Anti-tumor prodrug using novel amphipathic hyperbranched polyesters as carrier and preparation method

An amphiphilic hyperbranched, anti-tumor technology, which is applied in the field of anti-tumor prodrugs and preparations, can solve the problems of difficult quality control of microspheres and microcapsules, unavoidable initial burst release, low production efficiency, etc., and achieve improved biocompatibility Sex, avoid toxic and side effects, enhance the effect of drug loading

Inactive Publication Date: 2009-07-08
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this regard, there are many research reports, but there are not many varieties for actual industrialization and clinical application. The main reason is that the production efficiency is very low, the quality control of microspheres and microcapsules is difficult, the stability is poor, and the initial burst release phenomenon is inevitable.

Method used

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  • Anti-tumor prodrug using novel amphipathic hyperbranched polyesters as carrier and preparation method
  • Anti-tumor prodrug using novel amphipathic hyperbranched polyesters as carrier and preparation method
  • Anti-tumor prodrug using novel amphipathic hyperbranched polyesters as carrier and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Add 9g of glycolic acid and 400ml of anhydrous ether into a 500ml single-necked flask, stir at room temperature until the glycolic acid is completely dissolved, then add catalyst, 4.56ml of tert-butyl bromide, and react at room temperature in the dark for 24 hours. Remove the precipitate in the reaction system by filtration, remove anhydrous ether by rotary evaporation, add dichloromethane to freeze and precipitate unreacted glycolic acid, extract with saturated aqueous solution of sodium bicarbonate, dissolve tert-butyl 2-hydroxyacetate in dichloromethane, and separate The organic phase and the aqueous phase were removed by rotary evaporation to remove dichloromethane to obtain 1.0 g of the product. The aqueous phase was adjusted to acidity with hydrochloric acid, then extracted with dichloromethane, and the methylene chloride was removed by rotary evaporation to obtain 1 g of 2-tert-butoxyacetic acid.

[0030] 2) In a 250ml single-necked flask, add 2g of glycolic ac...

Embodiment 2

[0036] 1) Add 11g of lactic acid and 400ml of anhydrous ether into a 500ml single-necked flask, stir at room temperature until the lactic acid is completely dissolved, then add catalyst, 4.56ml of tert-butyl bromide, and react at room temperature for 24 hours in the dark. Remove the precipitate by filtration, remove anhydrous ether by rotary evaporation, add dichloromethane to freeze and precipitate unreacted lactic acid, extract with saturated aqueous solution of sodium bicarbonate, dissolve the carboxyl group of lactic acid protected by tert-butyl group in dichloromethane, separate the organic phase and water phase, rotary evaporation to remove dichloromethane to obtain 1.0 g of the product, the aqueous phase was adjusted to acidity with hydrochloric acid, and then extracted with dichloromethane, rotary evaporation to remove dichloromethane to obtain 1 g of product tert-butyl-protected lactic acid hydroxyl.

[0037] 2) In a 250ml single-necked flask, add 2g of lactic acid wit...

Embodiment 3

[0040] Take 7 g of hyperbranched carboxylated polyester, 0.05 g of paclitaxel, 150 ml of tetrahydrofuran, 0.93 g of dicyclohexylcarbodiimide, and a catalytic amount of 4′4-dimethylaminopyridine, and react at room temperature for 24 hours. After the reaction, the urea salt was removed by filtration, and the tetrahydrofuran was concentrated. , slowly dropwise into anhydrous ether, let stand, and filter to obtain paclitaxel-loaded biodegradable amphiphilic hyperbranched polyester.

[0041] Other steps are the same as in Embodiment 1.

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Abstract

The invention provides an antitumor prodrug with novel amphiphilic hyper branched polyester as a carrier and a preparation method thereof. The novel biodegradable amphiphilic hyper branched polyester is constructed as being based on dimethylol propionic acid, an oligomer of glycolic acid or lactic acid and polyethyleneglycol or polyethylene glycol monomethyl ether. A peripheral functional group of the obtained hyper branched polymer is a hydroxyl group. The hyper branched polymer is reacted with estolide to be transformed into the hydroxyl group, the hydroxyl group is esterified with antitumor drug with the existence of condensing agent to obtain a prodrug of the antitumor drug. The introduction of the oligomer of the glycolic acid or the lactic acid or an alternative oligomer thereof improves the biocompatibility of drug carrier material, and the degrading speed of the oligomer in body is controlled by regulating the polymerization degree and the chemical composition of the oligomer to realize the action of controlling the release speed of the drug, so that the invention has very good drug sustained controlled release action and avoids the toxic side effect to normal cells caused by the burst release of the antitumor drug. The prodrug has an amphiphilic property, so that the prodrug can be made into a water-based preparation and improves the hydrophilicity of the antitumor drug greatly.

Description

Technical field: [0001] The invention relates to a novel amphiphilic hyperbranched polyester-carrier antitumor prodrug and a preparation method thereof. technical background: [0002] In recent years, the development of pharmaceutical dosage forms is inseparable from polymers. Polymer materials play two important roles in it: serving as drug carriers and imparting controlled release functions. Their physical forms are mainly microparticles, nanovesicles or microspheres, and gels. The basic technology for preparing micro and nano microspheres is microcapsule technology, especially emulsification technology and double emulsion technology. In this regard, there are many research reports, but there are not many varieties for actual industrialization and clinical application. The main reason is that the production efficiency is very low, the quality control of microspheres and microcapsules is difficult, the stability is poor, and the initial burst release phenomenon is inevita...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K45/00A61K47/34A61P35/00A61K31/337A61K31/4745A61K47/60
Inventor 张雪飞段谆谆钟冠群张海良
Owner XIANGTAN UNIV
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