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Preparation method and application of hyaluronic acid modified by vitamin E succinate

A technology of hyaluronic acid and succinate, which is applied in the field of medicine, can solve problems such as unpublished reports, and achieve the effects of solving medication problems, increasing drug loading, and huge economic and social benefits

Inactive Publication Date: 2015-03-25
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, how to prepare vitamin E succinate-modified hyaluronic acid and realize the application in the preparation of antitumor drugs has not been published so far.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In concrete implementation, the present invention can be realized by the following steps:

[0018] (1) Amination of hyaluronic acid (HA): Dissolve 80-140mg of hyaluronic acid in 40-70ml of organic solvent or buffer, and dissolve 200-400mg of 1-ethyl-(3-dimethylaminopropyl ) carbodiimide, 100-200mg hydroxysuccinimide as an activator, react at room temperature for 10-200min to obtain a reaction solvent; mix alkylene diamine or dithioalkylene diamine with hyaluronic acid 6- Add the above reaction solvent at a molar ratio of 8:1, react at room temperature for 6-48 hours, then add acetone to precipitate, filter with suction to obtain the precipitate, add water to redissolve the precipitate, dialyze, and freeze-dry to obtain ammoniated hyaluronic acid;

[0019] (2) Dissolve 100-200mg vitamin E succinate in 40-70ml reaction solvent, add 200-400mg 1-ethyl-(3-dimethylaminopropyl) carbodiimide, 100-200mg hydroxysuccinate Imide is used as an activator, and the carboxyl group of v...

Embodiment 2

[0021] In specific implementation, the present invention can also be realized by the following methods:

[0022] (1) Amination of hyaluronic acid (HA): 110mg of hyaluronic acid was dissolved in 55ml of organic solvent or buffer, and 300mg of 1-ethyl-(3-dimethylaminopropyl)carbodiimide, 175 mg of hydroxysuccinimide is used as an activator, react at room temperature for 10 to 200 minutes to obtain a reaction solvent; add alkylene diamine or dithioalkylene diamine to the above reaction solvent in a molar ratio of 7.5:1 to hyaluronic acid , react at room temperature for 6-48 hours, then add acetone to precipitate, filter with suction to obtain the precipitate, add water to redissolve the precipitate, dialyze, and freeze-dry to obtain ammoniated hyaluronic acid;

[0023] (2) Dissolve 175mg vitamin E succinate in 55ml reaction solvent, use 300mg 1-ethyl-(3-dimethylaminopropyl) carbodiimide and 175mg hydroxysuccinimide as activator, vitamin The carboxyl group of E succinate and the ...

Embodiment 3

[0025] In specific implementation, the present invention can also be realized by the following methods:

[0026] (1) Dissolve 100 mg of hyaluronic acid, 498 mg of 1-ethyl-(3-dimethylaminopropyl) carbodiimide, and 300 mg of hydroxysuccinimide in 10 ml of formamide, and stir at room temperature for 30 min. The above reaction solution was slowly dropped into a 0.5M ethylenediamine formamide solution, added dropwise for 1 h under ice-bath conditions, and raised to room temperature for 3 h of reaction. After the reaction, add acetone, precipitate, filter with suction, add water to redissolve the precipitate, dialyze in water for 2 days, and freeze-dry to obtain hyaluronic acid (HA-EN) ammoniated with ethylenediamine;

[0027] (2) Dissolve 50 mg of vitamin E succinate in 30 ml of dimethylformamide, add 60 mg of 1-ethyl-(3-dimethylaminopropyl) carbodiimide and 35 mg of hydroxysuccinimide, React at room temperature for 15 minutes to form a reaction solution. Add 20 mg of hyaluronic a...

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PUM

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Abstract

The invention relates to a preparation method and application of hyaluronic acid modified by vitamin E succinate and is capable of effectively solving the problems of preparation of hyaluronic acid modified by vitamin E succinate and the application in antitumor drugs. The preparation method comprises the following steps: with alkylidene diamine or dithio alkylidene diamine as a linking arm, hyaluronic acid is covalently linked to vitamin E succinate according to the weight ratio of 1:(1-100) so as to form a nano-micelle in a water medium, wherein hyaluronic acid is low-molecular-weight hyaluronic acid with the molecular weight no less than 600 daltons and no larger than 400kd; the linking arm is the alkylidene diamine or the dithio alkylidene diamine with the amount of carbon atoms being 2-12, and a disulfide bond in the dithio alkylidene diamine has the oxidation-reduction sensitivity in vivo and is capable of releasing the antitumor drugs in a targeting mode in tumor cells. With HA as a skeleton, hyaluronic acid modified by vitamin E succinate is high in drug loading capacity and easy in releasing of the drugs, is effectively used for preparing the antitumor drugs, is capable of solving the problem of medication for treating tumors and is an innovation of the drugs for treating the tumors.

Description

technical field [0001] The invention relates to medicine, in particular to a preparation method and application of vitamin E succinate modified hyaluronic acid using vitamin E succinate modified hyaluronic acid as a drug carrier. Background technique [0002] Tumor is a major disease that threatens human health. Tumor chemotherapy has become the most effective and potential way to treat malignant tumors, and it is also the main method commonly used in clinical treatment of cancer. In recent years, with the continuous advent of chemotherapy drugs, the rehabilitation level of clinical tumor treatment has been greatly improved. However, there are many problems that the effect of tumor chemotherapy is not ideal, and the drug resistance of tumor cells seriously affects the clinical chemotherapy effect of drugs. According to the American Cancer Society estimates, more than 90% of cancer patients died of different degrees of tumor cell drug resistance. Therefore, it is imperative...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/36A61K47/22A61P35/00
Inventor 侯琳任俊晓张振中冯倩华单晓宁王亚婷杨晓敏石宇洋
Owner ZHENGZHOU UNIV
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