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Thioctic acid-modified hydrophilic polymer for side chain

A technology of hydrophilic polymer and amphiphilic polymer, applied in the field of modified hydrophilic polymer, can solve problems such as environmentally sensitive nano-drug carriers, improve the encapsulation efficiency, improve the stability, and overcome the easy leakage Effect

Active Publication Date: 2011-10-12
JIANGSU SENRAN CHEM +1
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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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  • Thioctic acid-modified hydrophilic polymer for side chain
  • Thioctic acid-modified hydrophilic polymer for side chain
  • Thioctic acid-modified hydrophilic polymer for side chain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment one, synthetic polymer Dex-LA ( M ndextran =20 kDa, DS = 80%)

[0040] Under the protection of argon, dissolve lipoic acid (0.639 g, 3.10 mmol) in 10 mL of dichloromethane, add it into a 50 mL Schlenk vacuum-sealed bottle, and dissolve DCC in 5.0 mL of dichloromethane under argon (0.384g, 1.86 mmol) 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 .

[0041] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. Add dextran (0.25 g, 1.55 mmol AHG) dissolved in 19 mL of dimethyl sulfoxide to a 50 mL three-neck flask. Under argon protection, add lipoic anhydride and 2 mL of dimethyl sulfoxide 4-Dimethylaminopyridine (0.189g, 1.55 mmol), the reactor was placed in an oil bath at 30°C, and after stirring for 48 hours, it was precipitated into cold eth...

Embodiment 2

[0042] Embodiment two, synthetic polymer Dex-LA ( M ndextran =20 kDa, DS = 20%)

[0043] Under the protection of argon, dissolve lipoic acid (0.255 g, 1.24 mmol) in 10 mL of dichloromethane, add it to a 50 mL Schlenk vacuum-sealed bottle, and dissolve DCC in 5.0 mL of dichloromethane under argon Add (0.154g, 0.74 mmol) 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, and spin the filtrate to obtain lipoic anhydride after removing the solvent .

[0044] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. Add Dextran (0.25 g, 1.55 mmol AHG) dissolved in 19 mL of dimethyl sulfoxide to a 50 mL three-necked flask, and then add lipoic anhydride and 4-dimethylamino dissolved in 2 mL of dimethyl sulfoxide in sequence under argon protection Pyridine (0.076g, 0.62 mmol), the reactor was placed in an oil bath at 30°C, and after stirring for 4...

Embodiment 3

[0045] Embodiment three, synthetic polymer Dex-LA ( M ndextran =70 kDa, DS = 40%)

[0046] Under the protection of argon, dissolve lipoic acid (0.352 g, 1.71 mmol) in 10 mL of dichloromethane, add it into a 50 mL Schlenk vacuum-sealed bottle, and dissolve DCC in 5.0 mL of dichloromethane under argon Add (0.212g, 1.03 mmol) 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 .

[0047] The lipoic anhydride obtained above was added to 3 mL of anhydrous-treated dimethyl sulfoxide. Add Dextran (0.25 g, 1.55 mmol AHG) dissolved in 19 mL of dimethyl sulfoxide to a 50 mL three-necked flask, and then add lipoic anhydride and 4-dimethylamino dissolved in 2 mL of dimethyl sulfoxide in sequence under argon protection Pyridine (0.104g, 0.86 mmol), the reactor was placed in an oil bath at 30°C, and after stirring for 4...

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Abstract

The invention discloses a thioctic acid-modified hydrophilic polymer for a side chain, a preparation method thereof and application thereof. The thioctic acid-modified hydrophilic polymer is an amphiphilic polymer, wherein the main chain of the amphiphilic polymer is the hydrophilic polymer; the side chain is a thioctic acyl; and the thioctic acyl is condensed with a hydroxyl or an amido in the hydrophilic polymer to form an ester bond or an amido bond. Nano particles formed by self-assembly of the amphiphilic polymer can be cross-linked to obtain stable cross-linked polymer nano particles which are sensitive to reduction, so the nano particles are not easy to disaggregate outside cells or in blood and then a medicament wrapped by the nano particles is ensured to be stable; once entering a tumor cell, the nano particles are quickly de-cross-linked to be disaggregated, so the medicament are quickly released and a high-efficiency treatment effect is achieved; and the disadvantages of easiness in leakage of the medicament in vivo, low carrying efficiency, slow release in cells and the like are overcome.

Description

[0001] This application is a divisional application of the Chinese invention patent application with application number 200910181922.6. The filing date of the original application is: July 23, 2009, the application number is: 200910181922.6, and the name of the invention is: hydrophilic side chain modified with lipoic acid Polymers and their preparation and applications. technical field [0002] The invention relates to a modified hydrophilic polymer, in particular to a hydrophilic polymer whose side chain is modified with lipoic acid. Background technique [0003] 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 ...

Claims

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Application Information

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IPC IPC(8): C08B37/02C08B37/08
Inventor 钟志远李玉玲刘兆忠周磊孟凤华
Owner JIANGSU SENRAN CHEM
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