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Preparation method of novel amphiphilic polymer of deoxycholate-modified chitosan oligosaccharide

A technology of amphiphilic polymer and deoxycholic acid, which is applied in the field of amphiphilic polymer preparation to achieve the effects of high stability of reactants, improved solubility and uniform particle size distribution

Inactive Publication Date: 2019-10-22
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the absolute oral bioavailability of OA is only 0.7%  (<1 μg / mL)
This limits the application of OA in the medical field

Method used

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  • Preparation method of novel amphiphilic polymer of deoxycholate-modified chitosan oligosaccharide
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specific Embodiment approach 1

[0034] Specific embodiment one: this embodiment provides a kind of preparation method of the amphiphilic polymer of novel deoxycholic acid modified chitosan oligosaccharide, and specific implementation steps are as follows:

[0035] 1. Add chitosan oligosaccharide and deoxycholic acid to the organic solvent of dimethyl sulfoxide solution respectively, and control the concentration of the solutions in the range of 10-15 mg / mL and 30-35 mg / mL respectively, seal and ultrasonically disperse for 5 minutes , placed in a magnetic stirrer to stir to make it completely dissolved, forming a uniform dispersion of chitosan and deoxycholic acid.

[0036] 2. Add 1-3g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.7-1.5 g N-hydroxysuccinimide to the deoxycholic acid dispersion, The oligosaccharide solution was added dropwise to the stirring deoxycholic acid solution, and stirred for 24 hours. After the reaction, the solution was dialyzed in distilled water (1000Da dialysis...

specific Embodiment approach 2

[0040] Specific embodiment two: this embodiment provides a kind of preparation method of the amphiphilic polymer of novel deoxycholic acid modified chitosan oligosaccharide, and specific implementation steps are as follows:

[0041] 1. Add chitosan oligosaccharide and deoxycholic acid to the organic solvent of dimethyl sulfoxide solution respectively, and control the concentration of the solutions in the range of 10-15 mg / mL and 30-35 mg / mL respectively, seal and ultrasonically disperse for 5 minutes , placed in a magnetic stirrer to stir to make it completely dissolved, forming a uniform dispersion of chitosan and deoxycholic acid.

[0042] 2. Add 1-3g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.7-1.5 g N-hydroxysuccinimide to the deoxycholic acid dispersion, The oligosaccharide solution was added dropwise to the stirring deoxycholic acid solution, and stirred for 24 hours. After the reaction, the solution was dialyzed in distilled water (1000Da dialysis...

specific Embodiment approach 3

[0045] Specific embodiment three: this embodiment provides a kind of preparation method of the amphiphilic polymer of novel deoxycholic acid modified chitosan oligosaccharide, and specific implementation steps are as follows:

[0046] 1. Add chitosan oligosaccharide and deoxycholic acid to the organic solvent of dimethyl sulfoxide solution respectively, and control the concentration of the solutions in the range of 10-15 mg / mL and 30-35 mg / mL respectively, seal and ultrasonically disperse for 5 minutes , placed in a magnetic stirrer to stir to make it completely dissolved, forming a uniform dispersion of chitosan and deoxycholic acid.

[0047] 2. Add 1-3g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.7-1.5 g N-hydroxysuccinimide to the deoxycholic acid dispersion, The oligosaccharide solution was added dropwise to the stirring deoxycholic acid solution, and stirred for 24 hours. After the reaction, the solution was dialyzed in distilled water (1000Da dialys...

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Abstract

The invention discloses a preparation method of a novel amphiphilic polymer of deoxycholate-modified chitosan oligosaccharide. The preparation method is applied to the encapsulation of oleanolic acid,aims at improving the bioavailability and stability of the oleanolic acid, and comprises the following steps that 1, firstly, chitosan oligosaccharide and a deoxycholate solution are formed in an organic solvent; 2, the deoxycholate is grafted to the chitosan oligosaccharide to obtain the amphiphilic polymer of the deoxycholate-modified chitosan oligosaccharide; 3, the amphiphilic polymer is added into an organic solvent to form a deoxycholate-modified chitosan oligosaccharide dispersion solution; 4, an oleanolic acid solution is dropped into the deoxycholate-modified chitosan oligosaccharidesolution to form deoxycholate-chitosan oligosaccharide encapsulated oleanolic acid nanoparticles through self-assembly. The maximum encapsulation rate and drug loading rate of the obtained nanoparticles are 80.50% and 53.61% respectively, the particle diameter is 250 + / - 25 nanometers, the bioavailability of the oleanolic acid is significantly improved, the application of the physiological functions of the oleanolic acid in the medical field is enhanced, and a novel material is provided for an oral delivery system of hydrophobic drugs.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and in particular relates to a preparation method of a novel amphiphilic polymer of chitosan oligosaccharide modified by deoxycholic acid. Background technique [0002] Amphiphilic polymers (APs) refer to macromolecules that contain hydrophilic and hydrophobic segments in their main chain or side chains. Due to its unique amphiphilic structure, AP can self-assemble into various ordered supramolecular structures under certain conditions, including vesicles, micelles, nanoparticles, nanospheres, multi-chambered microcapsules, etc. Amphiphilic polymers can improve drug solubility, control drug release, and reduce nonspecific uptake by the reticuloendothelial system (RES). Due to its low critical micelle concentration, the amphiphilic copolymers can self-assemble into nanoscale polymers with a core-shell structure, while poorly soluble drugs can be efficiently incorporated into the hydroph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/51A61K47/36A61K47/28A61K31/56
CPCA61K9/5161A61K9/5123A61K31/56
Inventor 王振宇刘双
Owner HARBIN INST OF TECH
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