in -COOH in an HA structural unit is partially substituted by a group shown in the original document, and the substitution rate is not lower than 40 percent. The modified HA can be directly reacted with chitosan to form hydrogel without chemical cross-linking reaction and damage to the structure of the HA. Rheodynamic experiments show that AHA-CS can be prepared into injection, and the formed hydrogel is stable in structure. Animal experiments show that the AHA-CS hydrogel has the effects of accelerating the healing of wounds and promoting cell proliferation and keratinocyte migration. Histological detection for the wounds treated by the hydrogel also proves that the hydrogel has the effect of promoting the formation of granulation tissues and capillaries. The expression of MRNA (messenger ribose nucleic acid) such as a VEGF-A (vascular endothelial growth factor), an SDF-1 (stromal-derived factor-1) and MMPs (matrix metalloproteinases) at the wounds treated by the hydrogel is increased or upregulated. Significantly, new hair follicles are found on the wounds treated by the hydrogel.

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 Applications(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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