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Amphiphilic pH-responsive 4/6 heteroarm star-shaped copolymer and preparation method thereof

A star-shaped copolymer and amphiphilic technology, which is applied in the field of amphiphilic pH-responsive 4/6 heteroarm star-shaped copolymer and its preparation, can solve problems such as the difficulty of determining the number of arms, and achieve easy regulation, simple operation, The effect of mild reaction conditions

Active Publication Date: 2013-10-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The arm-first-nucleus method requires the synthesis of monofunctional active linear macromolecules first, and the arm lengths of the synthesized star polymers are the same, but the number of arms is difficult to determine

Method used

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  • Amphiphilic pH-responsive 4/6 heteroarm star-shaped copolymer and preparation method thereof
  • Amphiphilic pH-responsive 4/6 heteroarm star-shaped copolymer and preparation method thereof
  • Amphiphilic pH-responsive 4/6 heteroarm star-shaped copolymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of amphiphilic pH-responsive 4-arm star copolymer

[0060] (1) Preparation of pentaerythritol diester of 2-bromoisobutyrate, a small molecule initiator: Weigh 6.08g (0.05mol) of pentaerythritol (Alfa-Aesar) in a 250mL three-neck flask, add 150mL of anhydrous THF, and blow argon for 10min to remove oxygen. After sealing the flask, 10.12 g (0.1 mol) of triethylamine (TEA, AR, Jiangsu Yonghua) was injected. 22.98 g (0.1 mol) of 2-bromoisobutyryl bromide (Alfa-Aesar) was injected dropwise into an ice-water bath at 0°C, stirred for 4 hours, and then stirred at room temperature for 30 hours at 25°C. Transfer the reaction solution into a separatory funnel, add 300mL of ether, and extract with 200mL of water, 200mL of 0.5M sodium bicarbonate solution and 200mL of water in sequence, the organic phase is dried with anhydrous magnesium sulfate and filtered, and the solution is rotary evaporated to obtain a white solid (The yield is 56%). After recrystalliz...

Embodiment 2

[0069] Example 2: Preparation of amphiphilic pH-responsive 4-arm star copolymer

[0070](1) Preparation of pentaerythritol diester of 2-bromoisobutyrate, a small molecule initiator: Weigh 6.08g (0.05mol) of pentaerythritol (Alfa-Aesar) in a 250mL three-neck flask, add 150mL of anhydrous THF, and blow argon for 10min to remove oxygen. After sealing the flask, 10.12 g (0.1 mol) of TEA (AR, Jiangsu Yonghua) was injected. 22.98 g (0.1 mol) of 2-bromoisobutyryl bromide (Alfa-Aesar) was injected dropwise into an ice-water bath at 0°C, stirred for 6 hours, and then stirred at room temperature for 16 hours at 25°C. Transfer the reaction solution into a separatory funnel, add 300mL of ether, and extract with 200mL of water, 200mL of 0.5M sodium bicarbonate solution and 200mL of water in sequence, the organic phase is dried with anhydrous magnesium sulfate and filtered, and the solution is rotary evaporated to obtain a white solid (The yield is 56%), after recrystallization twice from...

Embodiment 3

[0075] Example 3: Preparation of amphiphilic pH-responsive 4-arm star copolymer

[0076] (1) Preparation of pentaerythritol diester of 2-bromoisobutyrate, a small molecule initiator: Weigh 6.08g (0.05mol) of pentaerythritol (Alfa-Aesar) in a 250mL three-neck flask, add 150mL of anhydrous THF, and blow argon for 10min to remove oxygen. After sealing the flask, 10.12 g (0.1 mol) of TEA (AR, Jiangsu Yonghua) was injected. 22.98 g (0.1 mol) of 2-bromoisobutyryl bromide (Alfa-Aesar) was injected dropwise into an ice-water bath at 0°C, stirred for 5 h, and then stirred at room temperature for 24 h at 25°C. Transfer the reaction solution into a separatory funnel, add 300mL of ether, and extract with 200mL of water, 200mL of 0.5M sodium bicarbonate solution and 200mL of water in sequence, the organic phase is dried with anhydrous magnesium sulfate and filtered, and the solution is rotary evaporated to obtain a white solid (The yield is 56%), after recrystallization twice from diethy...

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Abstract

The invention belongs to the technical field of high molecular polymer materials for biomedicine, and discloses an amphiphilic pH-responsive 4 / 6 heteroarm star-shaped copolymer of which the number-average molecular weight is 30000-54000g / mol. The invention also discloses a preparation method of the amphiphilic pH-responsive 4 / 6 heteroarm star-shaped copolymer, which comprises the following steps: mixing epsilon-caprolactone, stannous octoate and low molecular initiator, reacting at 110-140 DEG C for 24-48 hours, performing reduced pressure distillation, precipitating, filtering, and drying to obtain polycaprolactone high molecular initiator; dissolving the polycaprolactone high molecular initiator, 2-diethylaminoethyl methacrylate, hexamethyltriethylenetetramine and copper bromide in toluene, stirring, then adding stannous octoate, and reacting at 60-90 DEG C for 5-12 hours; and adding methoxy polyoxyethylene methacrylate, continuously polymerizing for 5-12 hours, removing a catalyst, filtering, and performing posttreatment on the filtrate to obtain the amphiphilic pH-responsive 4 / 6 heteroarm star-shaped copolymer. The amphiphilic pH-responsive 4 / 6 heteroarm star-shaped copolymer is used for preparation of a micelle system for carrying water insoluble medicaments.

Description

technical field [0001] The invention belongs to the technical field of high-molecular polymer materials for biomedicine, and in particular relates to an amphiphilic pH-responsive 4 / 6 heteroarm star copolymer and a preparation method thereof. Background technique [0002] Cancer is one of the three major diseases in the 21st century, seriously endangering human health. According to the World Health Organization's global cancer report, more than 7 million people are killed every year around the world. With the aging of the world's population, the number of cancer deaths worldwide is expected to increase rapidly, and may exceed 13.1 million by 2030. Due to the heterogeneity of cancer cells, multidrug resistance, etc., the treatment of cancer drugs still faces great challenges. As one of the most important tools to fight cancer, chemotherapy plays a very important role in the treatment of cancer. Ideal chemotherapeutic drugs should only work on cancer cells at the diseased sit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/34C08F220/28C08G63/08A61K47/34
CPCC08F220/34C08F293/005C08F2438/01C08G63/08C08F220/286
Inventor 章莉娟林文静杨友强聂淑瑜
Owner SOUTH CHINA UNIV OF TECH
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