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

A cationic polymer and compound technology, which is applied in the field of cationic polymer as a drug carrier and its preparation, can solve the problems of mucous membrane, epithelial injury, toxic side effects of the body, poor biocompatibility, 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

However, this delivery system has poor biocompatibility, has certain toxic and side effects on the body, and can easily cause mucosal and epithelial damage at high concentrations, and its clinical application faces bottlenecks.

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1-1

[0294] Example 1-1: Preparation of chitosan with different degrees of modification of 3-fluorobenzoic acid (degree of deacetylation≧95%, viscosity 100-200 mpa.s), wherein the feeding mole of 3-fluorobenzoic acid and N-glucosamine unit The ratios are 1:1.1, 1:2.2, 1:4.4, 1:8.8.

[0295] Synthetic method: (1) Preparation of chitosan acetic acid aqueous solution: Weigh 200 mg of fully dried chitosan and add it to 10 ml of 1% acetic acid aqueous solution. Of course, hydrochloric acid aqueous solution can also be used. Stir for 30 minutes to fully dissolve, then slowly add 1.6 ml of 0.5 M 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 a...

Embodiment 1-2

[0297] Example 1-2: Preparation of chitosan with different modification degrees 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.

[0298] 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 chi...

Embodiment 1-3

[0300] Example 1-3: 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.

[0301] 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) Prep...

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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 1000 to 5000000; the deacetylation degree is not less than 55%, and the viscosity range is 25-1000 centipoises; the fluorine-containing compound is a fluorine-containing aliphatic chain shown in the following chemical formula (I) or an aromatic ring functional group shown in the formula (II), and R1 is halogen (fluorine, chlorine,bromine and iodine), halogen substituted alkane, cycloalkane, aldehyde group, carboxyl, double bond, acetylene bond, hydroxyl, sulfonyl chloride, sulfonic acid bond or sulfydryl and other active groups capable of reacting with primary amino. The fluorine-containing compound modified cationic polymer has the advantages that the fluorine-containing compound modified cationic polymer can be universally combined with various medicines, the medicine absorption is promoted, the bioavailability of the medicines is improved, the toxicity is reduced, the effect is good, the application is very wide, the huge commercial value is realized, and the fluorine-containing compound modified cationic polymer is simple and easy to produce and has a commercial foundation.

Description

technical field [0001] The invention relates to the technical fields of macromolecule chemistry and medical biomaterials, in particular to cationic polymers modified based on fluoride as drug carriers and their preparation methods and applications. 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 p...

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 刘庄陈倩金秋桐赵琪肖志晟韦婷沈菁菁
Owner SUZHOU UNIV
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