Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Double-sensitive amphiphilic copolymer containing Schiff base and mercapto group on same side group, as well as preparation method and application of double-sensitive amphiphilic copolymer

An amphiphilic copolymer and dual-sensitivity technology, which can be used in medical preparations, drug combinations, and pharmaceutical formulations with non-active ingredients. , good acid sensitivity and redox sensitivity, the effect of promoting rapid release

Inactive Publication Date: 2015-01-07
TIANJIN UNIV
View PDF3 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above studies did not solve the problem of the stability of nanoparticles and the rapid release of drugs from tumor sites.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Double-sensitive amphiphilic copolymer containing Schiff base and mercapto group on same side group, as well as preparation method and application of double-sensitive amphiphilic copolymer
  • Double-sensitive amphiphilic copolymer containing Schiff base and mercapto group on same side group, as well as preparation method and application of double-sensitive amphiphilic copolymer
  • Double-sensitive amphiphilic copolymer containing Schiff base and mercapto group on same side group, as well as preparation method and application of double-sensitive amphiphilic copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: In the reactor, add the amphiphilic diblock copolymer polyethylene glycol monomethyl ether-b-polycaprolactone (mPEG-b-(PCL-g -PMAA)), wherein the mass ratio of polyethylene glycol segment / polyester segment is 1:2, and the mol ratio of carboxyl and polyester segment structural unit is 1:4, adds p-Hydroxybenzaldehyde 0.055g (0.5mmol), DCC 0.2g (1mmol), DMAP 0.12g (0.1mmol), add 10mL of dichloromethane, react at room temperature, after the reaction, precipitate in a large amount of glacial ether, and dry in vacuum to obtain the amphiphilic copolymer mPEG- b-(PCL-g-P(MAA-Hy)); Add 0.1g of mPEG-b-(PCL-g-P(MAA-Hy)) into the reactor, add mercaptoethylamine 0.12g (1mmol), and react at room temperature , precipitated in glacial ether, filtered, and vacuum-dried to obtain a dual-sensitive amphiphilic copolymer PECMHC containing Schiff base and mercapto groups on the same side group.

Embodiment 2

[0023] Add 0.1 g of amphiphilic diblock copolymer polyethylene glycol monomethyl ether-b-polycaprolactone (mPEG-b-(PCL-g-PMAA)) containing side carboxyl groups in the polyester segment to the reactor , wherein the mass ratio of polyethylene glycol segment / polyester segment is 1:1, the mol ratio of carboxyl group and polyester segment structural unit is 1:2, adds p-hydroxybenzaldehyde 0.05g (0.4mmol), DCC 0.5g ( 0.5mmol), DMAP 0.24g (0.22mmol), add 10mL of dichloromethane, react at room temperature, precipitate in a large amount of glacial ether after the reaction, and dry in vacuum to obtain the amphiphilic copolymer mPEG-b-( PCL-g-P(MAA-Hy)); 0.1g of mPEG-b-(PCL-g-P(MAA-Hy)) was added to the reactor, mercaptoethylamine 0.05g (0.44mmol) was added, and after reaction at room temperature, Precipitate in glacial ether, filter, and vacuum-dry to obtain a dual-sensitive amphiphilic copolymer PECMHC containing Schiff base and mercapto groups on the same side group.

Embodiment 3

[0025] Add 0.1 g of amphiphilic diblock copolymer polyethylene glycol monomethyl ether-b-polycaprolactone (mPEG-b-(PCL-g-PMAA)) containing side carboxyl groups in the polyester segment to the reactor , wherein the mass ratio of polyethylene glycol section / polyester section is 1:4, the mol ratio of carboxyl group and polyester section structural unit is 1:2, adds p-hydroxybenzaldehyde 1.6g (1.7mmol), DCC 0.33g ( 1.7mmol), DMAP 0.012g (0.17mmol), add dichloromethane 10mL, react at room temperature, precipitate in a large amount of glacial ether after the completion of the reaction, and vacuum dry to obtain the amphiphilic copolymer mPEG-b-( PCL-g-P(MAA-Hy)); 0.1g of mPEG-b-(PCL-g-P(MAA-Hy)) was added to the reactor, mercaptoethylamine 0.8g (0.66mmol) was added, and after reaction at room temperature, Precipitate in glacial ether, filter, and vacuum-dry to obtain a dual-sensitive amphiphilic copolymer PECMHC containing Schiff base and mercapto groups on the same side group.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a double-sensitive amphiphilic copolymer containing a Schiff base and a mercapto group on a same side group, as well as a preparation method and application of the double-sensitive amphiphilic copolymer. The copolymer is the amphiphilic copolymer which introduces an acid-sensitive bond, namely the Schiff base and a redox-sensitive group, namely the mercapto group on the same side group on the basis of a polyethylene glycol / polyester amphiphilic copolymer containing a side carboxyl group in a polyester segment. The copolymer can form acid-sensitive and redox-sensitive reversible cross-linked nanoparticles with physical entrapment of a medicament by self-assembly, namely that a disulfide bond is formed by oxidation of the mercapto group for cross-linking, and the fracture of the mercapto group or the Schiff base is produced by reduction of the disulfide bond, thereby disintegrating a cross-linked structure. The fracture of any bond of the Schiff base and the disulfide bond can promote the disintegration of the double-sensitive polymer nanoparticles and the release of the medicament and further improve the bioavailability of the medicament in an acidic micro-environment of tumor cells and high concentration of glutathione (GSH).

Description

technical field [0001] The invention relates to a dual-sensitive amphiphilic copolymer containing Schiff base and mercapto group on the same side group and its preparation method and application, in particular to a dual-sensitive amphiphilic copolymer containing acid-sensitive Schiff base and redox sensitive copolymer on the same side group. The dual-sensitive amphiphilic copolymer of mercapto groups belongs to [1] the amphiphilic copolymer nanoparticle technology. technical background [0002] Amphiphilic copolymer self-assembled nanoparticles have been extensively studied as ideal carriers for the delivery of hydrophobic anticancer drugs. Polymeric nanoparticles have many advantages, such as improving the solubility of drugs, selectively permeating tumor sites through the EPR effect, and so on. Nanoparticles are in a thermally stable state, and there is an equilibrium between aggregation and disaggregation affected by the critical micelle concentration (CMC). When the na...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/91C08G81/00A61K47/34A61K9/14A61P35/00
Inventor 邓联东董岸杰邓宏章
Owner TIANJIN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com