Synthetic method of non-linear structure polycaprolactone-block-polyethyleneglycol

A polyethylene glycol, polycaprolactone technology, applied in the chemical industry, can solve the limitation, difficult copolymer degradation and drug controlled release performance, no polycaprolactone-block-polyethylene glycol preparation method is provided, etc. problem, to achieve the effect of convenient operation and simple steps

Inactive Publication Date: 2008-12-24
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its weak point is: 1. this document does not provide the preparation method of the polycaprolactone-block-polyethylene glycol of non-linear topological structure (fan-linear and fan-linear-fan)
2. This document is only used for the synthesis of polycaprolactone-graft-polyethylene glycol with a linear structure, and the refunctionalization of the material is not possible, and it is difficult to adjust the degradation of the copolymer and the controlled drug release performance
3. When this document prepares α-chlorocaprolactone, it is necessary to use peroxyacid reagents, so that it is limited in laboratory and industrial production

Method used

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Embodiment 1

[0015] Synthetic method of polycaprolactone-block-polyethylene glycol with sector-linear structure

[0016] Polyethylene glycol with azide-terminated linear structure (PEO-N 3 ) with a linear structure of alkynylated polycaprolactone (Dm-PCL) in a one-step "click chemistry" reaction: Weighing polyethylene glycol PEO-N with azidated linear structure 3 (110.0mg, 0.219mmol) and linear structure alkynylated polycaprolactone Dm-PCL (118.1mg, 0.199mmol alkynyl) were added to a 25mL eggplant-shaped reaction flask, completely dissolved in 2mL DMF, and bromine was added under nitrogen Cuprous chloride (CuBr, 3.1 mg, 0.0219 mmol) was reacted with pentamethyldivinyltriamine (PMDETA, 5 μL, 0.0219 mmol) at 35° C. for 24 hours. After the reaction, the polymer solution was settled in a large amount of ether, and purified by solvent extraction with 10 mL of cold methanol (about 10 °C) to completely remove excess PEO-N 3 . The product was vacuum-dried at 40° C. to obtain 158.5 mg of fan-lin...

Embodiment 2

[0018] Synthetic method of polycaprolactone-block-polyethylene glycol with fan-linear-fan structure

[0019] Double-terminal azidated linear polyethylene glycol (N 3 -PEO-N 3 ) with a linear structure of alkynylated polycaprolactone (Dm-PCL) one-step "click chemistry" reaction: Weigh the two-terminal azidated linear structure of polyethylene glycol N 3 -PEO-N 3 (50.0mg, 0.0123mmol) and linear structure alkynylated polycaprolactone Dm-PCL (131.6mg, 0.0272mmol alkynyl) were added to a 25mL eggplant-shaped reaction flask, completely dissolved in 1.5mL DMF, and added under nitrogen Cuprous bromide (CuBr, 3.9 mg, 0.0272 mmol) was reacted with pentamethyldivinyltriamine (PMDETA, 6 μL, 0.0272 mmol) at 35° C. for 36 hours. After the reaction, the polymer solution was settled in a large amount of ether. Using a solvent extraction method, a mixed solution of benzene and n-hexane (10 mL, benzene:n-hexane=0.7:1, volume ratio) was used to completely remove excess Dm-PCL. The product w...

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Abstract

The invention discloses a method for synthesizing polycaprolactone-block-polyethylene glycol with a non-linear structure in the chemical technical field, which is finished through a one-step click chemical reaction, namely the method is finished by polycaprolactone with an acetylene terminated sector structure and polyethylene glycol with an azido-terminated linear structure through a click chemical reaction, and the reaction takes cuprous bromide and pentamethyldiethylenetriamine as a co-catalyst and is performed in a N, N-dimethylformamide solution. The method provides a simple and effective approach for the preparation of degradable amphiphilic biomedical polymers with non-linear structures, and provides a theoretical evidence for obtaining a novel polymer drug carrier with controllable degradation rate and drug release rate.

Description

technical field [0001] The invention relates to a method in the technical field of chemical engineering, in particular to a method for synthesizing non-linear polycaprolactone-block-polyethylene glycol. Background technique [0002] Biodegradable polymer polycaprolactone and its copolymers have been extensively studied in recent years in the fields of controlled drug release systems, tissue engineering, and bionanotechnology. However, the further clinical application of biodegradable polymers is hindered by strong hydrophobicity, poor cell adhesion, uncontrollable material degradation and drug release rate, and lack of biological activity to induce cell, tissue or organ regeneration. Therefore, designing biodegradable polymers with controllable degradation and drug release rates, bioactive functions, and intelligence will provide an effective way to solve this problem, which has important theoretical significance and broad application prospects. Click chemistry is an effici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91C08G65/48
Inventor 董常明华崇杨阳
Owner SHANGHAI JIAO TONG UNIV
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