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Folate-polyethylene glycol-polylactic acid segmented copolymer micelle encapsulated with hydrophobic anticancer drug and preparation method of segmented copolymer micelle

A technology of block copolymer and polyethylene glycol, which can be used in anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., can solve the problems such as no, and achieve the effects of good stability and good drug-carrying effect.

Inactive Publication Date: 2014-01-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Chinese Academy of Sciences and the Chengdu Institute of Organic Chemistry have used this material to prepare blank microspheres and encapsulate membrane proteins and albumin, which proves that the copolymer can better encapsulate proteins; however, there is no such copolymer encapsulation card after consulting the literature Reports on Experimental Research on Betabine

Method used

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  • Folate-polyethylene glycol-polylactic acid segmented copolymer micelle encapsulated with hydrophobic anticancer drug and preparation method of segmented copolymer micelle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0029] (1) Diaminopolyethylene glycol (NH 2 -PEG-NH 2 ) preparation

[0030] Dissolve 15g of polyethylene glycol-4000 in 50mL of dichloromethane solution, add 1.25g of triethylamine, dropwise add 7.5g of p-toluenesulfonyl chloride in 25mL of dichloromethane solution at 0°C, and react at room temperature for 6h. The solution was rotovaped and dropped into anhydrous ether. The crude product of polyethylene glycol-p-toluenesulfonate was obtained by suction filtration, and then excess p-toluenesulfonyl chloride was removed through repeated dissolution and precipitation, and dried in a vacuum oven for 48 hours to obtain polyethylene glycol-p-toluenesulfonate Pure.

[0031] Put 10 g of the obtained polyethylene glycol-p-toluenesulfonate pure product and 20 mL of ammonia water with a volume fraction of 25% in a pressure-resistant container, and react in a closed manner at 100 ° C for 8 h, cool to room temperature, and extract with dichloromethane. Sodium hydroxide was added to t...

Embodiment example 2

[0045] Preparation of folic acid-polyethylene glycol-polylactic acid block copolymer micelles encapsulating capecitabine:

[0046] (1) Diaminopolyethylene glycol (NH 2 -PEG-NH 2 ) preparation

[0047] Dissolve 20g of polyethylene glycol-4000 in 50mL of dichloromethane solution, add 1.54g of triethylamine, dropwise add 8g of p-toluenesulfonyl chloride in 23mL of dichloromethane solution at 2°C, and react at room temperature for 7h. The solution was rotovaped and dropped into anhydrous ether. The crude product of polyethylene glycol-p-toluenesulfonate was obtained by suction filtration, and the excess p-toluenesulfonyl chloride was removed through repeated dissolution and precipitation, and dried in a vacuum oven for 54 hours to obtain polyethylene glycol-p-toluenesulfonate Pure.

[0048] 10 g of the obtained polyethylene glycol-p-toluenesulfonate pure product and 17.5 mL of ammonia water with a volume fraction of 28% were placed in a pressure-resistant container, and the r...

Embodiment example 3

[0062] Preparation of folic acid-polyethylene glycol-polylactic acid block copolymer micelles encapsulating capecitabine:

[0063] (1) Diaminopolyethylene glycol (NH 2 -PEG-NH 2 ) preparation

[0064]Dissolve 25g of polyethylene glycol-4000 in 50mL of dichloromethane solution, add 1.786g of triethylamine, add dropwise 21mL of dichloromethane solution containing 8.33g of p-toluenesulfonyl chloride at 0°C, and react at room temperature for 8h . The solution was rotovaped and dropped into anhydrous ether. The crude product of polyethylene glycol-p-toluenesulfonate was obtained by suction filtration, and then excess p-toluenesulfonyl chloride was removed through repeated dissolution and precipitation, and dried in a vacuum oven for 60 hours to obtain polyethylene glycol-p-toluenesulfonate Pure.

[0065] Put 10 g of the obtained polyethylene glycol-p-toluenesulfonate pure product and 15 mL of ammonia water with a volume fraction of 30% in a pressure-resistant container, and r...

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Abstract

The invention discloses a folate-polyethylene glycol-polylactic acid segmented copolymer micelle encapsulated with a hydrophobic anticancer drug and a preparation method of the segmented copolymer micelle. The preparation method comprises the steps as follows: bis-amino polyethylene glycol polymer is prepared firstly; mono amino polyethylene glycol tert-butyl ester polymer is prepared by the bis-amino polyethylene glycol polymer; the mono amino polyethylene glycol tert-butyl ester polymer is cross-linked with lactide to obtain tert-butoxy acylamino polyethylene glycol-polylactic acid polymer, and the tert-butoxy acylamino polyethylene glycol-polylactic acid polymer reacts with trifluoroacetic acid to obtain amino-terminated polyethylene glycol-polylactic acid polymer; and the amino-terminated polyethylene glycol-polylactic acid polymer and activated folate react away from light to obtain the folate-polyethylene glycol-polylactic acid polymer. The compound has hydrophilia , biocompatibility and water solubility of the hydrophobic segment, material absorption and cell adhesion of protein can be reduced, the circulation time of the drug in blood is prolonged, and the formed copolymer has modificability; a tumor target compound with low molecular weight and hydrophilic polyethylene glycol-4000 segmer are bonded to form a hydrophilic segment; and the hydrophobic segment is polylactic acid, and the hydrophobic anticancer drug is embedded into the hydrophobic segment, so that the toxic and side effects are reduced.

Description

technical field [0001] The invention relates to the technical field of block copolymer micelles, in particular to a folic acid-polyethylene glycol-polylactic acid block copolymer micelles encapsulating hydrophobic anticancer drugs and a preparation method thereof. Background technique [0002] Commonly used hydrophobic drugs are doxorubicin and capecitabine. Among them, Capecitabine (Capecitabine) was first launched in Switzerland in 1998 and was developed by Swiss Hoffmann-LaRoche Company. It is a new type of oral flucytosine nucleoside analogue, it is the prodrug of 5-Fu, it is non-toxic, and it is metabolized into pentafluorouracil (5-Fu) under the action of enzymes in vivo, it can be released in the body Selecting tumor activation, the concentration of 5-Fu in the tumor tissue is high, which reduces the systemic toxicity of 5-Fu. However, in clinical use, in order to reduce the impact of anti-tumor drugs on cells, intravenous injection is generally used to maintain t...

Claims

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Application Information

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IPC IPC(8): A61K47/36A61K9/107A61K47/22A61K31/7068A61K31/704A61P35/00
Inventor 魏坤魏诗琪邹芬
Owner SOUTH CHINA UNIV OF TECH
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