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

A kind of ph and redox double response amphiphilic block copolymer and its preparation method and application

An amphiphilic copolymer and dual-response technology, which can be used in pharmaceutical formulations, medical preparations with inactive ingredients, and emulsion delivery.

Active Publication Date: 2019-05-07
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the conventional copolymers poly(ethylene imine) (PEI) used in basic research are mostly refractory materials, which are more harmful to organisms, while Poly(β-amino esters) (PAE) has good biocompatibility , can be degraded, and can be protonated from insoluble to soluble in an acidic environment, with excellent performance
[0007] However, so far, few literatures and patents have reported that PAE-based pH and Redox dual-responsive amphiphilic block copolymers can simultaneously achieve long-term circulation of drug-loaded micelles in blood, accumulation in cancer tissues, and Increased cancer cell uptake and efficient drug release due to disruption of micellar structure in response to the internal environment of cancer cells

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
  • A kind of ph and redox double response amphiphilic block copolymer and its preparation method and application
  • A kind of ph and redox double response amphiphilic block copolymer and its preparation method and application
  • A kind of ph and redox double response amphiphilic block copolymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Example 1: Preparation of pH and Redox double responsive amphiphilic copolymer MPEG-Linker-PAE-ss-PLGA

[0103] (1) Preparation of pH-responsive hydrophilic macromer MPEG-Linker: under inert gas protection and anhydrous conditions, solvent DCM (20mL), catalyst DCC (41mg, 0.2mmol), DMAP (4.88mg, 0.04mmol), monomer MPEG (80mg, 0.02mmol), and small molecule monomer FA (45mg, 0.3mmol) were added to a 100mL round bottom flask, and under stirring conditions, at room temperature, after 24 hours of reaction, the reaction solution was filtered. Remove the precipitate therein, collect the filtrate and concentrate it by rotary evaporation and slowly add it to 10 times (volume ratio) of cold isopropanol, place it in the refrigerator for 2h, collect the precipitate, wash the precipitate with isopropanol and diethyl ether, and obtain a solid. ℃, 35mbar and vacuum drying for 48h to obtain the aldehyde-terminated macromonomer MPEG-CHO, and the DMSO solution (20mL) of MPEG-CHO (41.32mg,...

Embodiment 2

[0109] Example 2: Preparation of pH and Redox double responsive amphiphilic copolymer MPEG-Linker-PAE-ss-PLGA

[0110] (1) Preparation of pH-responsive hydrophilic macromer MPEG-Linker: under inert gas protection and anhydrous conditions, solvent DCM (30mL), catalyst DCC (51.25mg, 0.25mmol), DMAP (30.5mg , 0.25mmol), monomer MPEG (40mg, 0.01mmol), and small molecule monomer FA (75mg, 0.5mmol) were added to a 100mL round-bottomed flask, and the reaction solution was filtered under stirring at room temperature for 24 hours. , remove the precipitate therein, collect the filtrate and slowly add it to 10 times (volume ratio) of cold isopropanol after being concentrated by rotary evaporation, place it in the refrigerator for 2h, collect the precipitate, wash the precipitate with isopropanol and diethyl ether, and obtain a solid. Vacuum-dried at 35°C and 35mbar for 48h to obtain the aldehyde-terminated macromer MPEG-CHO. MPEG-CHO (41.32mg, 0.01mmol) and DAP (1.67mL, 0.02mmol) in DMSO...

Embodiment 3

[0113] Example 3: Preparation of pH and Redox double responsive amphiphilic copolymer MPEG-Linker-PAE-ss-PLGA

[0114](1) Preparation of pH-responsive hydrophilic macromer MPEG-Linker: under inert gas protection and anhydrous conditions, solvent DCM (20mL), catalyst DCC (4.1mg, 0.02mmol), DMAP (2.44mg , 0.02mmol), monomer MPEG (80mg, 0.02mmol), small molecule monomer FA (9mg, 0.06mmol) were added to a 100mL round bottom flask, and under stirring conditions, room temperature, after 24h reaction, the reaction solution was filtered , remove the precipitate therein, collect the filtrate and slowly add it to 10 times (volume ratio) of cold isopropanol after being concentrated by rotary evaporation, place it in the refrigerator for 2h, collect the precipitate, wash the precipitate with isopropanol and diethyl ether, and obtain a solid. Vacuum drying at 35°C and 35mbar for 48h to obtain the aldehyde-terminated macromonomer MPEG-CHO, MPEG-CHO (41.32mg, 0.01mmol) and DAP (4.17mL, 0.05m...

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

PropertyMeasurementUnit
critical micelle concentration (mass)aaaaaaaaaa
particle diameteraaaaaaaaaa
particle diameteraaaaaaaaaa
Login to View More

Abstract

The invention provides a pH and Redox dual-response amphiphilic block copolymer as well as a preparation method and application thereof. The molecular formula of the copolymer provided by the invention is MPEG-Linker-PAE-ss-PLGA and the copolymer has a structure as shown in the formula I and can be prepared through the following steps of performing reaction to modify macromonomer methoxypolyethylene glycols (MPEG), thereby obtaining hydrophilic macromonomer (MPEG-Linker) with pH responsiveness; performing reaction to modify macromonomer polylactic acid-poly lactic-co-glycolic acid (PLGA) by use of disulfide bonds, thereby obtaining a hydrophobic macromonomer (PLGA-Cys) with Redox responsiveness; and performing michael addition reaction through a one-step method so as to obtain the copolymer. The copolymer provided by the invention can be used in systems for loading water-insoluble drug micelle, is capable of controlling slow release of loaded drugs in normal tissues, is low in release amount accumulated for a long time, and can be enriched and rapidly released in focus tissues, thereby improving the bioavailability and treatment effect of the medicaments.

Description

technical field [0001] The invention belongs to the technical field of polymer copolymer materials for biomedicine, and in particular relates to a pH- and Redox dual-response amphiphilic block copolymer and its preparation method and application. Background technique [0002] Nowadays, cancer has become the first cause of death of human diseases, and the morbidity and mortality are still rising, posing a huge threat to human health. According to statistics, more than 2.8 million people died of cancer in China in 2015, an average of 7,500 people per day. Cancer has increasingly become the main killer of human life and health. [0003] The treatment of cancer includes chemotherapy, radiotherapy and surgery, among which chemotherapy is the most important and effective treatment in clinical practice. The hydrophobic small molecule chemotherapeutic drugs used clinically, such as doxorubicin, camptothecin, paclitaxel, etc., have poor water solubility, cannot carry out stable long...

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 Patents(China)
IPC IPC(8): A61K9/107A61K47/34C08G81/00C08G73/00
CPCA61K9/107A61K47/10A61K47/34C08G73/00C08G81/00
Inventor 陈春英张灿阳徐梦真吴军光
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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