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Preparation method and use of thioctic acid-modified polyethylene glycol-polyaminoacid block copolymer

A technology of lipoic acid and lipoyl group is applied in the field of modified amphiphilic triblock polymers to achieve the effect of overcoming easy leakage

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

However, so far, there are few reports on biodegradable, environmentally sensitive, reversibly cross-linked nano-drug carriers

Method used

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  • Preparation method and use of thioctic acid-modified polyethylene glycol-polyaminoacid block copolymer
  • Preparation method and use of thioctic acid-modified polyethylene glycol-polyaminoacid block copolymer
  • Preparation method and use of thioctic acid-modified polyethylene glycol-polyaminoacid block copolymer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment one, synthetic polymer PEG-pGlu(EDA-LA)-PPhe 20 (DP=10, PEG:Mn=5kDa)

[0037] Under nitrogen protection, the CH 3 O-PEG-NH 2 (0.3g, 0.06mmo) was dissolved in dry DMF (3mL), BLG-NCA (189.4mg, 0.72mmol) was added thereto, the system was warmed up to 35°C, and after stirring for 24h, Phe-NCA was added thereto ( 252.1mg, 1.32mmol) and DMF (6mL), continue to stir the reaction at 35°C for 24h. Settling in anhydrous ether gave PEG-PBLG-PPhe triblock polymer.

[0038] Under nitrogen protection, PEG-PBLG-PPhe (0.2 g, 0.182 mmol of benzyl functional group) was dissolved in dry DMF (4 mL) at 40 °C, to which was added distilled ethylenediamine (0.656 g, 10.92 mmol), after stirring and reacting for 36h, 10% acetic acid solution (12mL) was added dropwise to the system, dialyzed 3 times with 0.01M aqueous HCl solution, dialyzed 3 times with distilled water, and freeze-dried to obtain PEG-pGlu(EDA)-PPhe polymer Hydrochloride.

[0039] Under nitrogen protection, PEG-pGl...

Embodiment 2

[0040] Embodiment two, synthetic polymer PEG-pGlu (EDA-LA) 5 -PPhe 20 (DP=5, PEG:Mn=5kDa)

[0041] Under nitrogen protection, the CH 3 O-PEG-NH 2 (0.4g, 0.08mmo) was dissolved in dry DMF (4mL), BLG-NCA (126.2mg, 0.48mmol) was added thereto, the system was warmed up to 35°C, and after stirring for 24h, Phe-NCA was added thereto ( 336.2mg, 1.76mmol) and DMF (8mL), continue to stir the reaction at 35°C for 24h. Settling in anhydrous ether gave PEG-PBLG-PPhe triblock polymer.

[0042] Under nitrogen protection, PEG-PBLG-PPhe (0.3 g, 0.1945 mmol of benzyl functional groups) was dissolved in dry DMF (6 mL) at 40 °C, to which was added distilled ethylenediamine (0.58 g, 9.726 mmol), after stirring and reacting for 36h, 10% acetic acid solution (7.2mL) was added dropwise to the system, dialyzed 3 times with 0.01M aqueous HCl solution, dialyzed 3 times with distilled water, and freeze-dried to obtain PEG-pGlu(EDA)-PPhe polymer substance hydrochloride.

[0043] Under nitrogen pro...

Embodiment 3

[0044] Embodiment three, PEG-pGlu (EDA-LA) 10 -PPhe 20 (DP=10, PEG: Mn=5kDa) Nanomicelle Preparation

[0045] Polymer PEG-pGlu(EDA-LA) 10 -PPhe nanomicelles were prepared by a dialysis method. The specific process is: 2 mg polymer PEG-pGlu (EDA-LA) 10 - PPhe was dissolved in 1 mL of dimethyl sulfoxide, and 5 mL of deionized water was added dropwise thereto under stirring at 25°C. After the obtained solution was stirred for 1 h, it was put into a pre-prepared dialysis bag (SPECTRA / POR, MWCO: 3500), and dialyzed with deionized water for 24 h. The nanomicelle is 130.2 nanometers, and the particle size distribution is 0.188.

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Abstract

The invention discloses a preparation method and use of a thioctic acid-modified polyethylene glycol-polyaminoacid amphiphilic triblock copolymer. A hydrophilic chain of the amphipathic triblock polymer is polyethylene glycol, a middle hydrophobic chain segment of the amphipathic triblock polymer is poly(benzyl glutamate), a tail hydrophobic chain segment of the amphipathic triblock polymer is polyphenylalanine and the side chain of the middle chain segment is modified through thioctic acid. The amphipathic triblock polymer is self-assembled in water to form a polymer nanometer micelle with polyethylene glycol as an outer crown, thioctic acid-modified poly(benzyl glutamate) as a middle shell and polyphenylalanine as an inner core. Through crosslinking of the nanometer micelle, the stable reduction-sensitive shell crosslinked nanometer micelle is obtained so that the nanometer micelle is not easily dissociated in vitro and in blood and thus stability of a nanometer micelle-coated drug is guaranteed. When the nanometer micelle enters a tumor cell, the nanometer micelle can be fast crosslinked and dissociated so that the drug can be fast released and produces high treatment effects. The amphipathic triblock polymer solves the problems of drug leakage in vivo, low conveying efficiency and slow release in cells.

Description

technical field [0001] The invention relates to a modified amphiphilic three-block polymer, in particular to an amphiphilic three-block polymer whose middle hydrophobic segment side chain is modified with lipoic acid. Background technique [0002] Due to the enhanced penetration and retention (EPR) effect of nanocarriers, targeted and controlled release of anticancer drugs, various nanocarriers have been developed to improve the efficacy of cancer chemotherapy in recent years. As a nanocarrier, polymer micelles are widely used in drug delivery due to their excellent properties: prolonging drug circulation time, improving drug solubility, and enhancing EPR effect to passively target tumor sites. Amphiphilic polymers can self-assemble in water to form polymer nanomicelles (Micelles) through intermolecular interactions. As a drug carrier, nanomicelles enter the body, which can effectively reduce the phagocytosis of macrophages in the human reticuloendothelial system (RES), pas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48C08G69/40C08J3/24C08J3/00A61K47/34A61K9/107
Inventor 李玉玲王赛沈玉玲杜百祥
Owner 徐州康宇再生资源科技有限公司
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