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Cross-linkable amphiphilic natural polysaccharide and application thereof

A natural polysaccharide and amphiphilic technology, which is applied in the direction of non-active ingredient medical preparations, medical preparations containing active ingredients, aerosol delivery, etc., can solve the problems of poor stability and achieve efficient delivery

Active Publication Date: 2018-06-01
CHINA PHARM UNIV
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Technical problem to be solved: The purpose of the present invention is to solve the technical problem that the natural polysaccharide macromolecules modified by hydrophobic groups have poor stability when loaded with water-soluble protein drugs, and provide a cross-linked polysaccharide that uses double bonds and hydrophobic chains for double modification. Amphiphilic natural polysaccharides can self-assemble into nanogels in aqueous solution and can be cross-linked for efficient delivery of protein drugs

Method used

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  • Cross-linkable amphiphilic natural polysaccharide and application thereof
  • Cross-linkable amphiphilic natural polysaccharide and application thereof
  • Cross-linkable amphiphilic natural polysaccharide and application thereof

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preparation example Construction

[0040] The blank nanogel was prepared by probe ultrasonic method. The cross-linkable amphiphilic hyaluronic acid was dissolved in the aqueous solution, and the probe was ultrasonicated for 10 minutes in an ice bath with an ultrasonic intensity of 240W. The loading of protein is carried in the presence of a small amount of organic solvent, including methanol, ethanol, dimethyl sulfoxide, etc., preferably dimethyl sulfoxide. In the present invention, multiple proteins are used to investigate the efficiency of protein loading, and the mass ratio of nanogel and protein is 1:0.2 to 1:1. Taking 1:0.2 as an example, the encapsulation rate of various model proteins is as high as 85-99%. .

[0041] It has been reported in the literature that the modification of hyaluronic acid with cholesterol alone can be used for protein loading (T.Nakai, T.Hirakura, Y.Sakurai, T.Shimoboji, M.Ishigai, K.Akiyoshi. Injectable hydrogel for sustained protein release by salt- induced association of hyal...

Embodiment 1

[0043] 1. Synthesis of hyaluronic acid double-modified with methacrylic acid and cholesteryl hexamethylenediamine

[0044] The first step, the preparation of cholesteryl hexamethylenediamine:

[0045] Cholesterol chloroformate dissolved in dichloromethane was added dropwise to 1,6-hexanediamine dissolved in dichloromethane, the molar ratio of 1,6-hexanediamine to cholesterol chloroformate was 10:1. After the dropwise addition, react at room temperature for 2 h. After the reacted product was washed with water, the organic phase was collected and dried with anhydrous sodium sulfate for half an hour, filtered with suction to remove anhydrous sodium sulfate, and a light yellow solid was obtained as a crude product after rotary evaporation. The purified product was purified by chromatographic column to obtain cholesterol hexamethylenediamine (product 1).

[0046]

[0047] The second step, the synthesis of methacrylic acid modified hyaluronic acid:

[0048] Add 1.6mL 2-methacr...

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Abstract

The invention discloses a cross-linkable amphiphilic natural polysaccharide and application thereof. Specifically, in particular, a double-bond and a hydrophobic chain are employed for dual modification of a natural polysaccharide polymer to obtain cross-linkable amphiphilic natural polysaccharide, and the cross-linkable amphiphilic natural polysaccharide is applied to loading and delivery of protein drugs. The amphiphilic natural polysaccharide provided by the invention can self-assemble into nanogel with protein loading capacity in an aqueous solution, and then an initiator is employed to activate the double-bond modifying natural polysaccharide to generate a free radical, thus triggering mutual crosslinking of the double-bond to form a new covalent bond, and the stable action force of the covalent bond is utilized to obtain the preparation so as to achieve efficient delivery of protein drugs.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, in particular to a cross-linkable amphiphilic natural polysaccharide double-modified with double bonds and hydrophobic chains and its application in delivering protein drugs. Background technique [0002] In the past 20 to 30 years, the development of molecular biology and genetic engineering has promoted the production and large-scale production of therapeutic proteins and peptides. Many protein drugs, such as cytokines, growth factors, monoclonal antibodies, low-molecular-weight antibodies, and skeleton proteins, are partly under clinical research, and partly have been put into the market. Compared with small molecule drugs, protein drugs have the characteristics of high activity, strong specificity, low toxicity, and clear biological functions. However, protein drugs usually have a complex three-dimensional structure. Regardless of the route of administration, there are de...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K9/06A61K47/36A61K38/46
CPCA61K9/06A61K38/465A61K47/36C08B37/0072C12Y301/21001
Inventor 莫然朱秋文陈晓杰章颖
Owner CHINA PHARM UNIV
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