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Novel carboxymethyl chitosan derivative, and preparation method and application thereof

A technology of carboxymethyl chitosan and its derivatives, which can be used in pharmaceutical formulations, medical preparations with non-active ingredients, and medical preparations containing active ingredients, etc. Drug insoluble and other problems, to achieve the effect of uniform shape, uniform size, uniform particle size dispersion

Active Publication Date: 2017-12-22
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Generally, anticancer drugs have disadvantages such as insoluble, non-targeting, large side effects, and easy to cause drug resistance. A series of nanocarriers loaded with anticancer drugs have been developed, which can effectively improve the solubility and stability of insoluble drugs. , and through the unique EPR (Enhanced permeability and retention effect, EPR) effect of tumor tissue to achieve targeting, reduce toxic side effects and drug resistance, it has become a new research method for cancer drug delivery

Method used

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  • Novel carboxymethyl chitosan derivative, and preparation method and application thereof
  • Novel carboxymethyl chitosan derivative, and preparation method and application thereof
  • Novel carboxymethyl chitosan derivative, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: the preparation method of carboxymethyl chitosan-vitamin E succinate:

[0032] Weigh 0.66g of O-carboxymethyl chitosan (O-CMCTS) and dissolve it in 60mL of deionized water to obtain an aqueous solution of carboxymethyl chitosan; weigh 3.16g of vitamin E succinate (VES) and dissolve it in 70mL In dimethylformamide (DMF), after dissolving, add 1.16g EDC and 0.69g NHS, after catalyzing 30min, the carboxymethyl chitosan aqueous solution of above-mentioned preparation is dripped in this reaction solution, after dropwise adding, At room temperature, the reaction was mechanically stirred at a speed of 200 rpm for 48 h. After the reaction was completed, the reaction solution was precipitated with 5 times the volume (650 mL) of absolute ethanol, and after suction filtration, the precipitate was washed three times with an appropriate amount of absolute ethanol, then dissolved in deionized water, dialyzed for three days, and freeze-dried to obtain carboxymethyl Chit...

Embodiment 2

[0033] Embodiment 2: the preparation method of carboxymethyl chitosan-vitamin E succinate:

[0034] Weigh 0.66g of O-carboxymethyl chitosan (O-CMCTS) and dissolve it in 60mL deionized water to obtain an aqueous solution of carboxymethyl chitosan; weigh 1.59g vitamin E succinate (VES) and dissolve it in 70mL In dimethylformamide (DMF), after dissolving, add 0.58g EDC and 0.35g NHS to catalyze for 30min, drop the carboxymethyl chitosan aqueous solution prepared above into the reaction solution drop by drop, Under these conditions, the reaction was mechanically stirred at a speed of 200 rpm for 48 h. After the reaction was completed, the reaction solution was precipitated with 5 times the volume (650 mL) of absolute ethanol, and after suction filtration, the precipitate was washed three times with an appropriate amount of absolute ethanol, then dissolved in deionized water, dialyzed for 3 days, and freeze-dried to obtain carboxymethyl Chitosan-Vitamin E Succinate. According to ...

Embodiment 3

[0035] Embodiment 3: the preparation method of carboxymethyl chitosan-vitamin E succinate:

[0036]Weigh 0.66g of O-carboxymethyl chitosan (O-CMCTS) and dissolve it in 60mL of deionized water to obtain an aqueous solution of carboxymethyl chitosan; weigh 1.19g of vitamin E succinate (VES) and dissolve it in 70mL In dimethylformamide (DMF), after dissolving, add 0.47g EDC and 0.26g NHS to catalyze for 30min, then drop the carboxymethyl chitosan aqueous solution prepared above into the reaction solution drop by drop, Under these conditions, the reaction was mechanically stirred at a speed of 200 rpm for 48 h. After the reaction was completed, the reaction solution was precipitated with 5 times the volume (650 mL) of absolute ethanol, and after suction filtration, the precipitate was washed three times with an appropriate amount of absolute ethanol, then dissolved in deionized water, dialyzed for 3 days, and freeze-dried to obtain carboxymethyl Chitosan-Vitamin E Succinate. Acc...

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Abstract

The invention provides a novel carboxymethyl chitosan derivative and a preparation method and application thereof. The preparation method comprises the following steps: firstly synthesizing a novel material O-carboxymethyl chitosan-vitamin E succinate (O-CMCTS-VES), and grafting some of free amino groups of the O-carboxymethyl chitosan with the vitamin E succinate, wherein covalent bonds are formed between the O-carboxymethyl chitosan and the vitamin E succinate in a way of forming amide bonds and the degree of VES substitution is 3-5%. The O-CMCTS-VES is self-assembled in water to form nanoparticles, and the nanoparticles have the particle size of 100-200 nanometers, the Zeta potential of -29mV, the highest model drug doxorubicin (DOX) encapsulating rate of 74.5% and the highest drug loading capacity of 13%. The drug-loaded nanoparticles prepared by using the preparation method provided by the invention have the particle size of 100-200 nanometers, have uniform shapes and sizes and are uniformly dispersed, which indicate that the O-CMCTS-VES / DOX prepared by using the preparation method provided by the invention can effectively coat a hydrophobic drug and is a good drug carrier.

Description

technical field [0001] The invention relates to a carboxymethyl chitosan derivative, which belongs to the technical field of marine chemical engineering. Background technique [0002] Amphiphilic polymeric micelles (Apm) are composed of two parts: one part is a hydrophilic and oleophobic polar polymer, called a hydrophilic group, such as chitosan derivatives, etc.; the other part is It is a hydrophobic and lipophilic non-polar group, called a hydrophobic group, such as cholesterol, palmitic acid, etc. This kind of amphiphilic polymer micelles can form micelles with "hydrophobic core-hydrophilic shell" through the principle of self-assembly in aqueous solution, that is, in aqueous solution, hydrophobic groups are repelled and associate with each other to form a core, while hydrophilic groups The clusters are attracted by water and arranged on the outside to form a hydrophilic shell. By controlling the molecular weight of the materials used and the amount of hydrophobic grou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K31/704A61K9/14A61K47/36A61K47/22
CPCA61K9/145A61K9/146A61K31/704C08B37/003
Inventor 常菁古军祥陈晓彤张海斌韩宝芹刘万顺
Owner OCEAN UNIV OF CHINA
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