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Synthesis method and use of cholic acid-modified polyamino acid block copolymer

A technology of block copolymers and polyamino acids, which is applied in the direction of medical preparations of non-active ingredients, emulsion delivery, pharmaceutical formulations, etc., can solve the problems of inability to deliver drugs to target sites, premature release of drugs, and insufficient micelles Stability and other issues, to achieve the effect of improving package efficiency, stability and efficiency

Active Publication Date: 2016-04-27
徐州康宇再生资源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the micelles formed by self-assembly of amphiphilic polymers are often not stable enough, dissociate when injected into the body due to a large amount of blood dilution, or interact with cells and biomolecules present in the blood, resulting in premature release of the drug, which cannot deliver the drug to target site

Method used

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  • Synthesis method and use of cholic acid-modified polyamino acid block copolymer
  • Synthesis method and use of cholic acid-modified polyamino acid block copolymer
  • Synthesis method and use of cholic acid-modified polyamino acid block copolymer

Examples

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Embodiment 1

[0040] Embodiment one, synthetic polymer PEG-pGlu (EDA-LA) 15 -CA under nitrogen protection, the CH 3 O-PEG-NH 2 (1.00g, 0.20mmol) was dissolved in dry DMF (4mL), added to a 50mL airtight reaction bottle, and BLG-NCA (1.05g, 4mmol) was added thereto, and the bottle was placed in a 40°C oil bath, Stir the reaction for 48 hours, settle with anhydrous ether, filter with a sand core funnel, and finally vacuum-dry for 24 hours to obtain a white solid, namely PEG-b-PBLG amphiphilic polymer. Yield: 85%.

[0041] Under nitrogen protection, CA (0.33g, 0.04mmol) was dissolved in dry THF (4mL) and 1mL of anhydrous acetonitrile, and then NHS (0.03g, 0.23mmol) and DCC (0.04g, 0.19mmol) Dissolve in anhydrous THF and add to the above solution, stir and react at room temperature for 18h; filter with a 0.45μm filter membrane, dissolve PEG-b-PBLG polymer (0.50g, 0.06mmol) in anhydrous THF, add In the reactor, add the above-mentioned filtered solution, react at room temperature for 24 hours,...

Embodiment 2

[0044] Embodiment two, synthetic polymer PEG-pGlu (EDA-LA) 26 -CA

[0045] Under nitrogen protection, the CH 3 O-PEG-NH 2 (0.50g, 0.10mmol) was dissolved in dry DMF (5mL), added to a 50mL airtight reaction bottle, and then BLG-NCA (0.71g, 2.70mmol) was added to it, and the bottle was placed in a 40°C oil bath , stirred for 48 hours, settled with anhydrous ether, filtered through a sand core funnel, and finally dried in vacuum for 24 hours to obtain a white solid, namely PEG-PBLG amphiphilic polymer. Yield: 84%

[0046] Under nitrogen protection, CA (0.13g, 0.34mmol) was dissolved in dry THF (3mL) and 1mL of anhydrous acetonitrile, added to the closed reactor, and NHS (0.05g, 0.40mmol) and DCC ( 0.07g, 0.34mmol) was dissolved in anhydrous THF and added to the above solution, stirred and reacted at room temperature for 18h; filtered with a 0.45μm filter membrane, and PEG-b-PBLG polymer (0.40g, 0.04mmol) was dissolved in THF in water was added to a closed reactor, and then t...

Embodiment 3

[0051] Example three, polymer PEG-pGlu (EDA-LA) 15 -CA nanomicelle preparation

[0052] Polymer PEG-LA nanomicelles were prepared by dialysis method. The specific process is: 1 mg polymer PEG-pGlu (EDA-LA) 15 -CA was dissolved in 1 mL of dimethyl sulfoxide, and 3 mL of secondary water was added dropwise thereto under stirring at 25°C. After the obtained solution was stirred for 05 h, it was loaded into a pre-prepared dialysis bag (MWCO3500), and dialyzed against deionized water for 24 h to obtain polymer nanomicelles.

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Abstract

The invention discloses a synthesis method and use of a cholic acid-modified polyamino acid block copolymer. A hydrophilic chain of the block copolymer is polyethylene glycol, a hydrophobic chain of the block copolymer is polyamino acid, the tail end of the polyamino acid is modified through micromolecular cholic acid, the side chain of the polyamino acid is a lipoyl group, and lipoic acid and an amino group of hydrophobic polyamino acid undergo a reaction to produce an amido bond. Through crosslinking of a self-assembled nanometer micelle of the cholic acid-modified polyamino acid block copolymer, a stable crosslinked reduction-sensitive polymer nanometer micelle is obtained so that the nanometer micelle is not easily damaged in vitro and in blood and nanometer micelle-coated drug stability is guaranteed. When the nanometer micelle enters a cancer cell, the nanometer micelle can be fast decrosslinked and dissociated and the coated drug can be fast released and produce high efficiency treatment effects. The cholic acid-modified polyamino acid block copolymer solves the problems of early release of a drug in vivo, low carrying efficiency and a slow release rate in cells.

Description

technical field [0001] The invention relates to a cholic acid-modified polyamino acid block copolymer, in particular to a polyamino acid and an amphiphilic block polymer in which cholic acid is modified at the end of the polyamino acid and the side chain is modified with lipoic acid. Background technique [0002] Polymer micelles are self-assembled in aqueous solution by amphiphilic polymers through intermolecular interactions (hydrogen bonds, hydrophilic / hydrophobic interactions, and van der Waals forces, etc.). It is an ordered molecular aggregate formed by self-assembly with hydrophobic groups as the inner core and hydrophilic groups as the outer shell. In addition to some common advantages of nano-drug carriers, polymer micelles also have superior physical and biochemical properties compared to other nano-carriers (such as liposomes and polymer nanoparticles): they have a clear core-shell structure , wherein the hydrophobic core part can be used to wrap hydrophobic drug...

Claims

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Application Information

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IPC IPC(8): C08G69/48C08G69/40C08J3/24C08J3/00A61K47/48A61K47/34A61K9/107
Inventor 李玉玲沈玉玲王赛杜百祥
Owner 徐州康宇再生资源科技有限公司
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