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Responsive cross-linked polymer micelle based on multiple hydrogen bond interactions, and preparation method and application thereof

A technology of cross-linked polymers and multiple hydrogen bonds, which is applied in the direction of non-active ingredient medical preparations, pharmaceutical formulas, emulsion delivery, etc., and can solve the problems of premature release of carried drugs, low targeting of cancer cells, and slow release speed and other issues to achieve good reproducibility, uniform stability, and increased stability

Active Publication Date: 2019-11-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, during the transport of polymer micelles in the body, there will be a phenomenon of sudden drug release, which leads to the problem of premature release of the drug and low targeting of cancer cells.
After the burst release, due to the diffusion of the drug, its release rate becomes very slow, and there is certain drug toxicity to normal cells

Method used

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  • Responsive cross-linked polymer micelle based on multiple hydrogen bond interactions, and preparation method and application thereof
  • Responsive cross-linked polymer micelle based on multiple hydrogen bond interactions, and preparation method and application thereof
  • Responsive cross-linked polymer micelle based on multiple hydrogen bond interactions, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] 1. Dissolve CTA (7.2800g, 20mmol), dry mPEG (10.0000g, 5mmol) and DMAP (0.2440g, 2mmol) in 60mL CH 2 Cl 2 After being completely dissolved, EDC (1.9170g, 10mmol) was added, reacted at 25°C for three days, and the insoluble matter was removed. After concentration, the solution was precipitated twice in ether to obtain a light yellow solid. The resulting solid was dissolved in 80 mL CH 2 Cl 2 In, with saturated Na 2 CO 3 The aqueous solution was washed three times, and the obtained organic phase was dried over anhydrous sodium sulfate for 12 hours. Filtration, after most of the solvent is removed by rotary evaporation, precipitation in excess glacial ether, to obtain light yellow powder solid, namely the macromolecular chain transfer agent (mPEG) shown in formula I-1 39 -CTA).

[0043] 2. The mPEG 39 -CTA (0.7002g, 0.3mmol), DMAEMA (1.5700g, 10mmol), UPy-HEMA (0.4367g, 1.1mmol) and AIBN (0.0164g, 0.1mmol) were added to a 50mL Shrek tube, and 5mL DMSO wa...

Embodiment 2

[0047]

[0048] 1. Dissolve CTA (6.552g, 18mmol), dry mPEG (4.0000g, 2mmol) and DMAP (0.2440g, 2mmol) in 60mL CH 2 Cl 2 After being completely dissolved, EDC (1.5336g, 8mmol) was added, and the insoluble matter was removed after three days of reaction at 25°C. The solution was concentrated and precipitated twice in ether to obtain a light yellow solid. The resulting solid was dissolved in 80 mL CH 2 Cl 2 In, with saturated Na 2 CO 3 The aqueous solution was washed three times, and the obtained organic phase was dried over anhydrous sodium sulfate for 12 hours. Filtrate, after rotary evaporation removes most of solvent, precipitate in excess glacial ether, obtain pale yellow powder solid, the macromolecular chain transfer agent (mPEG) shown in formula I-2 32 -CTA).

[0049] 2. The mPEG 32 -CTA (0.4668g, 0.2mmol), DMAEMA (1.4444g, 9.2mmol), UPy-HEMA (0.3176g, 0.8mmol) and AIBN (0.0164g, 0.1mmol) were added to a 50mL Shrek tube, and 5mL DMSO was added to make It was di...

Embodiment 3

[0053]

[0054] 1. Dissolve CTA (8.008g, 22mmol), dry mPEG (6.0000g, 3mmol) and DMAP (0.2440g, 2mmol) in 60mL CH 2 Cl 2 After being completely dissolved, EDC (2.3004g, 12mmol) was added, reacted at 25°C for three days, and the insoluble matter was removed. After concentration, the solution was precipitated twice in ether to obtain a light yellow solid. The resulting solid was dissolved in 80 mL CH 2 Cl 2 In, with saturated Na 2 CO 3 The aqueous solution was washed three times, and the obtained organic phase was dried with anhydrous sodium sulfate for 12 hours. Filtration, after rotary evaporation removes most of solvent, precipitate in excess glacial ether, obtain light yellow powder solid, the macromolecular chain transfer agent (mPEG) shown in formula I-3 35 -CTA).

[0055] 2. The mPEG 35 -CTA (0.2334g, 0.1mmol), DMAEMA (1.4915g, 9.5mmol), UPy-HEMA (0.1985g, 0.5mmol) and AIBN (0.0164g, 0.1mmol) were added to a 50mL Shrek tube, and 5mL DMSO was added to make It was...

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Abstract

The invention discloses a responsive cross-linked polymer micelle based on multi-hydrogen bond interaction as well as a preparation method and an application thereof. The structural formula of the micelle is as follows: x is an integer of 20-50, y1 is an integer of 80-110, and y2 is an integer of 3-15.According to the invention, the amphiphilic block copolymer is prepared by using dimethylaminoethyl methacrylate as a hydrophilic chain and a ureidopyrimidinone group with multiple hydrogen bond interactions as a hydrophobic chain through a simple one-pot method; the polymer is self-assembled inwater to form a uniform and stable core cross-linked micelle, and then the core cross-linked micelle and N,N'-bis(bromoacetyl)cystamine are subjected to a cross-linking reaction to prepare the polymer. The responsive cross-linked polymer micelle based on multiple hydrogen bond interaction is used as a drug delivery carrier to encapsulate nile red; the result shows that the responsive cross-linkedpolymer micelle has good stability and reasonable controlled release ability, has great potential in drug delivery, and has huge application prospect.

Description

technical field [0001] The invention belongs to the technical field of stimuli-responsive polymer materials, and in particular relates to a responsive cross-linked polymer micelle based on multiple hydrogen bond interactions, as well as a preparation method and application of the polymer micelle. Background technique [0002] Life forms in nature have undergone hundreds of millions of years of evolution, and have almost perfected all processes of intelligent control. Learning from nature is a source of inspiration for humans to develop new materials for artificial intelligence. DNA in organisms uses double hydrogen bonds and triple hydrogen bonds to self-replicate and store information, and uses this relatively strong but reversible effect to ensure the accuracy of genetic information replication. In recent years, many researchers at home and abroad have devoted themselves to exploring and studying multiple hydrogen bond units to construct supramolecular assemblies, and sti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/34C08F220/36C08J3/24C08J3/02A61K9/107A61K47/34
CPCA61K9/1075A61K47/34C08F220/34C08F220/36C08F293/005C08F2438/03C08J3/02C08J3/24
Inventor 雷忠利周琪杨红
Owner SHAANXI NORMAL UNIV
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