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Acid-sensitive amphiphilic star-shaped block copolymer as well as preparation method and application thereof

A technology of block copolymer and amphiphilic block, which is applied in the field of acid-sensitive amphiphilic star-shaped block copolymer, can solve the problems of difficult to precisely control polymer structure and molecular weight distribution, low reaction efficiency and so on.

Inactive Publication Date: 2014-02-05
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Most of the existing star-shaped block copolymers use polyethylene glycol and polyester with good biocompatibility to prepare amphiphilic star-shaped block copolymers with good biocompatibility, but most of the existing preparation methods react The efficiency is not high, and it is difficult to precisely control the structure and molecular weight distribution of the polymer; and there is no report on the introduction of acid-sensitive groups into amphiphilic star-shaped block copolymers

Method used

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  • Acid-sensitive amphiphilic star-shaped block copolymer as well as preparation method and application thereof
  • Acid-sensitive amphiphilic star-shaped block copolymer as well as preparation method and application thereof
  • Acid-sensitive amphiphilic star-shaped block copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1: Preparation of Trimellitic Acid Propargyl (TAPE)

[0082] Put the branch tube bottle and the ground glass stopper equipped with a stirrer in an oven at 120°C to dry for at least 24 hours, take it out, put the ground glass stopper on the branch tube bottle stopper and connect it to the double-row tube, and cool it to room temperature with an oil pump. Repeat pumping and inflation three times, and finally fill with argon. Under the condition of argon, tetrahydrofuran (THF, 50 mL), propargyl alcohol (PA, 0.5000 g, 8.92 mmol) and 4-dimethylaminopyridine ( DMAP, 0.9078 g, 7.44 mmol), stirred until the solution was clear and transparent, quickly weighed trimesoyl chloride (BTT, 0.6577 g, 2.48 mmol) and added it to a dropping funnel filled with tetrahydrofuran (10 mL), and kept in an ice-water bath Slowly add it dropwise to the mixture, put the reaction bottle into an oil bath set at 25°C, and react under stirring for 12 hours.

[0083] After the reaction, the prod...

Embodiment 2

[0084] Example 2: Acid-sensitive polycaprolactone intermediate (PA-PCL) terminated by a monoalkyne group 27 - a -Cl) preparation

[0085] After the branch tube bottle and the ground glass stopper equipped with a stirring bar were processed according to the method of Example 1, they were filled with argon, and under the condition of argon flow, quickly weighed stannous octoate [Sn(Oct) 2 , 0.4050 g, 1 mmol] into the branch tube, pumped and inflated three times, and finally filled with argon, and added anhydrous toluene (20 mL) and ? - caprolactone ( ? -CL, 4.5656 g, 40 mmol) and propargyl alcohol (0.1121 g, 2 mmol). The reaction bottle was filled with argon and moved to a 90 °C oil bath, and the reaction was stirred for 4 hours.

[0086] After the reaction, the product was concentrated, precipitated twice in diethyl ether (150 mL), and filtered with suction to obtain a white solid, which was dried in a vacuum oven at room temperature for 36 hours to obtain polycaprolactone ...

Embodiment 3

[0089] Embodiment Three: Azido-terminated polyethylene glycol monomethyl ether (mPEG 45 - a -N 3 ) preparation

[0090] Weigh polyethylene glycol monomethyl ether (mPEG 45 -OH, 4.0800 g, 2 mmol) and pyridinium 4-methylbenzenesulfonate (0.0503 g, 0.2 mmol) were added to a 100 mL branch vial equipped with a magnetic stirrer, and toluene (30 mL) was added, and the water twice, then dissolve the azeotropic mixture in anhydrous dichloromethane (50 mL), and slowly add 2-chloroethyl vinyl ether (1.0 mL, 10 mmol) and anhydrous dichloromethane in an ice-water bath Add the mixed solution of methane (10 mL) to the branched vial. After the dropwise addition, stir the reaction in an ice-water bath for 0.5 hours.

[0091]After the reaction, add 5% sodium carbonate aqueous solution to terminate the reaction, dilute with dichloromethane (40 mL), then add saturated sodium chloride phosphate buffer solution (pH 10.0, 10 mL), oscillate and let stand. Separate the lower organic phase, extrac...

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Abstract

The invention discloses an acid-sensitive amphiphilic star-shaped block copolymer as well as a preparation method and application thereof. The preparation method comprises the steps of firstly, preparing a three-functional-group alkynyl compound with a benzene ring as a core by adopting condensation reaction; then, performing ring-opening polymerization on a cyclic ester monomer by taking a small molecule of which one end contains hydroxyl and the other end contains alkynyl as an initiating agent to obtain a polyester molecular chain, and modifying the polyester molecular chain into a polyester chain of which the tail end contains a chlorine functional group; then, modifying polyethylene glycol monomethyl ether into a molecular chain of which the tail end contains an aldehyde acetal group and an azide group; finally, preparing the acid-sensitive amphiphilic star-shaped block copolymer through two steps of 'CuAAC (Cu catalyzed azide-alkyne cycloaddition)' click reaction, wherein the polymer is controllable in structure and molecular weight and relatively narrow in molecular weight distribution and has good biocompatibility and biodegradability. The copolymer prepared by the invention can encapsulate a hydrophobic anticancer drug through self assembly, and under an acidic condition, due to the fracture of the aldehyde acetal group, a micelle structure is destroyed and an encapsulated drug is released, so that the copolymer can be used as a carrier for controlled release drugs.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and in particular relates to an acid-sensitive amphiphilic star-shaped block copolymer, its preparation method and its application as a drug carrier. Background technique [0002] Amphiphilic polymers are generally composed of hydrophilic and hydrophobic segments. Since they can self-assemble into nanoparticles of various shapes in aqueous solution, such as micelles, vesicles, rods, and layers, they are widely used in biomedicine, ultra- Molecular and nanotechnology and other fields have broad application prospects. As we all know, most anticancer drugs have strong hydrophobicity, and the core-shell structure micelles formed by the self-assembly of amphiphilic polymers have a hydrophobic inner core and can be used to pack hydrophobic anticancer drugs, while hydrophilic The outer shell can stabilize the micelles and significantly improve the circulation time of the drug-loaded micelles...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91C08G65/48A61K47/34
Inventor 倪沛红胡健何金林张明祖
Owner SUZHOU UNIV
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