PH response type curcumin and succinic anhydride prodrug nanometer micelle and preparation method and application thereof

A technology of curcumin succinic anhydride and nano micelles, which can be applied in nanotechnology, nanotechnology, nanotechnology and other directions for materials and surface science, and can solve the problems of poor absorption, low bioavailability, and poor water solubility of curcumin.

Pending Publication Date: 2020-03-27
SOUTH CHINA UNIV OF TECH
View PDF6 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many studies have shown that curcumin has extremely poor water solubility, poor absorption in the body, and low bioavailability, which is why it cannot become a mainstream therapeutic drug
Therefore, curcumin has poor water solubility and low bioavailability is another key problem to be solved.
[0007] And L.Lv, Y.Guo, Y.Shen, J.Liu, W.Zhang, D.Zhou, S.Guo, IntracellularlyDegradable, Self-Assemb

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
  • PH response type curcumin and succinic anhydride prodrug nanometer micelle and preparation method and application thereof
  • PH response type curcumin and succinic anhydride prodrug nanometer micelle and preparation method and application thereof
  • PH response type curcumin and succinic anhydride prodrug nanometer micelle and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] mPEG 350 -Synthesis of SA-Cur

[0079] (1) mPEG modified SA with a molecular weight of 350: Weigh 8g of mPEG respectively 350 (Polyethylene glycol monomethyl ether), 2.5 g of succinic anhydride, and 0.68 g of p-toluene sulfonic acid are placed in a flask under nitrogen environment protection and reacted at 80° C. for 3 hours. The product after the reaction was dissolved in 20ml of dichloromethane, filtered to take the filtrate, and then repeatedly recrystallized with 120ml of anhydrous ether at -15°C and freeze-dried to obtain the SA-modified mPEG product (mPEG 350 -SA);

[0080] (2)mPEG 350 -SA modified curcumin: weigh the mPEG product (mPEG) modified with SA described in step (1) 350 -SA) 1.8g, curcumin drugs (0.5g), N,N'-dicyclohexylcarbodiimide (1.2g), 4-dimethylaminopyridine (0.1g), triethylamine (0.1mL) added Ultra-dry dichloromethane solution (50ml), mix well, react for 12h under a nitrogen atmosphere, filter the reacted solution to remove the precipitate, then mix th...

Embodiment 2

[0083] mPEG 550 -Synthesis of SA-Cur

[0084] (1) mPEG modified SA with a molecular weight of 550: Weigh 8g of mPEG respectively 550 (Polyethylene glycol monomethyl ether), 1.6 g of succinic anhydride, and 0.56 g of p-toluene sulfonic acid are placed in a flask under nitrogen environment protection and reacted at 80° C. for 3 hours. The product after the reaction was dissolved in 30ml of dichloromethane, filtered to take the filtrate, and then repeatedly recrystallized with 160ml of anhydrous ether at -5°C and freeze-dried to obtain the SA-modified mPEG product (mPEG 550 -SA);

[0085] (2)mPEG 550 -SA modified curcumin: weigh the mPEG product (mPEG) modified with SA described in step (1) 550 -SA) 2.7g, curcumin drugs (0.54g), N,N'-dicyclohexylcarbodiimide (1.4g), 4-dimethylaminopyridine (0.1g), triethylamine (0.1mL) React in an ultra-dry dichloromethane solution (50ml) under a nitrogen atmosphere for 12h, filter the reacted solution to remove the precipitate, then mix the filtrate ...

Embodiment 3

[0088] mPEG 750 -Synthesis of SA-Cur

[0089] (1) mPEG modified SA with a molecular weight of 750: weigh 8g of mPEG respectively 750 (Polyethylene glycol monomethyl ether), 1.32g of succinic anhydride, 0.42g of p-toluenesulfonic acid in a flask, under nitrogen environment protection, react at 80°C for 3h. The reacted product was dissolved in 30ml of dichloromethane, filtered to take the filtrate, and then repeatedly recrystallized with 200ml of anhydrous ether at 0°C and freeze-dried to obtain the SA-modified mPEG product (mPEG 750 -SA);

[0090] (2)mPEG 750 -SA modified curcumin: weigh the mPEG product (mPEG) modified with SA described in step (1) 750 -SA) 2.5g, curcumin drugs (0.38g), N,N'-dicyclohexylcarbodiimide (0.9g), 4-dimethylaminopyridine (0.1g), triethylamine (0.1mL) In ultra-dry dichloromethane solution (50ml), mix well, react for 12h under a nitrogen atmosphere, filter the reacted solution to remove the precipitate, then mix the filtrate with 300mL of anhydrous ether an...

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
The average particle sizeaaaaaaaaaa
Particle sizeaaaaaaaaaa
Login to view more

Abstract

The invention discloses a pH response type curcumin and succinic anhydride prodrug nanometer micelle and a preparation method and application thereof. The nanometer micelle consists of the following components in percentage by mass of 63.5%-91.9% of carrier auxiliary materials and 8.13%-39.5% of curcumin medicines. A nanometer micelle monomer is an amphiphilic block, and consists of a hydrophilicblock and a lyophobic block, wherein the hydrophilic block is succinic anhydride modified methoxyl polyethylene glycol, the lyophobic block is curcumin molecules, and the weight ratio of the hydrophilic block to the lyophobic block is (1 to 1) to (12 to 1). The pH response type curcumin and succinic anhydride prodrug nanometer micelle disclosed by the invention has the advantages that succinic anhydride sensitive to acid is designed and introduced at the end of the polyethylene glycol and is bonded with a lyophobic medicine namely the curcumin, and the formed amphiphilic polymer is self-assembled in an aqueous solution to form the nanometer micelle, so that the water solubility and the stability of an original medicine are increased; and the nanometer micelle monomer can degrade to releaseout cancer resisting medicines namely curcumin body medicines under the action of acid in cancer cells, so that pinpoint controlled release effects can be achieved.

Description

Technical field [0001] The invention belongs to the field of novel nanomedicine, and particularly relates to a pH-responsive curcumin succinic anhydride prodrug nanomicelle, and a preparation method and application thereof. Background technique [0002] Curcumin is a polyphenolic extract in the traditional Chinese medicine turmeric, which is listed as the third-generation cancer chemopreventive by the US FDA. Studies have shown that curcumin has a strong preventive effect on the three stages of tumor carcinogenesis. It is a natural tumor chemopreventive and therapeutic agent with multi-target characteristics. Curcumin achieves anti-tumor effects by regulating genes related to cancer cell proliferation, apoptosis, infiltration and angiogenesis. But curcumin is extremely difficult to dissolve in water, poor oral absorption, low bioavailability and other shortcomings, which have become the key bottleneck for its clinical application. [0003] Nanomicelles are a new type of drug carr...

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
IPC IPC(8): A61K47/69A61K31/12A61K47/60A61P35/00B82Y5/00B82Y30/00B82Y40/00
CPCA61K31/12A61K47/6907A61K47/60A61P35/00B82Y5/00B82Y30/00B82Y40/00
Inventor 王迎军杜昶徐东
Owner SOUTH CHINA UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap