Hyaluronic acid cross-linked chondroitin sulfate compound and application thereof

A technology of chondroitin sulfate and sodium hyaluronate, which is applied in the directions of non-active ingredients medical preparations, medical preparations containing active ingredients, and drug combinations, can solve problems such as being easily enzymatically hydrolyzed, and achieve a suitable degree of cross-linking. , the effect of good biological activity

Active Publication Date: 2020-06-26
SHANDONG TOPSCI BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problem that chondroitin sulfate and heparanoid are easily hydrolyzed during use, the present invention provides a cross-linked chondroitin sulfate or heparan, the cross-linked compound has stable properties and is not easy to degrade

Method used

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  • Hyaluronic acid cross-linked chondroitin sulfate compound and application thereof
  • Hyaluronic acid cross-linked chondroitin sulfate compound and application thereof
  • Hyaluronic acid cross-linked chondroitin sulfate compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Synthesis of hyaluronic acid-chondroitin sulfate cross-linked product

[0039] (1) Dissolve 20g of sodium chloride and 5g of tetrabutylammonium bromide in 1000mL of distilled water for later use, weigh 20g of sodium hyaluronate with a molecular weight of 200kDa in a 2000mL reaction flask and dissolve it in the above distilled aqueous solution, then add 10g of EDC· After the HCl is completely dissolved, adjust the pH to 4.0 and react at room temperature for 3 hours, and check the pH every 15 minutes to keep it at 4.0;

[0040] (2) Weigh 20g of chondroitin sulfate and add it to the above reaction flask to dissolve, then add 10g of EDC·HCl to dissolve, adjust the pH to 4.0 and react at room temperature for 3h;

[0041] (3) Dilute the above solution to 10L for ultrafiltration, ultrafiltration until the solution is 1000mL, dilute the ultrafiltration again, and perform ultrafiltration three times to obtain 1000mL of effluent;

[0042] (4) Add 20g of sodium chloride...

Embodiment 2

[0043] Example 2 Synthesis of hyaluronic acid-heparan cross-linked product

[0044] (1) Dissolve 20g of sodium chloride and 5g of tetrabutylammonium bromide in 1000mL of distilled water for later use, weigh 20g of sodium hyaluronate with a molecular weight of 200kDa in a 2000mL reaction flask and dissolve it in the above distilled aqueous solution, then add 10g of EDC· After the HCl is completely dissolved, adjust the pH to 4.0 and react at room temperature for 3 hours, and check the pH every 15 minutes to keep it at 4.0;

[0045] (2) Weigh 20g of heparinoid and add it to the above reaction bottle to dissolve, then add 10g of EDC·HCl to dissolve, adjust the pH to 4.0 and react at room temperature for 3h;

[0046] (3) Dilute the above solution to 10L for ultrafiltration, ultrafiltration until the solution is 1000mL, dilute the ultrafiltration again, and perform ultrafiltration three times to obtain 1000mL of effluent;

[0047] (4) Add 20g of sodium chloride to the effluent to ...

Embodiment 3

[0048] Example 3 Detection of cross-linking degree of cross-linked chondroitin sulfate compounds

[0049] (1) Cross-linked chondroitin sulfate

[0050]Accurately weigh 5 g of cross-linked chondroitin sulfate prepared in Example 1, place in a 250 mL pressure-resistant bottle, transfer 20.00 mL of 0.5 mol / L sodium hydroxide standard solution with a pipette, and magnetically stir in a water bath at 50°C 30min to make it fully saponified, add 3 drops of phenolphthalein indicator, titrate with 0.25mol / L hydrochloric acid standard solution until colorless as the end point, measure in parallel three times, the volume of hydrochloric acid consumed is V 1 .

[0051] Follow the above steps, but do not add cross-linked chondroitin sulfate / sodium hyaluronate, conduct 3 blank experiments, and consume a volume of hydrochloric acid of V 2 .

[0052] Cross-linking degree x= .

[0053] (2) Cross-linked heparan

[0054] Accurately weigh 5 g of the cross-linked heparin prepared in Example...

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Abstract

The invention provides a preparation method of a cross-linked chondroitin sulfate compound. The method comprises the following steps: in the presence of a phase transfer catalyst, dissolving sodium hyaluronate and EDC.HCl (1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride) in water, regulating the pH value, and carrying out stirring reaction; then adding a chondroitin sulfate compound andEDC.HCl, adjusting the pH value to acidic, and carrying out stirring reaction; carrying out ultrafiltration and impurity removal on the solution to obtain effluent; and adjusting the pH value of the effluent, adding ethanol to obtain a precipitate, and washing and drying the precipitate to obtain the cross-linked chondroitin sulfate compound. The cross-linked chondroitin sulfate compound preparedby the invention is proper in cross-linking degree, has good biological activity, is stable in properties and not easy to degrade, can be used for preparing chondroitin sulfate ointment and heparinoidointment, and has anti-inflammatory and antibacterial effects.

Description

technical field [0001] The invention belongs to the field of raw material drug synthesis, and in particular relates to chondroitin sulfate or heparin-like cross-linked sodium hyaluronate and application thereof. Background technique [0002] Chondroitin sulfate, referred to as CS, is a kind of sulfated acidic mucopolysaccharide composed of repeating disaccharide units of glucuronic acid and N-acetylgalactosamine. Chondroitin sulfate exists in many tissues and organs of humans and animals, and is mostly distributed in different tissues such as cartilage, ligaments, tendons, and cornea. Has certain antioxidant and free radical scavenging effects. Heparin, a polysulfated chondroitin sulfate, has certain anti-inflammatory and antibacterial effects. [0003] The common chondroitin sulfate ointment and heparin-like ointment on the market are added with chondroitin sulfate and heparin-like to achieve anti-inflammatory, swelling and scar removal effects. However, chondroitin sulf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/24C08L5/08A61K47/36A61K31/737A61K31/727A61P29/00A61P31/00
CPCC08J3/246A61K47/36A61K31/737A61K31/727A61P29/00A61P31/00C08J2305/08C08J2405/08A61K2300/00
Inventor 邢仕杰朱伟伟张建勇张新庆刘英豪王咏梅尤加宇相茂功王新志申加秋王斌王勇
Owner SHANDONG TOPSCI BIO TECH
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