Application of fluorine-containing compound modified chitosan as drug carrier and preparation method of fluorine-containing compound modified chitosan

A chitosan derivative and chitosan technology are applied in medical preparations containing active ingredients, medical preparations with inactive ingredients, drug combinations, etc., and can solve problems such as limited clinical application, mucosal and epithelial damage, etc.

Pending Publication Date: 2020-10-30
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although chitosan can significantly improve the bioavailability of infused drugs, high concentrations of chitosan may cause severe mucosal and epithelial damage, which limits its clinical application as a drug carrier.

Method used

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  • Application of fluorine-containing compound modified chitosan as drug carrier and preparation method of fluorine-containing compound modified chitosan
  • Application of fluorine-containing compound modified chitosan as drug carrier and preparation method of fluorine-containing compound modified chitosan
  • Application of fluorine-containing compound modified chitosan as drug carrier and preparation method of fluorine-containing compound modified chitosan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Embodiment 1: prepare the chitosan (deacetylation degree≧95%, viscosity 100-200mpa.s) of the different modification degree of 3-fluorobenzoic acid, wherein the feeding molar ratio of 3-fluorobenzoic acid and N-glucosamine unit is respectively 1:1.1, 1:2.2, 1:4.4, 1:8.8.

[0106] Synthetic method: (1) preparation of chitosan acetic acid aqueous solution: take by weighing 200mg fully dried chitosan and add in 10ml 1% acetic acid aqueous solution, also can adopt hydrochloric acid aqueous solution certainly, stir 30min to fully dissolve, then slowly add dropwise 1.6ml0. 5M sodium hydroxide, stirred until the solution was clear and the pH was around 6.5. From the point of view of alkalization solution, sodium hydroxide can be replaced by alkalis such as ammonia water and triethylamine, but the by-product of using sodium hydroxide is sodium chloride from the perspective of product technology, which is more suitable for industrialization. Prepare 4 parts of chitosan acetic ac...

Embodiment 2

[0108] Example 2: Preparation of chitosan with different degrees of modification of heptafluorobutyric acid (deacetylation degree≧95%, viscosity 100-200mpa.s), wherein the molar ratios of perfluoroheptanoic acid and N-glucosamine units are respectively 1: 1.1, 1:2.2, 1:4.4, 1:8.8.

[0109] Synthesis method: (1) Preparation of chitosan acetic acid aqueous solution: take 200 mg of fully dried chitosan and add it to 10 ml of 1% acetic acid aqueous solution, stir for 30 min to fully dissolve, then slowly add 1.6 ml of 0.5 M sodium hydroxide dropwise, stir Until the solution is clear and the pH is around 6.5. Prepare 4 parts of chitosan acetic acid aqueous solution in this way. (2) Activation of heptafluorobutyric acid: Weigh 7.6mg, 15mg, 30mg, and 61mg of heptafluorobutyric acid respectively, dissolve them in an appropriate amount of anhydrous dimethyl sulfoxide, add the reaction amount of EDC in turn, and stir in NHS in the dark 1h. (3) Preparation of heptafluorobutyric acid c...

Embodiment 3

[0111] Example 3: Preparation of chitosan with different degrees of modification of perfluoroheptanoic acid (deacetylation degree≧95%, viscosity 100-200mpa.s), wherein the molar ratios of perfluoroheptanoic acid and N-glucosamine units are respectively 1: 1.1, 1:2.2, 1:4.4, 1:8.8.

[0112] Synthesis method: (1) Preparation of chitosan acetic acid aqueous solution: take 200 mg of fully dried chitosan and add it to 10 ml of 1% acetic acid aqueous solution, stir for 30 min to fully dissolve, then slowly add 1.6 ml of 0.5 M sodium hydroxide dropwise, stir Until the solution is clear and the pH is around 6.5. Prepare 4 parts of chitosan acetic acid aqueous solution in this way. (2) Activation of perfluoroheptanoic acid (13fluoroheptanoic acid): Weigh 13mg, 26mg, 51.5mg, and 103mg of perfluoroheptanoic acid respectively, dissolve them in an appropriate amount of anhydrous dimethyl sulfoxide, and add appropriate amount of EDC in turn , NHS in the dark and stirred for 1h. (3) Prepa...

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Abstract

The invention discloses a fluorinated modified chitosan derivative used as a drug carrier. The structure is shown in the specification. The fluorine-containing compound is covalently connected to a chitosan main chain; the molecular weight of the chitosan ranges from 5000 to 5000000, wherein the fluorine-containing compound is a fluorine-containing aliphatic chain represented by the following chemical formula (I) or an aromatic ring functional group represented by the following chemical formula (II), and R1 is halogen (fluorine, chlorine, bromine and iodine), halogen-substituted alkane, cycloalkane, aldehyde group, carboxyl group, double bond, acetylene bond, hydroxyl group, sulfonyl chloride, sulfonic acid bond or sulfydryl and other active groups capable of reacting with primary amino group. The invention aims to provide a novel drug carrier material which is obvious in drug absorption promoting effect and low in toxicity. The chitosan modified by the fluorine-containing compound hasthe advantages of mature synthesis process, simplicity and easiness in operation, high synthesis efficiency and short period, a high-yield drug carrier can be obtained without complicated purification steps, and a good commercialized foundation is provided for the fluorinated modified chitosan derivative by a simple synthesis method.

Description

technical field [0001] The invention relates to the technical fields of polymer chemistry and medical biomaterials, in particular to a chitosan polymer drug carrier based on fluoride modification and its preparation method and application. Background technique [0002] In recent years, hydrophilic cationic polymer materials such as polyethyleneimine (PEI), polylysine and other cationic properties can combine with nucleic acid, polypeptide and protein molecules to form nanocomposites, which not only promote the entry of these macromolecular compounds into cells, Moreover, it can protect the drug from being degraded by hydrolytic enzymes in the microenvironment, and its internal tertiary ammonia structure promotes the escape of the drug in the endosome of the cell through the action of the proton sponge. At the same time, because the cationic polymer material can increase the permeability of the epithelium by weakening the tight junction of the epithelial cells, and promote th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/36A61K31/704A61P35/00
CPCC08B37/003A61K47/36A61K31/704A61P35/00Y02A50/30A61K31/196A61K9/0014A61K9/0048A61K8/492A61Q19/00A61K2800/10A61K8/736A61Q7/00A61K8/43A61K8/606A61K8/44A61Q19/02A61K2800/56A61K2800/54C08L5/08A61K47/61A61K47/542A61K47/54
Inventor 刘庄赵琪金秋桐朱文俊
Owner SUZHOU UNIV
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