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Oxidation-responsive PEGlated lipid material, and preparation method and application thereof

A technology of lipid materials and click chemical reactions, which can be used in pharmaceutical formulations, medical preparations of non-active ingredients, emulsion delivery, etc., and can solve problems that have not been reported.

Active Publication Date: 2017-10-20
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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  • Oxidation-responsive PEGlated lipid material, and preparation method and application thereof
  • Oxidation-responsive PEGlated lipid material, and preparation method and application thereof
  • Oxidation-responsive PEGlated lipid material, and preparation method and application thereof

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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 invention provides a PEGlated lipid material, and a preparation method and an application thereof. The material has a structure represented by formula (I). The material has oxidation responsiveness, and can be used as a drug carrier. An experiment result shows that the material is amphiphilic, undergoes phenylboronate oxidation removal in the presence of H2O2, and further undergoes a quinine-methide rearrangement reaction to realize the dissociation of a hydrophilic chain segment and a hydrophobic chain segment of the PEGlated lipid material; and the material entraps celecoxib and is self-assembled to form nano-micelles, the particle size of nano-particles is about 90 nm, and the hydrodynamic radius of the nano-micelles is 41.5-44.5 nm; and the entrapping rate is 54%, and the drug loading capacity 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 Applications(China)
IPC IPC(8): C08G65/333A61K9/107A61K47/22
CPCA61K9/1075A61K47/22C08G65/33396
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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