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A kind of phosphorylcholine polyethylene glycol modified chitosan and preparation method thereof

A polyethylene glycol modification and phosphorylcholine technology, which is applied in the field of biomaterials and biomedical polymer materials, can solve the problems of poor hydrophilicity of nanospheres, achieve non-toxicity, simple method, and high yield Effect

Active Publication Date: 2019-05-28
南通药享科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the slow release is expected to avoid the excessive blood concentration of gentamicin sulfate in the body, thereby inhibiting the generation of toxic and side effects, but due to the poor hydrophilicity of nanospheres, it may cause adverse reactions such as blood coagulation, thus limiting its use. application

Method used

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  • A kind of phosphorylcholine polyethylene glycol modified chitosan and preparation method thereof
  • A kind of phosphorylcholine polyethylene glycol modified chitosan and preparation method thereof
  • A kind of phosphorylcholine polyethylene glycol modified chitosan and preparation method thereof

Examples

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preparation example Construction

[0052] 1. Preparation of phosphorylcholine-based polyethylene glycol

[0053] Dissolve 0.1 mol of monoamino-terminated polyethylene glycol (n=10) in N,N-dimethylformamide, add 0.12 mol of hexanaldophosphorylcholine compound, react at 50°C for 12 hours, and cool After cooling down to 8°C, add NaBH with a concentration of 0.02g / mL 4 Methanol solution (wherein NaBH 4 The amount of the substance is 0.24 mol), the temperature was raised to 20°C, the reaction was carried out for 12 hours, 6 times the volume of glacial ether was settled, suction filtered, washed with glacial ether, and dried under vacuum at room temperature to obtain polyethylene glycol with a phosphorylcholine group at the end.

[0054] 2. Preparation of acrylate-capped phosphorylcholine-based polyethylene glycol

[0055] Dissolve 0.01mol of phosphorylcholine-based polyethylene glycol (n=10) and 0.012mol of triethylamine in anhydrous dichloromethane, cool down to -5°C to 3°C, slowly add 0.012mol of acryloyl chlori...

Embodiment 1

[0066] Dissolve 1g of chitosan (95% degree of deacetylation, molecular weight: 200,000) in 10mL of 0.1mol / L acetic acid aqueous solution, deoxygenate with nitrogen, add 0.027g of potassium persulfate (0.01mol / L), react at 60°C for 30min, Cool down to 50°C, add 0.2g of acrylate-capped phosphorylcholine-based polyethylene glycol, react for 6h under nitrogen, adjust pH to 8-9 with 5% sodium hydroxide solution, filter, and filter the cake with 80% Wash with ethanol and acetone, and vacuum-dry at 35°C to constant weight to obtain phosphorylcholine-based polyethylene glycol-modified chitosan (number-average molecular weight: 132,000). Depend on figure 1 It can be seen that the phosphorylcholine-based polyethylene glycol-modified chitosan nanoparticles prepared in this example have regular shapes, no agglomeration, and smooth surfaces.

[0067] Weigh 0.1g, 0.25g, 0.4g, 0.6g of phosphorylcholine-based polyethylene glycol-modified chitosan and slowly add them to 5mL deionized water un...

Embodiment 2

[0069] Dissolve 1g of chitosan (90% degree of deacetylation, molecular weight: 250,000) in 10mL of 0.1mol / L acetic acid aqueous solution, deoxygenate with nitrogen, add 0.027g of ammonium persulfate (0.01mol / L), react at 60°C for 30min, Cool down to 50°C, add 0.4g of acrylate-capped phosphorylcholine-based polyethylene glycol, react for 6h under nitrogen, adjust pH to 8-9 with 5% sodium hydroxide solution, filter, and use 80% ethanol, Washed with acetone, dried in vacuum at 35°C to constant weight to obtain phosphorylcholine-based polyethylene glycol-modified chitosan (number-average molecular weight: 176,000).

[0070] Weigh 0.25g of phosphorylcholine-based polyethylene glycol-modified chitosan and slowly add it to 5mL deionized water under magnetic stirring to obtain phosphorylcholine-based polyethylene glycol-modified chitosan nanoparticles, denoted as C2, the concentration is 5g / dL.

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Abstract

The invention discloses phosphorylcholine polyethylene glycol modified chitosan and a preparation method thereof. The number-average molecular weight of the phosphorylcholine polyethylene glycol modified chitosan is 0.13 to 0.41 million, and the chemical structural formula of the phosphorylcholine polyethylene glycol modified chitosan is as shown in the description, wherein PC is as shown in the description, and n is equal to 4 to 50. The preparation method comprises the step of adopting chitosan and acrylate-terminated phosphorylcholine polyethylene glycol to carry out free radical polymerization so as to obtain the phosphorylcholine polyethylene glycol modified chitosan. The phosphorylcholine polyethylene glycol is introduced onto the chitosan, other reagents do not need to be introduced, a nanoparticle structure with a chitosan chain segment as a core and the phosphorylcholine polyethylene glycol on the surface can be self-assembled in water, meanwhile, the introduced phosphorylcholine polyethylene glycol chain segment has good water solubility, biocompatibility and flexibility, and phosphorylcholine radical is positioned at the tail end of the flexible polyethylene glycol, so that a simulated cell outer layer membrane structure is self-assembled more easily.

Description

technical field [0001] The invention relates to the technical field of biomaterials, in particular to the field of biomedical polymer materials, in particular to a phosphorylcholine-based polyethylene glycol-modified chitosan and a preparation method thereof. Background technique [0002] With the rapid development of biotechnology, biomedical materials have become a hot spot in the current scientific research field. However, in the clinical application of existing biomedical materials and devices, problems such as infection, blood coagulation, and postoperative tissue hyperplasia exist to varying degrees. These biocompatibility problems have become key factors restricting the clinical application of biomedical materials. Currently, surface modification of materials is a very effective way to improve their biocompatibility. [0003] As a degradable polymer biomaterial, chitosan (CS) is an ideal carrier for the preparation of nano-medicines. It has various biological activit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K47/36A61L27/20A61L27/58A61L27/50C12N15/87
CPCA61K47/36A61L27/20A61L27/50A61L27/58C08B37/003C12N15/87C08L5/08
Inventor 侯昭升徐魏魏刘路路原栎潼贾骐尹胜男
Owner 南通药享科技有限公司
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