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A multi-acid-sensitive anti-tumor drug-loaded micelle containing zwitterions and its preparation method and application

A zwitterionic, acid-sensitive technology, applied in the field of multiple acid-sensitive anti-tumor drug-loaded micelles and its preparation, can solve the problems that nanoparticles cannot respond quickly, and it is difficult to reach the therapeutic concentration of drugs, and achieve low toxic and side effects and high drug loading The effect of volume, high sensitivity and responsiveness

Inactive Publication Date: 2019-09-20
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is only one sensitive bond in most nanomaterials. Nanoparticles cannot respond with high sensitivity and rapid response in the tumor microenvironment to achieve drug burst release, and it is difficult to reach the therapeutic concentration of the drug to achieve anti-tumor effect.

Method used

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  • A multi-acid-sensitive anti-tumor drug-loaded micelle containing zwitterions and its preparation method and application
  • A multi-acid-sensitive anti-tumor drug-loaded micelle containing zwitterions and its preparation method and application
  • A multi-acid-sensitive anti-tumor drug-loaded micelle containing zwitterions and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: Preparation of 2,2-bis(acryloyloxy-1-ethoxy)propane

[0054] First, mix hydroxyethyl acrylate and 2,2-dimethoxypropane in a molar ratio of 2:1, add benzene and p-toluenesulfonic acid, and distill the benzene-methanol azeotrope under the reaction conditions of 58°C out to obtain the initial product. The obtained primary product was purified by silica gel column chromatography, eluted with a mixed solvent of n-hexane and dichloroethane (1:1), and the eluent was removed by rotary evaporation to obtain a colorless oily liquid. After the product ADA.

Embodiment 2

[0055] Example 2: Preparation of Carboxybetaine Methacrylate (CBMA)

[0056] Dissolve 0.11 mmol of 2-(dimethylamino)ethyl methacrylate in 50 mL of anhydrous acetone under vigorous stirring, and slowly dissolve 0.14 mmol of β-propiolactone in 10 mL of anhydrous acetone under nitrogen protection Add dropwise to the above solution. Under the protection of nitrogen, the reaction was carried out at 4° C. for 5 h to obtain a white powder. Afterwards, the obtained white powder was washed successively with anhydrous acetone and anhydrous ether, and dried in a vacuum oven to obtain a white powder product.

Embodiment 3

[0057] Example 3: Preparation of polycarboxybetaine methacrylate (pCBMA)

[0058] Use ATRP method (atom transfer radical polymerization) reaction to prepare polycarboxylate betaine methacrylate, use the product synthesized in Example 2 as a reaction monomer, and use ethyl 2-bromoisobutyrate as an initiator , with 1,1,4,7,10,10-hexamethyltriethylenetetramine as a ligand, put into a dry branch bottle at a molar ratio of monomer:initiator:ligand=16.6:1:2 In the process, three vacuum-nitrogen cycles were performed to ensure the oxygen-free environment of the reaction system. Methanol:N,N-dimethylformamide (1:1) was injected into the reaction system with a syringe as a solvent, and cuprous bromide was added after three vacuum-nitrogen cycles. The reaction system was sealed and reacted at 60 °C for 24 h. The reaction system was communicated with air to terminate the reaction. The initial reaction product obtained is dialyzed in neutral water with a 500-1000 molecular weight cut-o...

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Abstract

The invention discloses a zwitter-ion-contained multiple acid-sensitive anti-tumor drug-loading micelle, and a preparation method and an application thereof, and belongs to the field of biological materials. The zwitter-ion-contained multiple acid-sensitive anti-tumor drug-loading micelle comprises a zwitter-ion hydrophilic shell and a lyophobic core containing two acid-sensitive bonds. The method includes the steps: separating methanol from hydroxyethyl acrylate and 2,2-dimethoxypropane and synthesizing 2,2-di(acryloyloxy-1-oxethyl) propane by an alcohol exchange method; connecting open-loop beta-propiolactone with 2-(dimethylamino) ethyl methacrylate to synthesize carboxybetaine methacrylate; obtaining a carboxybetaine methacrylate monomer polymer by an atom transfer free radical polymerization method; synthesizing triblock amphiphilic polymers by the atom transfer free radical polymerization method and a Michael addition one-pot method, and preparing the drug-loading nano-micelle by an ultrasonic drop method and a dialysis method. By aid of the drug-loading micelle, anti-tumor effects of chemotherapeutic drugs can be improved.

Description

technical field [0001] The invention belongs to the field of biological materials, in particular to a zwitterion-containing multiple acid-sensitive anti-tumor drug-loaded micelle, a preparation method and application thereof. [0002] technical background [0003] According to the statistics of the World Health Organization in 2013, tumors have become one of the major diseases threatening human health. Chemotherapy is currently one of the most commonly used and effective methods for clinical treatment of tumors. However, due to the lack of specific selection between tumor cells and normal cells, chemotherapy drugs also have strong toxicity, resulting in serious complications during the treatment process. toxic side effect. The emergence of nano-drug loading system has solved these problems well. Nanoparticles within a certain particle size range can use the enhanced penetration and retention effect (EPR effect) of tumor sites to enrich solid tumor sites through passive targ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/02C08G73/06A61K9/107A61K47/34A61K31/704A61P35/00
Inventor 顾忠伟马瑾易强英康珂
Owner SICHUAN UNIV
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