O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide, and preparation method and application thereof

A technology for carboxymethyl chitosan oligosaccharide and chitosan oligosaccharide, which is applied in the fields of O-carboxymethyl-N, N-double-chain long alkylated chitosan oligosaccharide and its preparation and application, and can solve the problem of large volume of nanovesicles , chitosan has large molecular weight and small number, etc., to achieve the effect of controllable permeability, easy degradation and large drug loading.

Active Publication Date: 2017-09-15
无锡享源信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Traditional self-assembled nanovesicles use chitosan as raw material to prepare chitosan derivatives, but chitosan has a large molecular weight, and the prepared nanovesicles are large in volume, small in number, and low in yield

Method used

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  • O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide, and preparation method and application thereof
  • O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide, and preparation method and application thereof
  • O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide, and preparation method and application thereof

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preparation example Construction

[0034] O-carboxymethyl-N, N-double-chain long alkylated chitosan can be prepared through the preparation route of the present invention. First, it not only has antibacterial properties and moisture retention, but also maintains the original good composition of chitosan. membrane properties, biocompatibility and biodegradability. Secondly, the chitosan oligosaccharide not only has a carboxymethyl group, but also has a long alkyl side chain, which makes it amphiphilic, thus providing a basis for the preparation of vesicles with excellent performance.

[0035] The application provides a method for protecting the amino group of a preferred chitosan oligosaccharide, the steps of which are: preparing the chitosan oligosaccharide into an aqueous solution of chitosan oligosaccharide, dissolving the small molecule aldehyde compound in an organic solvent one to prepare an aldehyde solution, and dissolving The aldehyde solution is added to the chitosan oligosaccharide mixed solution, and...

Embodiment 1

[0067] (1) Synthesis of N-benzylidene chitooligosaccharides

[0068] Dissolve 5g of chitosan oligosaccharide in 100mL of deionized water, stir at room temperature to fully dissolve, then add 10mL of absolute ethanol, weigh 6.58g of benzaldehyde, dissolve it in 10mL of absolute ethanol, add to the above solution, stir, and react at 30°C for 4h. 4 times the volume of ethanol was settled, washed twice with ethanol, filtered with suction, and dried in vacuum to obtain N-benzylidene chitosan oligosaccharide.

[0069] (2) Synthesis of O-carboxymethyl-N-benzylidene chitooligosaccharides

[0070] Weigh 4g of the dried product in (1), swell in 20mL of isopropanol at room temperature for 1h, then place in an ice-salt bath to cool for 2h, slowly add 30mL of 50% NaOH solution dropwise, stir evenly, and continue in the ice-salt bath After swelling for 2 hours, slowly add 5 mL of isopropanol solution containing 3.23 g of chloroacetic acid dropwise. Stir in a water bath at 50°C for more th...

Embodiment 2

[0078] (1) Synthesis of N-benzylidene chitooligosaccharides

[0079] Dissolve 5g of chitosan oligosaccharide in 100mL of deionized water, stir at room temperature to fully dissolve, then add 10mL of absolute ethanol, weigh 6.58g of benzaldehyde, dissolve it in 10mL of absolute ethanol, add to the above solution, stir, and react at 30°C for 4h. 4 times the volume of ethanol was settled, washed twice with ethanol, filtered with suction, and dried in vacuum to obtain N-benzylidene chitosan oligosaccharide.

[0080] (2) Synthesis of O-carboxymethyl-N-benzylidene chitooligosaccharides

[0081] Weigh 4g of the dried product in (1), swell in 20mL of isopropanol at room temperature for 1h, then place it in an ice-salt bath to cool for 1h, slowly add 30mL of 50% NaOH solution dropwise, stir evenly, and continue in the ice-salt bath After swelling for 2 hours, slowly add 5 mL of isopropanol solution containing 3.23 g of chloroacetic acid dropwise. Stir in a water bath at 50°C for more...

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Abstract

The invention discloses an O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide, and a preparation method and an application thereof. The chemical structure of the O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide is shown in the description. The preparation method comprises the following steps: protecting the amino group of chitooligosaccharide by adopting a micro-molecular aldehyde compound, carrying out a carboxymethylation reaction on the C6-position hydroxyl group of the amino group protected chitooligosaccharide by adopting chloroacetic acid, removing the protection group for protecting the amino group to obtain O-carboxymethyl chitooligosaccharide, and carrying out an alkylation reaction on two H in the amino group of the O-carboxymethyl chitooligosaccharide through adopting long-chain fatty aldehyde to obtain the O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide. The method makes the C6-position hydroxy group in the chitooligosaccharide be carboxymethylated and have hydrophobous long alkyl side chains, so the chitooligosaccharide is amphiphilic; and the prepared O-carboxymethyl-N,N-double chain long alkylated chitooligosaccharide has antibiosis and moisture retention property, and keeps the original good film forming ability, biocompatibility and biodegradability of the chitooligosaccharide.

Description

technical field [0001] The invention relates to an O-carboxymethyl-N, N-double-chain long alkylated chitosan oligosaccharide, a preparation method and application thereof. Background technique [0002] Oligochitosan is a natural cationic polysaccharide that is safe, non-toxic, biodegradable, and has good biocompatibility. It is chitosan with a low degree of polymerization. It has the properties of chitosan and has better Biodegradability, good water solubility, etc., have broad application prospects in biomedical materials. [0003] Nano-controlled release systems include nanoparticles and nanocapsules. They are solid colloidal particles with a diameter between 10 and 500 nm, and the active components (drugs, bioactive materials, etc.) are located inside the particles through dissolution and encapsulation, or on the surface of the particles through adsorption and attachment. Nanoscale polymer particles are used as carriers for drug delivery and controlled release, which is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C07H5/06C07H1/00A61K9/127A61K47/36
CPCA61K9/0002A61K9/1273A61K47/36C07H1/00C07H5/06C08B37/003Y02P20/55
Inventor 侯昭升尹胜男
Owner 无锡享源信息科技有限公司
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