Hyaluronic acid vitamin E derivative and preparation and application

A technology of hyaluronic acid and sodium hyaluronate, applied in the direction of liposome delivery, can solve the problems of biocompatibility, biotoxicity, drug-carrying system limitation, etc., and achieve the effect of excellent biocompatibility and biodegradability

Inactive Publication Date: 2015-09-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current micellar drug delivery systems are non-biologically active materials, which have problems such as biocompatibility and biotoxicity, and have many limitations as a drug delivery system.

Method used

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  • Hyaluronic acid vitamin E derivative and preparation and application
  • Hyaluronic acid vitamin E derivative and preparation and application
  • Hyaluronic acid vitamin E derivative and preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of hyaluronic acid and vitamin E derivatives

[0037] Weigh 0.5g vitamin E succinate (VES), 0.45g 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), 0.1g N-hydroxysulfosuccinimide (NHS) into a 50ml single-necked flask, add 25ml dimethyl sulfoxide (DMSO), stir and dissolve at room temperature for 60min. Another 0.2 g of hexamethylenediamine was weighed, dissolved in 10 ml of DMSO, slowly added dropwise to the reaction solution, stirred at room temperature for more than 8 hours, and the reaction solution A was obtained.

[0038] Weigh 0.38g sodium hyaluronate (HA-Na) with a molecular weight of about 6700 (n+m=17), 0.45g 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC ), 0.1g perimide (NHS) into a 100ml single-necked flask, add 60ml of water and ethanol mixed solution, stir and dissolve at room temperature for 60min, slowly add reaction solution A dropwise, and stir at room temperature for 4h. The reaction solution was dialyze...

Embodiment 2

[0064] (1) Weigh 0.5g vitamin E succinate (VES), 0.45g 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), 0.1g N-hydroxysulfosuccinate Put imide (NHS) into a 50ml single-necked flask, add 25ml dimethyl sulfoxide (DMSO), stir and dissolve at room temperature for 60min. Another 0.2g of cystamine was weighed, dissolved in 10ml of DMSO, slowly added dropwise to the reaction solution, and stirred at room temperature for more than 8 hours to obtain the reaction solution A.

[0065]Weigh 0.38g sodium hyaluronate (HA-Na) with a molecular weight of about 6700 (n+m=17), 0.45g 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC ), 0.1g perimide (NHS) into a 100ml single-necked flask, add 60ml of water and ethanol mixed solution, stir and dissolve at room temperature for 60min, slowly add reaction solution A dropwise, and stir at room temperature for 8h. The reaction solution was dialyzed in deionized water for 3-4 days to remove the catalyst and unreacted monom...

Embodiment 3

[0073] (1) Weigh 0.5g vitamin E succinate (VES), 0.45g 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), 0.1g N-hydroxysulfosuccinate Put the imide (NHS) into a 50ml single-necked flask, add 25ml dimethyl sulfoxide (DMSO), stir and dissolve at room temperature for 60min. Another 0.2 g of 3-aminopropanol was weighed, dissolved in 10 ml of DMSO, slowly added dropwise to the reaction solution, stirred at room temperature for more than 8 hours, and the reaction solution A was obtained.

[0074] Weigh 0.38g sodium hyaluronate (HA-Na) with a molecular weight of about 6700 (n+m=17), 0.45g 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC ), 0.1g 4-dimethylaminopyridine (DMAP) into a 100ml single-necked flask, add 60ml of water and ethanol mixed solution, stir and dissolve at room temperature for 60min, slowly add reaction solution A dropwise, and stir at room temperature for 8h. The reaction solution was dialyzed in deionized water for 3-4 days to remove...

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Abstract

The invention provides a hyaluronic acid vitamin E derivative. According to the hyaluronic acid vitamin E derivative, biological material hyaluronic acid and vitamin E succinic acid ester are taken as raw materials to form micelles in a water medium. The provided micelles can be self-assembled in an aqueous solution to form a micelle drug delivery system, the carrying of non-water-soluble drugs is achieved, and then the drug targeting function is achieved. According to the hyaluronic acid vitamin E derivative, the natural macromolecule hyaluronic acid is taken as the raw material, the non-toxic effect, moisture preservation and excellent biocompatibility and biodegradability are achieved. The hydrophobic vitamin E succinic acid ester is connected to a hyaluronic acid main chain, and the hyaluronic acid vitamin E derivative is formed. A preparation method is reasonable in design and easy in method, the reaction is easy to conduct, and the obtained micelles are structured in form and small in particle size. The hyaluronic acid vitamin E micelles are excellent in biocompatibility, hydrophily and biodegradability, high in hydrophobic drug warping capacity and specific binding capacity with CD44 receptors and capable of serving as excellent targeted drug delivery carriers. The structure formula of the hyaluronic acid vitamin E derivative is shown (please see the structure formula in the instruction).

Description

technical field [0001] The invention belongs to the technical field of high molecular polymers and pharmaceutical preparations. The invention relates to a hyaluronic acid vitamin E derivative, a synthesis method and a pharmaceutical use thereof. [0002] Preparation and application of micelles, connecting vitamin E succinate to the main chain of hyaluronic acid to form hyaluronic acid vitamin E derivatives, which can self-assemble in aqueous solution to form micellar drug delivery systems, Background technique [0003] Micelles are colloid-sized aggregate particle particles formed by the automatic association of molecules or ions of amphiphilic substances in a solution when the concentration of amphiphilic substances reaches a certain critical value (ie, the critical micelle concentration CMC) and exceeds this value. There is a state of equilibrium between particles and ions. As a drug carrier, micelles have many excellent properties, such as high stability in vivo and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C08J3/02C08L5/08A61K9/127A61K47/36
Inventor 游剑张汉波
Owner ZHEJIANG UNIV
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