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Ph-redox double sensitive amphiphilic polymer and preparation method thereof

An amphiphilic polymer and sensitive technology, applied in the field of polymers, can solve the problems of poor delivery stability, poor targeting, and poor controllability, and achieve good redox sensitivity and enrichment effects

Inactive Publication Date: 2014-03-05
XIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a pH-redox dual-sensitive amphiphilic polymer, which solves the problems of poor controllability, poor delivery stability and targeting when the existing amphiphilic polymer is used as a drug carrier

Method used

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  • Ph-redox double sensitive amphiphilic polymer and preparation method thereof
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  • Ph-redox double sensitive amphiphilic polymer and preparation method thereof

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preparation example Construction

[0032] The preparation method of the above-mentioned pH-redox double-sensitive amphiphilic polymer, the specific steps are as follows:

[0033] Step 1, add bis(2-hydroxyethyl) disulfide to a round bottom flask, add dichloromethane, triethylamine and methacryloyl chloride under ice bath conditions, then seal the system and place it under magnetic force at 0°C After stirring for 3 to 5 hours, washing and extraction were carried out in sequence, and the organic extract was washed with anhydrous Na 2 SO 4 After drying for 8-14 hours, filter with absorbent cotton, pass the filtrate through a silica gel chromatography column, and finally elute and spin dry to obtain a cross-linking agent;

[0034] The structural formula of the crosslinking agent is: The molecular weight is 290.

[0035] Among them, the proportions of all raw materials for the synthesis of crosslinking agents in the total weight are: bis(2-hydroxyethyl) disulfide 5-8%, dichloromethane 67-70%, triethylamine 12-15%...

Embodiment 1

[0047] Step 1, add 5% of bis(2-hydroxyethyl) disulfide into a round bottom flask, add 70% dichloromethane, 12% triethylamine in turn under ice bath conditions, and slowly add 13% methacrylic acid Acyl chloride, the system is sealed and reacted for 3 hours at 0°C with magnetic stirring;

[0048] Transfer to a separatory funnel, add 17% NaHCO of the total weight of raw materials used for synthesis 3 (concentration 5%) solution washing, extracting 3 times with dichloromethane of 33% of the total weight of raw materials to remove unreacted bis(2-hydroxyethyl) disulfide; add anhydrous Na to the organic layer extract 2 SO 4 After drying for 8 hours, filter with absorbent cotton, pass the filtrate through a silica gel chromatography column, elute with petroleum ether and ethyl acetate (volume ratio 8:1) eluent, combine the eluent and spin dry to obtain a crosslinking agent;

[0049] Step 2: Add 0.5% polyethylene glycol monomethyl ether (n=1000) into a round bottom flask, add 29% te...

Embodiment 2

[0053] Step 1, add 8% bis(2-hydroxyethyl) disulfide into a round bottom flask, add 67% dichloromethane, 14% triethylamine in turn under ice bath conditions, and slowly add 11% methacrylic acid Acyl chloride, the system is sealed and reacted for 4 hours at 0°C with magnetic stirring;

[0054] Transfer to a separatory funnel, add 24% NaHCO of the total weight of raw materials used for synthesis 3 (concentration 5%) solution washing, extracting 3 times with dichloromethane of 35% of the total weight of raw materials to remove unreacted bis(2-hydroxyethyl) disulfide; add anhydrous Na to the organic layer extract 2 SO 4 After drying for 12 hours, filter with absorbent cotton, pass the filtrate through a silica gel chromatography column, elute with petroleum ether and ethyl acetate (volume ratio 10:1) eluent, and spin dry the combined eluent to obtain a crosslinking agent;

[0055] Step 2: Add 0.7% polyethylene glycol monomethyl ether (n=2000) into a round bottom flask, add 27% te...

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Abstract

The invention relates to a pH-redox double sensitive amphiphilic polymer of which the structural formula is disclosed in the specification, wherein X=15-35, Y=1-2, PEG is a polyethyleneglycol monomethyl ether chain segment, and the molecular weight is 9500-25000. The preparation method comprises the following steps: mixing raw materials, reacting in an oil bath in a nitrogen atmosphere, eluting, dissolving in dichloromethane, adding petroleum ether to precipitate under ice bath conditions, standing, centrifugating to remove solvent, dissolving in dichloromethane, flushing, carrying out centrifugal drying, and drying in an oven. By introducing the pH-sensitive monomer and redox-sensitive crosslinking agent into the polymer structure, the pH-redox double sensitive amphiphilic polymer has favorable pH sensitivity and redox sensitivity, can be used as a drug carrier material, has environment response capacity, can make a response according to the environmental change when arriving at the target spot position, and effectively implements controlled release of drugs.

Description

technical field [0001] The invention belongs to the technical field of polymers, and relates to a pH-redox double-sensitive amphiphilic polymer, and also relates to a preparation method of the pH-redox double-sensitive amphiphilic polymer. Background technique [0002] Environment-sensitive amphiphilic polymers are a class of polymers that can make structural changes in vivo or in vitro, and can self-assemble into micelles in aqueous solution. These micelles are mostly used in the in vivo delivery of fat-soluble drugs. When the external environment changes slightly, the micelles constructed by environment-responsive amphiphilic polymers will change their own properties such as disintegration or morphological transformation, and these changes can be used to control the drug release behavior. Many stimuli are available for constructing stimuli-responsive micelles, including internal stimuli such as pH value, redox environment, ionic strength, and biomolecules, and external st...

Claims

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Application Information

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IPC IPC(8): C08F283/06C08F220/34C08F222/24C08G65/48A61K47/34
Inventor 余丽丽尤静姚琳梁飞范涛杨黎燕王小库张韫
Owner XIAN MEDICAL UNIV
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