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Cysteamine modified sulfhydryl hyaluronic acid couplet, preparation and application thereof

A technology of hyaluronic acid and cysteamine hydrochloride is applied in biochemical equipment and methods, medical preparations with non-active ingredients, microorganisms, etc., and can solve the problems of low content of disulfide bonds and poor in-situ gelation. , to achieve the effect of increasing local concentration, improving mechanical properties and improving bioavailability

Inactive Publication Date: 2009-02-18
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hyaluronic acid-cysteine ​​ethyl ester conjugates have low disulfide bond content and poor in situ gelation

Method used

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  • Cysteamine modified sulfhydryl hyaluronic acid couplet, preparation and application thereof
  • Cysteamine modified sulfhydryl hyaluronic acid couplet, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 200mg molecular weight is 5×10 5 Sodium hyaluronate of Da was dissolved in 50ml deionized water to obtain a 0.4% hyaluronic acid solution, and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide was added with a final concentration of 0.96% respectively Hydrochloride (EDAC) and 0.58% N-hydroxysuccinimide (NHS), adjusted to pH 5.5 after dissolving, stirred for 45 minutes; 400 mg of semicarpine hydrochloride was added to adjust the pH of the reaction solution to 4.75, and reacted in the dark for 5 hours. After the reaction, the reaction mixture was placed in a dialysis bag with a cut-off molecular weight of 3500Da, dialyzed with HCl solution (pH 4), 1% NaCl-containing HCl solution (pH 4), HCl solution (pH 4) successively, freeze-dried to obtain cysteamine Modified thiolated hyaluronic acid conjugates.

Embodiment 2

[0033] The molecular weight of 300mg is 1.98×10 4 Da sodium hyaluronate was dissolved in 50ml of deionized water to obtain a 0.6% hyaluronic acid solution, and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide was added with a final concentration of 0.19% respectively Hydrochloride (EDAC) and 0.12% N-hydroxysuccinimide (NHS) were dissolved, adjusted to pH 5, and stirred for 30 minutes; 300 mg of sphenamine hydrochloride was added to adjust the pH of the reaction solution to 3, and the reaction was protected from light for 4 hours. After the reaction, the reaction mixture was placed in a dialysis bag with a cut-off molecular weight of 3500Da, dialyzed with HCl solution (pH 4), 1% NaCl-containing HCl solution (pH 4), HCl solution (pH 4) successively, freeze-dried to obtain cysteamine Modified thiolated hyaluronic acid conjugates.

Embodiment 3

[0035] The molecular weight of 400mg is 1×10 5 Sodium hyaluronate of Da was dissolved in 50ml deionized water to obtain a 0.8% hyaluronic acid solution, and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide was added with a final concentration of 0.48% respectively Hydrochloride (EDAC) and 0.29% N-hydroxysuccinimide (NHS) were dissolved, adjusted to pH 5.5, and stirred for 40 minutes; 200 mg of sphenamine hydrochloride was added to adjust the pH of the reaction solution to 4, and reacted in the dark for 5 hours. After the reaction, the reaction mixture was placed in a dialysis bag with a cut-off molecular weight of 3500Da, dialyzed with HCl solution (pH 4), 1% NaCl-containing HCl solution (pH 4), HCl solution (pH 4) successively, freeze-dried to obtain cysteamine Modified thiolated hyaluronic acid conjugates.

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Abstract

The invention belongs to the technical field of high polymer materials, in particular to a thiolated hyaluronic acid conjugate modified by cysteamine, a preparation method and an application thereof. The method comprises the steps of adding 1-ethyl-3-(3-dimethylamino propyl)-carbodiimide (EDAC) and N-hydroxysuccinimide (NHS) in the hyaluronic acid solution to activate the carboxyl of the hyaluronic acid solution, adding cysteamine hydrochloride to make the amino of cysteamine hydrochloride and the carboxyl of hyaluronic acid to form amido link, regulating the proportions of each material and reaction conditions to obtain the thiolated hyaluronic acid conjugates with different sulfhdryl contents. The invention widens the application range of the thiolated reaction. The adhesive properties of the mucosa and the biocompatibility of the conjugate are good. The invention has strong in-situ gel property and supplies good bio-adhesive materials for non-injected preparations, tissue engineering and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a cysteamine-modified mercaptolated hyaluronic acid conjugate and a preparation method and application thereof. Background technique [0002] Thiomer is a product obtained by modifying the side chain of a kind of hydrophilic polymer with thiol compound, and it is a new type of mucoadhesive material. Under physiological conditions, it can form a disulfide bond with the cysteine-rich region in the mucous layer glycoprotein, and bind tightly to the mucosa with a covalent bond, prolong the residence time of the drug in the body, increase the local concentration of the drug, and promote the release of the drug. absorb. In addition, thiolated polymers have in-situ gel properties, and disulfide bonds can be formed in their molecules, resulting in changes in rheological properties. At present, cationic thiolated polymers such as chitosan-cysteine, chitosan-thiogly...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K47/36A61L27/20C12N5/08C12N5/07
Inventor 印春华丁洁英唐翠
Owner FUDAN UNIV
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