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Self-assembly nano-particles of sulfhydrylation chitosan quaternary ammonium salt and preparation method and application thereof

A technology of chitosan quaternary ammonium salt and chitosan quaternary amine, which is applied in the field of nanoparticles, can solve problems such as poor solubility, achieve simple process, promote intestinal absorption, and prevent drug inactivation

Inactive Publication Date: 2011-01-12
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor solubility of thiolated chitosan under neutral conditions, its further application is limited.

Method used

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  • Self-assembly nano-particles of sulfhydrylation chitosan quaternary ammonium salt and preparation method and application thereof
  • Self-assembly nano-particles of sulfhydrylation chitosan quaternary ammonium salt and preparation method and application thereof
  • Self-assembly nano-particles of sulfhydrylation chitosan quaternary ammonium salt and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1 The preparation of chitosan quaternary ammonium salt-cysteine ​​copolymer

[0064] According to the literature report method (Eur J Pharm Biopharm 2004,57:77-83) synthetic TMC, chitosan weight-average molecular weight is 30kDa, and reaction time is respectively 45min, 120min, 180min and 240min, and the degree of quaternization of gained TMC is respectively 15%, 30%, 60%, and 80%. Cl - Purify with anion exchange resin, freeze-dry; weigh 500mg TMC and dissolve in 50mL water, 2g cysteine ​​dissolve in 20mL water, mix, add EDAC and NHS with a final concentration of 300mM respectively, adjust the pH to 5.0, and react at room temperature for 5h. The reaction product was dialyzed against pH 5.0 HCl solution (MWCO 3500Da) at 4°C for 5 days, and freeze-dried. The reaction conditions of the blank control were the same except that EDAC / NHS was not added.

Embodiment 2

[0065] Embodiment 2 The preparation of chitosan quaternary ammonium salt-cysteine ​​copolymer

[0066] Synthesize TMC according to literature report method (Eur J Pharm Biopharm 2004,57:77-83), chitosan molecular weight is weight average 100kDa, reaction time is respectively 45min, 120min, 180min and 240min, the quaternization degree of gained TMC is respectively 15%, 30%, 60%, and 80%. Cl - Purify TMC with anion-exchange resin, freeze-dry; weigh 500mg TMC, dissolve in 50mL water, and dissolve 2g cysteine ​​in 20mL water, mix, add EDAC and NHS with a final concentration of 300mM respectively, adjust the pH to 3.0, and react at room temperature for 5h , the reaction product was dialyzed against pH 5.0 HCl solution (MWCO3500Da) at 4°C for 5 days, and freeze-dried. The reaction conditions of the blank control were the same except that EDAC / NHS was not added.

Embodiment 3

[0067] Embodiment 3 The preparation of chitosan quaternary ammonium salt-cysteine ​​copolymer

[0068] According to the literature report method (Eur J Pharm Biopharm 2004,57:77-83) synthetic TMC, chitosan weight average molecular weight is 200kDa, and reaction time is respectively 45min, 120min, 180min and 240min, and the degree of quaternization of gained TMC is respectively 15%, 30%, 60%, and 80%. Purify TMC with Cl-type anion exchange resin, dialyze, and freeze-dry; weigh 500mg TMC and dissolve it in 50mL water, and dissolve 2g cysteine ​​in 20mL water, mix, add EDAC and NHS with a final concentration of 300mM respectively, and adjust the pH to 4.0 , reacted at room temperature for 5 h, and the reaction product was dialyzed against pH 5.0 HCl solution (MWCO 3500 Da) at 4°C for 5 days, and freeze-dried. The reaction conditions of the blank control were the same except that EDAC / NHS was not added.

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Abstract

The invention belongs to the technical field of nano-particles, and relates to self-assembly nano-particles of a sulfhydrylation chitosan quaternary ammonium salt and a preparation method and application thereof. The sulfhydrylation chitosan quaternary ammonium salt is prepared from chitosan through quaterisation and sulfhydrylation modifications in turn. The nano-particles are generated from the positively charged sulfhydrylation chitosan quaternary ammonium salt and a negatively charged protein polypeptide medicament or a nucleic acid medicament through polyelectrolyte action. Compared with the prior art, the invention has the advantages that: the preparation process of the nano-particles is simple and easy to control, organic solvent is not needed, and the stability of medicaments can be effectively improved. Compared with the conventional chitosan quaternary ammonium salt nano particles, the nano-particles have better effects of promoting absorption of the protein medicament and promoting cell transfection of the nucleic acid medicament.

Description

technical field [0001] The invention belongs to the technical field of nanoparticles, and in particular relates to a self-assembled nanoparticle of mercapto-chitosan quaternary ammonium salt, a preparation method and an application thereof. Background technique [0002] Nanoparticles refer to solid colloidal particles with a particle size between 10-1000nm. Because it can improve the solubility and stability of drugs, prolong the circulation time in the body, and has a good slow and controlled release effect, it has been widely used in protein and gene drug delivery systems. The prior art discloses many methods for preparing nanoparticles, including solvent evaporation method, surface polymerization method, emulsification method, self-assembly method and the like. Positively charged polymer molecules and negatively charged drugs self-assemble into nanoparticles through electrostatic interaction. The preparation process does not require the use of organic solvents, heating, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/14A61K47/48A61K47/36A61K45/00A61K48/00A61K47/61
Inventor 印春华殷黎晨赵鑫毛裕民顾少华唐翠
Owner FUDAN UNIV
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