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Preparation method and application of crown ether modified segmented copolymer micelle

A technology of block copolymer and crown ether, applied in the field of preparation of block copolymer micelles, can solve the problems of side effects, premature interpretation, non-specific absorption of curative effect, etc.

Active Publication Date: 2020-08-28
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Cancer has long been a threat to human life, and traditional treatments such as chemotherapy can have serious side effects
In addition, the efficacy of traditional chemotherapy drugs is limited by non-specific uptake and premature interpretation

Method used

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  • Preparation method and application of crown ether modified segmented copolymer micelle
  • Preparation method and application of crown ether modified segmented copolymer micelle
  • Preparation method and application of crown ether modified segmented copolymer micelle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The preparation method of the crown ether modified micelle of the present embodiment comprises the following steps:

[0055] S1, 1.0 grams of carboxy-polyethylene glycol 5000-hydroxyl (COOH-PEG 5000 -OH) was dissolved in 10ml toluene to obtain a concentration of the first reaction solution of 10mg / ml;

[0056] S2. The temperature of the first reaction solution was raised to 100° C., and 80 microliters (about 0.1 g) of stannous octoate was added, followed by 1.2 grams of caprolactone, and reacted for 24 hours under slow stirring conditions, and the reaction product was poured into glacial ether, washed with ether three times after centrifugation, and then freeze-dried to obtain about 1.9 g of COOH-PEG 5000 -PCL (carboxy-polyethylene glycol 5000-polycaprolactone), the yield is 86.36%; the NMR characterization diagram of carboxyl-polyethylene glycol 5000-polycaprolactone prepared in this example is shown in figure 1 .

[0057] The stannous isooctanoate is COOH-PEG 5000...

Embodiment 2

[0062] Embodiment 2 (comparative example)

[0063] The preparation method of the crown ether-modified micelles of the present embodiment, wherein steps S1 and S2 are the same as in Example 1, and steps S3 and S4 are:

[0064] S3, COOH-PEG 5000 -PCL modified to obtain alcohol ether-PEG 5000 -PCL

[0065] 0.2 g COOH-PEG 5000 -PCL was dissolved in 10ml of dichloromethane, then the catalyst was added into 6.18mg of dicyclohexylcarbodiimide (DCC) and 1.2mg of 4-dimethylaminopyridine (DMAP), the molar ratio of DCC:DMAP was 3:1 , and then add tetraethylene glycol monomethyl ether to make it and COOH-PEG 5000 -The molar ratio of PCL is 2:1, under stirring condition room temperature reaction 24h, freeze-drying after dialysis then, obtain the alcohol ether-PEG of 0.1763 grams 5000 -PCL, as another comparative example, replace tetraethylene glycol monomethyl ether with pentaethylene glycol monomethyl ether or hexaethylene glycol monomethyl ether, and other steps and reagents are the...

Embodiment 3

[0076] The preparation method of the crown ether modified micelle of the present embodiment comprises the following steps:

[0077] S1. Add 0.9g COOH-PEG 5000 -OH (carboxyl-polyethylene glycol 5000-hydroxyl) was dissolved in 10ml of toluene to obtain the first reaction solution with a concentration of 9mg / ml;

[0078] S2. Raise the temperature of the first reaction solution to 105°C, add catalysts 0.117g stannous isooctanoate and 0.99g caprolactone, react under slow stirring conditions for 20 hours, add 50ml of diethyl ether to the reaction product, and continue to use diethyl ether after centrifugal sedimentation Repeated washing three times, then freeze-dried to obtain carboxyl-polyethylene glycol 5000-polycaprolactone (COOH-PEG 5000 -PCL); the stannous isooctanoate is COOH-PEG 5000 13 wt% of -OH, the caprolactone used is COOH-PEG5000 110wt% of -OH;

[0079] S3, COOH-PEG 5000 Crown Ether Modification by -PCL to Obtain Crown Ether-PEG 5000 -PCL

[0080] 0.2g COOH-PEG 5...

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Abstract

The invention provides an unreported micelle. The micelle is a PEG 5000-PCL segmented copolymer micelle modified by crown ether. After COOH-PEG5000-PCL is synthesized through ring opening polymerization, crown ether is bonded to the COOH-PEG5000-PCL through an esterification reaction, and the molecular weight of the crown ether is about 10000. The required micelle is prepared by a solvent evaporation method, and finally, the cytotoxicity of the micelle to HeLa cells is determined by an MTT colorimetric method. The innovation of the micelle lies in that the complexing performance of crown etheron metal ions is utilized, and the metal ions in cells are complexed to destroy the tumor cell microenvironment so that the effect of inhibiting the activity of cancer cells is achieved.

Description

technical field [0001] The present invention relates to a kind of preparation field of polymer micelle, be specifically related to a kind of preparation method of the block copolymer micelle of crown ether modification. Background technique [0002] Cancer has long been a threat to human life, and conventional treatments such as chemotherapy can have serious side effects. Furthermore, the efficacy of traditional chemotherapy drugs is limited by nonspecific uptake and premature interpretation. In recent years, the emergence of nanomaterials has brought good news, the shortcomings of traditional treatment methods, and some nanomaterials have been approved for clinical use and polymers are increasingly used as people to encapsulate or bind anti-tumor drugs, including protein drugs Small molecule chemotherapeutics, nucleic acid drugs, and small interfering RNA (siRNA). Improve the pharmacokinetics of the drug and the accumulation at the tumor site, thereby reducing the side ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/07C08L67/04C08G63/664C08G63/85C08G63/91A61K9/107A61K31/335A61K47/60A61K47/69A61P35/00
CPCC08J3/07C08G63/664C08G63/912C08G63/823A61K9/1075A61K47/60A61K47/6907A61K31/335A61P35/00C08J2367/04
Inventor 丛海林于冰冯浩辉庞龙申有青
Owner QINGDAO UNIV
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