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A kind of degradable high pH sensitive polymer and its preparation method and application

A polymer and sensitive technology, applied in the field of drug carriers, can solve the problems of difficult adjustment of biodegradation performance at mutation points, wide mutation range, and low drug loading capacity, and achieve good blood compatibility, low surface energy, and good encapsulation Effect

Active Publication Date: 2021-10-19
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

[0007] Patent CN10931989A discloses a method for preparing light / pH-sensitive amphiphilic azobenzene polymer micelles. The prepared micelles are single-armed micelles, which have low drug loading and poor sealing of micelles, resulting in Problems such as low drug loading efficiency
[0008] The inventors found that the drug-loaded micelles reported above all have problems such as insufficient sensitivity to the pH of the medium, too wide mutation interval, difficult adjustment of the mutation point, and insufficient biodegradability.

Method used

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  • A kind of degradable high pH sensitive polymer and its preparation method and application
  • A kind of degradable high pH sensitive polymer and its preparation method and application
  • A kind of degradable high pH sensitive polymer and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0058] Add 0.5g benzoyl peroxide (Bz) to 11mL 6-caprolactone (I) 2 o 2 ), and 20mL of carbon tetrachloride solution of bromine (solution concentration is 0.8g / mL) was added dropwise, and reacted at room temperature for 1h. Dry over magnesium sulfate and filter to obtain the carbon tetrachloride solution of II; add 15 g of anhydrous sodium carbonate to the filtrate, heat to 70 ° C for 1 hour, and filter to obtain the carbon tetrachloride solution of III; Slowly add it dropwise to 20 mL of triethylaminomagnesium bromide in tetrahydrofuran (concentration: 1 g / mL) containing 0.4 g CuCl, and react at -20°C for 2 h. After the reaction was completed, the temperature of the reaction solution was raised to -5°C, and an equal volume of saturated ammonium chloride solution was slowly added dropwise to the reaction solution and continued to stir for 20 min, filtered by suction, separated, and the organic phase was washed 3 times with a saturated ammonium chloride solution. It was dried ...

Embodiment 2

[0061] Preparation of prepolymer A: four-arm polytetrahydrofuran polyol (7.5g, M n =1500g / mol), 17.12g of 3-(triethylamino)-6-caprolactone and 25mg of stannous octoate were dissolved in 20mL of N,N-dimethylformamide, and argon gas was introduced for 5 minutes to remove oxygen. The temperature of the oil bath was raised to 70°C, the reaction time was 48h, and then lowered to room temperature, settled three times with 120mL of methanol, filtered with suction, and vacuum-dried at 40°C to constant weight to obtain prepolymer A.

[0062] Preparation of the polymer shown in formula I: 9.80g of prepolymer A, 2.02g of carboxymethoxyphosphorylcholine and 0.98g of dimethylaminopyridine were dissolved in 20mL of dichloromethane and 1.65g of N,N'-bicyclic Hexyl carboximide was protected by dry argon, and the reaction was carried out under magnetic stirring at room temperature for 24 hours. Suction filtration, the filtrate was distilled at normal pressure to remove most of the dichloromet...

Embodiment 3

[0065] Preparation of prepolymer A: four-arm polytetrahydrofuran polyol (7.5g, M n =1500g / mol), 21.40g of 3-(triethylamino)-6-caprolactone and 25mg of stannous octoate were dissolved in 25mL of N,N-dimethylformamide, and argon gas was introduced for 5 minutes to remove oxygen. The temperature of the oil bath was raised to 75°C, the reaction time was 40h, and then lowered to room temperature, settled three times with 150mL of methanol, filtered with suction, and vacuum-dried at 40°C to constant weight to obtain prepolymer A.

[0066] Preparation of the polymer shown in formula Ⅰ: 11.56g of prepolymer A, 2.02g of carboxymethoxyphosphorylcholine and 0.98g of dimethylaminopyridine were dissolved in 20mL of dichloromethane and 1.65g of N,N'-dicyclohexyl Carboimide was protected by dry argon, and the reaction was carried out under magnetic stirring at room temperature for 24 hours. Suction filtration, the filtrate was distilled at normal pressure to remove most of the dichlorometha...

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Abstract

The present invention relates to a degradable high pH-sensitive polymer and its preparation method and application. The degradable high pH-sensitive polymer has a structure shown in formula I, wherein PC is R and m=20-40, n =4~6. The prepared drug-loaded micelles have high encapsulation efficiency, and have obvious expansion in weak acidic medium, and the expansion multiple has obvious mutation with the change of medium pH value. The prepared medicine has a sustained-release effective time of 1-3 days in weakly acidic medium.

Description

technical field [0001] The invention belongs to the technical field of drug carriers, and in particular relates to a degradable high pH-sensitive polymer and a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Amphiphilic block copolymers self-assemble to form micelles, which are applied to the controlled release of various anti-tumor drugs and become one of the most promising drug carrier materials. Polymer micelles are a class of nanoparticles formed by self-assembly of amphiphilic copolymers in aqueous solution. Lipophilic drug molecules can be physically wrapped into the hydrophobic core of the micelles, while the hydrophilic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/91C08G63/664A61K47/34
CPCA61K47/34C08G63/664C08G63/912
Inventor 侯昭升孙雨辰高雅张礼
Owner 无锡享源信息科技有限公司
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