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Mixed micelle with hypoxia and pH double responsiveness and preparation method of mixed micelle

A mixed micelle, responsive technology, applied in the fields of polymer materials and biomedical engineering, can solve the problem of insufficient physiological system, and achieve the effect of broad application prospects.

Inactive Publication Date: 2018-10-12
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the single stimulus of hypoxia as a characteristic index is not sufficient for complex physiological systems.

Method used

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  • Mixed micelle with hypoxia and pH double responsiveness and preparation method of mixed micelle
  • Mixed micelle with hypoxia and pH double responsiveness and preparation method of mixed micelle
  • Mixed micelle with hypoxia and pH double responsiveness and preparation method of mixed micelle

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Weigh 1.12g p-hydroxyazobenzene, 0.65g N,N'-dicyclohexylcarbodiimide, 0.13g 4-dimethylaminopyridine and dissolve in dichloromethane and dimethylformamide 1:1 In the mixed solvent, weigh 2.004g of carboxylated monomethoxypolyethylene glycol and add it dropwise in the solution, the reaction is carried out under the protection of nitrogen, the reaction temperature is room temperature, and the reaction time is 24 hours. By-products were removed by vacuum filtration, and the collected product was precipitated in ice-cold diethyl ether. The product was transferred to a reaction flask, and cyclohexyl lactone and a catalyst, stannous isooctanoate, were added. Under an ice-water bath, vacuum was used to remove oxygen and nitrogen gas was introduced. The ice-water bath was removed, the reaction temperature was adjusted to 150° C., and the reaction time was 24 hours. After the product was cooled to room temperature, diethyl ether was used as a precipitant to precipitate the p...

Embodiment 2

[0026] (1) Weigh 0.93g p-hydroxyazobenzene, 0.54g N,N'-dicyclohexylcarbodiimide, 0.09g 4-dimethylaminopyridine and dissolve in dichloromethane and dimethylformamide 1:2 In the mixed solvent, weigh 1.84g carboxylated monomethoxypolyethylene glycol and add it dropwise to the solution. The reaction is carried out under the protection of nitrogen, the reaction temperature is room temperature, and the reaction time is 16 hours. Remove by filtration, collect the product and precipitate in frozen diethyl ether, transfer the product to a reaction flask, add 4.8g cyclocaprolactone, 0.47g catalyst stannous isooctanoate, under ice-water bath, vacuum to remove oxygen and pass nitrogen. The ice-water bath was removed, the reaction temperature was adjusted to 100°C, and the reaction time was 24 hours. After the product was cooled to room temperature, it was precipitated in the precipitating agent n-hexane to obtain the polymer PEG-Azo-PCL and dried in vacuum.

[0027](2) Weigh 5.6g of hydro...

Embodiment 3

[0030] (1) Weigh 1.58g of p-hydroxyazobenzene, 0.72g of N,N'-dicyclohexylcarbodiimide, and 0.21g of 4-dimethylaminopyridine and dissolve them in dichloromethane and dimethylformamide at a ratio of 1:2 2.14g carboxylated monomethoxypolyethylene glycol was added dropwise in the solution, the reaction was carried out under the protection of nitrogen, the reaction temperature was room temperature, and the reaction time was 20 hours, and the by-product was vacuum filtered Remove, collect the product and precipitate it in frozen ether, transfer the product to a reaction flask, add 6.4g cyclocaprolactone, 0.46g catalyst stannous isooctanoate, under ice-water bath, vacuum to remove oxygen and pass nitrogen. The ice-water bath was removed, the reaction temperature was adjusted to 150°C, and the reaction time was 28 hours. After the product was cooled to room temperature, it was precipitated in the precipitating agent cyclohexane to obtain the polymer PEG-Azo-PCL and dried in vacuum.

...

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Abstract

The invention belongs to the fields of biological materials and nano materials, and relates to a mixed micelle with hypoxia and pH double responsiveness and a preparation method of the mixed micelle.The method comprises the following specific steps: a product of an esterification reaction of carboxylated monomethoxypolyethylene glycol and p-hydroxyazobenzene is used as a macroinitiator to initiate atom transfer radical polymerization of a cyclocaprolactone monomer; ring-opening polymerization cyclohexanolide is used as a macroinitiator to initiate atom transfer radical polymerization of a N,N-diethylaminoethyl methacrylate monomer; and two block copolymers are used to prepare the mixed micelle by a solvent evaporation method according to a certain charge ratio. The mixed micelle preparedby the method provided by the invention has the hypoxia and pH dual responsiveness, and broad application prospects in biomedical applications, drug carriers, targeted therapies and the like; and thepreparation method provided by the invention is simple and easy to implement, the raw materials can be industrially produced, and the method has very good promotion and application value.

Description

technical field [0001] The invention belongs to the fields of polymer materials and biomedical engineering, and in particular relates to a mixed micelle with hypoxia and pH dual responsiveness and a preparation method thereof. Background technique [0002] p-Hydroxyazobenzene (4,4'-Azobenzenedihydroxy) has a highly symmetrical chemical structure. The hydroxyl groups at both ends serve as two functional groups, which can be connected to macromolecules with required properties, and the nitrogen-nitrogen double bond at the center of symmetry can be used at low Fragmentation due to loss of electrons in an oxygen-containing environment. The new amphiphilic block copolymer materials prepared by using azo bonds as oxygen-deficiency responsive functional groups have attracted great attention because of their unique preparation methods and excellent properties. Kulkarni P et al. (Kulkarni P, Haldar M K, You S, et al. Biomacromolecules, 2016, 17(8): 2507.) synthesized a poly(ethylene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/03C08G65/333C08G63/08C08G63/664C08F293/00C08F220/34
CPCC08F220/34C08F293/005C08F2438/01C08G63/08C08G63/664C08G65/33396C08J3/03C08J2353/00C08J2367/04C08J2453/00C08J2467/04
Inventor 袁伟忠杨博文谢晓云
Owner TONGJI UNIV
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