Preparation of block copolymer with quadruple responsiveness and application thereof

A technology of block copolymers and block polymers, which is applied in the direction of medical preparations with non-active ingredients, medical preparations containing active ingredients, and photo-splitting of drugs in the body, which can solve the problem of insufficient penetration and low release efficiency , Poor tissue permeability and other issues

Inactive Publication Date: 2017-06-27
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many studies based on polydimethylaminoethyl methacrylate, such as PDMS-b-PDMAEMA (Car A, Baumann P, Duskey J T, et al.[J].Biomacromolecules,2014,15(9):3235-45 .), the polymer does not have photoresponsiveness, and cannot realize the fixed-point release of the drug; another example is the polydimethylaminoethyl methacrylate functionalized by pyrene, perylene, azobenzene, spiropyran and nitrobenzene. Although the preparation and self-assembly research of esters can achieve fixed-point release through light stimulation, the problem is that the release efficiency of guest molecules is low, and the ultraviolet light used to stimulate micelles, visible light has side effects on organisms, and it is easy to burn tissues , poor tissue permeability, compared with these photoresponsive molecules, 2-diazo-1-naphthol-5-sulfonyl chloride not only has ultraviolet photoresponsiveness but also has the characteristics of near-infrared photoresponse. In-depth, there is no good combination of the excellent characteristics of the above two materials

Method used

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  • Preparation of block copolymer with quadruple responsiveness and application thereof
  • Preparation of block copolymer with quadruple responsiveness and application thereof
  • Preparation of block copolymer with quadruple responsiveness and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]Step 1: Preparation of polyethylene glycol-block-polydimethylaminoethyl methacrylate: 8 mL of polymerizable monomer dimethylaminoethyl methacrylate, 200 mg of macroinitiator PEG-Br, and 14 mg of catalyst were brominated Cuprous metal was dissolved in 4 mL of dry tetrahydrofuran, placed in a Schlenk flask, and 20uL of tris(2-dimethylaminoethyl)amine was injected into the Schlenk flask with a pipette gun, and stirred for 30 minutes until complete Dissolve, nitrogen gas for 60 minutes to remove oxygen, after seven cycles of "freezing-pumping-thawing", put it in an oil bath at 55 degrees Celsius for 10 hours, and pass the product through a chromatographic column equipped with neutral alumina to remove the catalyst , and petroleum ether precipitated 4 times, and dried in a vacuum oven at 55 degrees Celsius for 24 hours to obtain a block polymer polyethylene glycol-block-polydimethylaminoethyl methacrylate.

[0031] Step 2: Prepare the polymer: According to the budgeted grafti...

Embodiment 2

[0035] Step 1: Preparation of polyethylene glycol-block-polydimethylaminoethyl methacrylate: polymerizable monomer dimethylaminoethyl methacrylate, macroinitiator PEG-Br, and catalyst cuprous bromide are dissolved In dry tetrahydrofuran, place in a Schlenk flask, use a pipette gun to inject tris(2-dimethylaminoethyl)amine into the Schlenk flask, stir for 40 minutes until completely dissolved, and pass nitrogen gas for about Oxygen was removed for 40 minutes, after six "freezing-pumping-thawing" cycles, it was placed in an oil bath at 65 degrees Celsius for 8 hours, and the product was passed through a chromatographic column equipped with neutral alumina to remove the catalyst. The ether was precipitated 3 times, the upper liquid was removed to remove the remaining deposited solid, and the solid was dried in a vacuum oven at 50 degrees for 16 hours to obtain the block polymer polyethylene glycol-block-polymethacrylic acid dimethylamino ethyl ester. The molar ratio of dimethyla...

Embodiment 3

[0039] Step 1: Preparation of polyethylene glycol-block-polydimethylaminoethyl methacrylate: 10 mL of polymerizable monomer dimethylaminoethyl methacrylate, 210 mg of macroinitiator PEG‐Br, and 30 mg of catalyst were brominated Dissolve cuprous in 7mL of dry tetrahydrofuran, place in a Schlenk flask, inject 40uL tris(2-dimethylaminoethyl)amine into the Schlenk flask with a pipette gun, and stir for 50 minutes until complete Dissolve, nitrogen gas for 30 minutes to remove oxygen, after eight cycles of "freezing-pumping-thawing", put it in an oil bath at 75 degrees Celsius for 6 hours, and pass the product through a chromatographic column equipped with neutral alumina to remove the catalyst , and petroleum ether precipitated 3 times, and dried in a vacuum oven at 50 degrees for 24 hours to obtain a block polymer polyethylene glycol-block-polydimethylaminoethyl methacrylate.

[0040] Step 2: Prepare the polymer: according to the budgeted graft ratio, add 0.6g of 2-diazo-1-naphtho...

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Abstract

The invention provides preparation of a block copolymer micelle with quadruple responsiveness and application thereof. The preparation specifically comprises the following steps: preparing a polyethylene glycol-block-polymethylacrylic acid dimethylamino ethyl ester (PEG-b-PDMAEMA) block copolymer with a macroinitiator (mPEG-Br) and a methylacrylic acid dimethylamino ethyl ester monomer by atom transfer radical polymerization; grafting 2-diazo-1-naphthol-5-sulfonyl chloride on the polyethylene glycol-block-polymethylacrylic acid dimethylamino ethyl ester (PEG-b-PDMAEMA) block copolymer by a quaternization reaction, so as to obtain the amphiphilic block copolymer with quadruple responsiveness of near-infrared light, ultraviolet light, pH and temperature. The polymer can be self-assembled in water to form nano-particles capable of wrapping hydrophobic micromolecules such as coumarin 102; due to single or synergistic stimulation of near-infrared light 808nm, ultraviolet light 365nm, pH and temperature, the appearance of the micelle is changed, so that loaded micromolecules are released. The micelle provided by the invention has quadruple responsiveness of near-infrared light, ultraviolet light, pH and temperature and has wide application prospect in the aspect of controlling drug release.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to the preparation and application of a four-fold responsive block polymer micelle to near-infrared light, ultraviolet light, pH and temperature. Background technique [0002] In recent years, researchers have been devoting themselves to research in the field of controlled drug release, and have made some progress. Among them, responsive polymer micelles are widely used due to their rapid response to external environmental stimuli, but there are still some problems. At present, most micelles have low biocompatibility, slow release efficiency, low loading rate, and are single-stimuli responses. , such as pH, temperature, ionic strength, magnetic field, etc., many of which are harmful to organisms. In contrast, light stimulation has more advantages, such as controlled release at a fixed point, without contacting the human body. [0003] Polydimethylaminoethyl methacrylate has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F8/44C08J3/02C08J3/03A61K41/00A61K9/107A61K47/34C08L53/00
CPCA61K9/0009A61K9/1075A61K41/0042A61K47/34C08F8/44C08F293/00C08F2810/50C08J3/02C08J3/03C08J2353/00
Inventor 王国杰李清伟曹自权
Owner UNIV OF SCI & TECH BEIJING
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