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Hydrophilic polymer the side chain of which is modified by lipoic acid and preparation and application thereof

A hydrophilic polymer and amphiphilic polymer technology, which is applied in the directions of non-active ingredients, such as medical preparations, educts, pharmaceutical formulations, etc. Efficiency, overcoming the effect of being easily leaked

Active Publication Date: 2011-09-28
BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no fully biodegradable, environmentally sensitive, reversibly cross-linked nano-drug carriers have been reported.

Method used

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  • Hydrophilic polymer the side chain of which is modified by lipoic acid and preparation and application thereof
  • Hydrophilic polymer the side chain of which is modified by lipoic acid and preparation and application thereof
  • Hydrophilic polymer the side chain of which is modified by lipoic acid and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment one, synthetic polymer Dex-LA (M n dextran =20kDa, DS=80%)

[0039] Under argon protection, lipoic acid (0.639g, 3.10mmol) was dissolved in 10mL of dichloromethane, added to a 50mL Schlenk vacuum-sealed bottle, and DCC dissolved in 5.0mL of dichloromethane was (0.384g, 1.86mmol) into a sealed bottle, put the bottle in an oil bath at 30°C, stir and react for 22 hours, cool, filter to remove the urea generated in the reaction, spin the filtrate, and remove the solvent to obtain lipoic anhydride .

[0040] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. In a 50mL three-necked flask, add dextran (0.25g, 1.55mmol AHG) dissolved in 19mL of dimethyl sulfoxide, and then add lipoic anhydride and dextran dissolved in 2mL of dimethyl sulfoxide in sequence under argon protection. 4-Dimethylaminopyridine (0.189g, 1.55mmol), the reactor was placed in an oil bath at 30°C, stirred and reacted for 48 hours, then precipitated i...

Embodiment 2

[0041] Embodiment two, synthetic polymer Dex-LA (M n dextran =20kDa, DS=20%)

[0042] Under argon protection, lipoic acid (0.255g, 1.24mmol) was dissolved in 10mL of dichloromethane, added to a 50mL Schlenk vacuum-sealed bottle, and DCC dissolved in 5.0mL of dichloromethane was dissolved under argon. (0.154g, 0.74mmol) into a sealed bottle, put the bottle in an oil bath at 30°C, stir and react for 22 hours, cool, filter to remove the urea generated in the reaction, spin the filtrate, and remove the solvent to obtain lipoic anhydride .

[0043] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. In a 50mL three-necked flask, add Dextran (0.25g, 1.55mmol AHG) dissolved in 19mL dimethyl sulfoxide, and then add lipoic anhydride and 4-dimethylamino dissolved in 2mL dimethyl sulfoxide in sequence under argon protection. Pyridine (0.076g, 0.62mmol), the reactor was placed in an oil bath at 30°C, stirred and reacted for 48 hours, then prec...

Embodiment 3

[0044] Embodiment three, synthetic polymer Dex-LA (M n dextran =70kDa, DS=40%)

[0045] Under argon protection, lipoic acid (0.352g, 1.71mmol) was dissolved in 10mL of dichloromethane, added to a 50mL Schlenk vacuum-sealed bottle, and DCC dissolved in 5.0mL of dichloromethane was (0.212g, 1.03mmol) into a sealed bottle, put the bottle in an oil bath at 30°C, stir and react for 22 hours, cool, filter to remove the urea generated in the reaction, spin the filtrate to obtain lipoic anhydride after removing the solvent .

[0046] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. In a 50mL three-necked flask, add Dextran (0.25g, 1.55mmol AHG) dissolved in 19mL dimethyl sulfoxide, and then add lipoic anhydride and 4-dimethylamino dissolved in 2mL dimethyl sulfoxide in sequence under argon protection. Pyridine (0.104g, 0.86mmol), the reactor was placed in an oil bath at 30°C, and after stirring and reacting for 48 hours, it was precipit...

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Abstract

The invention discloses a hydrophilic polymer the side chain of which is modified by lipoic acid and preparation and application thereof. The hydrophilic polymer the side chain of which is modified by lipoic acid is an amphipathic polymer; the main chain of the amphipathic polymer is an hydrophilic polymer, and the side chain is a lipoic acid radical; the lipoic acid radical and a hydroxide radical or an amino group in the hydrophilic polymer are condensed to form an ester bond or an acidamide bond; crosslinking can be carried out by nano particles formed by the self assembly of the amphipathic polymer to obtain stable crosslinking polymer nano particles with sensitive reduction, so that the nano particles are not easy to dissociate both outside cells and in blood, thereby ensuring the stability of drugs encapsulated by the nano particles; the nano particles rapidly relieve crosslinking to dissociate once entering tumor cells, and then the drugs rapidly release to generate the high-efficiency therapeutic effect. The deficiencies that the drugs are easy to leak, the carrying efficiency is low, the release speed in the cells is slow and the like are solved.

Description

technical field [0001] The invention relates to a modified hydrophilic polymer, in particular to a hydrophilic polymer whose side chain is modified with lipoic acid. Background technique [0002] Amphiphilic polymers can self-assemble in water to form polymer nanoparticles (Nanoparticles) by utilizing intermolecular interactions. Nanoparticles enter the body as a drug carrier, which can effectively reduce the phagocytosis of macrophages in the human reticuloendothelial system (RES), pass through the intercellular space, pass through the smallest capillaries and the blood-brain barrier (BBB) ​​in the human body, and be absorbed by cells and tissues . Nanoparticle drug carriers can control the release of drugs at targeted sites, reduce drug dosage, enhance drug efficacy and reduce drug toxicity. At the same time, the nanoparticle system can avoid the loss of drug activity, which is beneficial to the storage and transportation of drugs. Because of the many advantages of nano...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/36C08G65/48C08B37/02A61K47/34C08B37/08C08J3/24A61K47/10
CPCY02P20/141
Inventor 李玉玲刘兆忠周磊孟凤华钟志远
Owner BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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