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A kind of oxidation-responsive PEGylated lipid material, its preparation method and application

A lipid material, click chemical reaction technology, which can be used in pharmaceutical formulations, medical preparations of inactive ingredients, emulsion delivery, etc., and can solve problems such as unreported

Active Publication Date: 2019-09-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, PEGylated lipid materials with pH response, reduction response and enzyme response have been reported, however, PEGylated lipid materials with oxidation response have not been reported.

Method used

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  • A kind of oxidation-responsive PEGylated lipid material, its preparation method and application
  • A kind of oxidation-responsive PEGylated lipid material, its preparation method and application
  • A kind of oxidation-responsive PEGylated lipid material, its preparation method and application

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preparation example Construction

[0043] The present invention provides a method for preparing an oxidation-responsive PEGylated lipid material described in the above technical solution, comprising the following steps:

[0044] In the presence of a catalyst and a solvent, the polyethylene glycol monomethyl ether derivative having the structure of formula (II) and the azide diglyceride of fatty acid having the structure of formula (III) are click chemically reacted to obtain the structure of formula (I) Oxidation-responsive PEGylated lipid materials;

[0045]

[0046] In formula (II), 10≤m≤500;

[0047]

[0048] In formula (III), 0≤n≤20.

[0049] In the present invention, in order to distinguish it from the catalyst in the following technical scheme, the polyethylene glycol monomethyl ether derivative with the structure of formula (II) and the azidated fatty acid glyceride with the structure of formula (III) are clicked The catalyst used in the chemical reaction is named as the first catalyst. The firs...

Embodiment 1

[0081] Synthesis of Carboxylated Polyethylene Glycol Monomethyl Ether

[0082] Weigh 7.5 g of polyethylene glycol monomethyl ether (molecular weight 750), 5 g of succinic anhydride, 244.3 mg of 4-dimethylaminopyridine, and 80 ml of dichloromethane, and add them into the reaction flask. Stir at room temperature for 48h. Part of the solvent was evaporated by rotary evaporation, and settled 3 times with anhydrous ether to obtain mPEG 0.75k -COOH.

Embodiment 2

[0083] Embodiment 2: the synthesis of the polyethylene glycol monomethyl ether of terminal carboxylation

[0084] Weigh 20 g of polyethylene glycol monomethyl ether (molecular weight: 2000), 5 g of succinic anhydride, 244.3 mg of 4-dimethylaminopyridine, and 120 ml of dichloromethane, and add them into the reaction flask. Stir at room temperature for 48h. Part of the solvent was evaporated by rotary evaporation, and settled 3 times with anhydrous ether to obtain mPEG 2k -COOH.

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Abstract

The present invention provides a PEGylated lipid material, its preparation method and application. The material has the structure of formula (I). The material has oxidation responsiveness and can be used as a drug carrier. The experimental results show that the material is amphiphilic and can be 2 o 2 In the existing environment, the phenylboronic ester in the structure of formula (I) is oxidized and removed, and the quinone-methide rearrangement reaction occurs further, resulting in the dissociation of the hydrophilic and hydrophobic segments of the PEGylated lipid material; and the material contains Celecoxib self-assembles to form nanomicelles, the particle size of the nanoparticles is about 90nm, and the hydrodynamic radius of the nanomicelles is 43±1.5nm; the encapsulation efficiency is 54%, and the drug loading is 5.4%.

Description

technical field [0001] The invention relates to the technical field of new polymer materials, in particular to an oxidation-responsive PEGylated lipid material, its preparation method and its application. Background technique [0002] When liposome is used as a passive targeting agent for drug delivery, it is easily taken up by the reticuloendothelial system (RES) due to the recognition of opsonins in plasma, thereby reducing the probability of specific binding to cancerous tissue cells. In order to overcome this defect, researchers inserted liposome derivatives with hydrophilic segments into the bilayer of liposomes to increase the hydrophilicity and steric hindrance of the liposome surface to prolong the circulation in vivo. time, increasing the accumulation of liposomes in tumor tissues or organs. The most widely used hydrophilic segment is polyethylene glycol. [0003] Traditional PEG-1ipid derivatives such as polyethylene glycol-distearoylphosphatidylethanolamine (PEG...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/333A61K9/107A61K47/22
Inventor 肖春生张田慧庄秀丽陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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