Derivative of amphoteric chitosan, preparation method, and application in pharmacy

A technology of chitosan derivatives and amphiphilicity, which is applied in the field of amphiphilic chitosan derivatives and its preparation, can solve problems such as unclear degradation mechanisms, achieve long circulation, good biocompatibility, reduce devouring effect

Inactive Publication Date: 2007-10-10
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Ping Qineng et al. (Chinese patent, application number: 03112981.1, authorized announcement date August 16, 2006) invented N-long chain alkyl-O-sulfonic chitosan derivatives, which can form 100-400nm Nanoparticles, and some p...

Method used

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  • Derivative of amphoteric chitosan, preparation method, and application in pharmacy
  • Derivative of amphoteric chitosan, preparation method, and application in pharmacy

Examples

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Embodiment 1

[0029] Embodiment 1: Preparation of O-oleic acid-N-polymalic acid chitosan nanoparticles

[0030] One, the preparation of oleic acid chloride

[0031] Dissolve oleic acid (2.82 g) in 20 mL of dry dichloromethane under a nitrogen atmosphere, stir in an ice bath, slowly add dropwise a solution of 2 mL of oxalyl chloride dissolved in 10 mL of dry dichloromethane, continue stirring at room temperature for 5 hours, and The excess oxalyl chloride and solvent were removed under reduced pressure to obtain 3 g of oleic acid chloride.

[0032] 2. Preparation of O-oleic acid chitosan

[0033] Take the molecular weight as 2×10 5 Add chitosan (0.8 g) with a degree of deacetylation above 90% into the solvent and stir until completely dissolved. According to the molar ratio of oleic acid chloride and chitosan unit 3:1 feed intake, at room temperature and N 2 Reacted for 8h under protection, and then added 20g of crushed ice to terminate the reaction. This mixture was dialyzed for 1 day ...

Embodiment 2

[0040] Embodiment 2: Preparation of O-oleic acid-N-polymalic acid chitosan nanoparticles

[0041] One, the preparation of oleic acid chloride

[0042] Dissolve oleic acid (2.82g) in 20mL of dry dichloromethane under a nitrogen atmosphere, stir in an ice bath, slowly add dropwise a solution of 2mL oxalyl chloride dissolved in 10mL of dry dichloromethane, continue to stir at room temperature for 1 hour, and dry in the tower The excess oxalyl chloride and solvent were removed under reduced pressure to obtain 3 g of oleic acid chloride.

[0043] 2. Preparation of O-oleic acid chitosan

[0044] Take the molecular weight as 5×10 4 Add chitosan (0.8 g) with a degree of deacetylation above 90% into the solvent and stir until completely dissolved. According to the molar ratio of oleic acid chloride and chitosan unit 5:1 feed intake, at room temperature and N 2 Reacted for 8h under protection, and then added 20g of crushed ice to terminate the reaction. This mixture was dialyzed fo...

Embodiment 3

[0049] Embodiment 3: Preparation of O-oleic acid-N-polymalic acid chitosan nanoparticles

[0050] One, the preparation of oleic acid chloride

[0051] Dissolve oleic acid (2.82 g) in 20 mL of dry dichloromethane under a nitrogen atmosphere, stir in an ice bath, slowly add dropwise a solution of 2 mL of oxalyl chloride dissolved in 10 mL of dry dichloromethane, continue stirring at room temperature for 8 hours, and dry The excess oxalyl chloride and solvent were removed under reduced pressure to obtain 3 g of oleic acid chloride.

[0052] 2. Preparation of O-oleic acid chitosan

[0053] Take the molecular weight as 1×10 6 Add chitosan (0.8 g) with a degree of deacetylation above 90% into the solvent and stir until completely dissolved. According to the molar ratio of oleic acid chloride and chitosan unit 1:1 feed intake, at room temperature and N 2 Reacted for 8h under protection, and then added 20g of crushed ice to terminate the reaction. This mixture was dialyzed for 1 ...

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Abstract

This invention discloses a method for preparing amphiphilic chitosan derivative and its pharmaceutical application. The method comprises: connecting acylchlorinated long-chain fatty acid and chitosan by esterification, connecting end-activated poly (benzyl malate) and O-long-chain alkyl chitosan via amido bond, and performing catalytic hydrogenation to remove protective groups and obtain amphiphilic chitosan derivative. The amphiphilic chitosan derivative can form nanoparticles of 100-300 nm in aqueous solution, and has such advantages as high biodegradability, high biocompatibility and easy modification.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to an amphiphilic chitosan derivative, a preparation method thereof and an application in pharmacy. Background technique [0002] In recent years, nano drug delivery system has many advantages such as targeted drug delivery, increased drug bioavailability, increased solubility of poorly soluble drugs, improved drug stability, long circulation in the body, and reduced phagocytosis by reticuloendothelial cells. Advantages, and become a research hotspot of drug delivery system. The polymer materials used in nano drug delivery systems are generally block or graft copolymers with hydrophilic components and hydrophobic components, so as to form a micellar structure with an inner hydrophobic core and an outer hydrophilic shell. At present, the research on the hydrophobic components of biodegradable polymer micelles usually has the following types: polyhydroxyesters, ...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K47/36
Inventor 印春华赵子明
Owner FUDAN UNIV
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