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

Hypoxia-sensitive nitrobenzenized chitosan and preparation method and application thereof

A nitrobenzene-chitosan, sensitive technology, applied in the direction of organic active ingredients, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problem of chitosan glycolipid grafts quickly Drug release and other issues to achieve the effect of improving drug efficacy and release efficiency

Active Publication Date: 2020-06-19
ZHEJIANG UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the chitosan glycolipid graft is difficult to respond to the special microenvironment of the tumor to achieve rapid drug release

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
  • Hypoxia-sensitive nitrobenzenized chitosan and preparation method and application thereof
  • Hypoxia-sensitive nitrobenzenized chitosan and preparation method and application thereof
  • Hypoxia-sensitive nitrobenzenized chitosan and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1. Synthesis of Nitrophenylated Chitosan

[0027] Accurately weigh 210.1mg benzyl p-nitrochloroformate, 106.2mg 6-aminocaproic acid and 542μL triethylamine, suspend in 15mL dichloromethane, place in a 50mL dry round bottom flask, nitrogen atmosphere, ice-water bath for 10min, room temperature Reaction 12h. After the reaction, extract with 75mL deionized water and 15mL ethyl acetate, shake at room temperature with a vortex shaker, and let it stand still. After layering, take the upper layer of ethyl acetate, put it in a dry round bottom flask, and remove the solvent by rotary evaporation at 40°C. Add 15mL of N,N-dimethylformamide, 747.2mg of carbodiimide, 1034.7mg of chitosan (Mw=5000Da) and 15mL of deionized water into the flask, and heat at a constant temperature in a magnetic stirrer at 50°C for 16h to obtain the reaction product. The reactant was dialyzed in a dialysis bag (MWCO 3500Da) for 3 days to remove N,N-dimethylformamide and water-soluble by-products. Afte...

Embodiment 2

[0035] 1. Synthesis of Nitrophenylated Chitosan

[0036] Accurately weigh 224.1mg of benzyl p-nitrochloroformate, 272.7mg of 6-aminocaproic acid and 437μL of triethylamine, suspend in 10mL of dichloromethane, place in a 50mL dry round bottom flask, nitrogen atmosphere, ice-water bath for 10min, room temperature Reaction 24h. After the reaction, add 50 mL of deionized water and 10 mL of ethyl acetate for extraction, shake at room temperature with a vortex oscillator, and let stand. After layering, take the upper layer of ethyl acetate, put it in a dry round bottom flask, and remove the solvent by rotary evaporation at 40 °C. Add 10mL of N,N-dimethylformamide, 1196.3mg of carbodiimide, 1164.2mg of chitosan (Mw=5000Da) and 10mL of deionized water into the flask, and heat the reaction in a magnetic stirrer at 60°C for 12h to obtain the reaction product. The reactant was dialyzed in a dialysis bag (MWCO 3500Da) for 2 days to remove N,N-dimethylformamide and water-soluble by-produ...

Embodiment 3

[0042] 1. Synthesis of Nitrophenylated Chitosan

[0043] Accurately weigh 258.6mg of benzyl p-nitrochloroformate, 314.7mg of 6-aminocaproic acid and 504μL of triethylamine, suspend in 10mL of dichloromethane, place in a 50mL dry round bottom flask, nitrogen atmosphere, ice-water bath for 10min, room temperature Reaction 24h. After the reaction, add 50 mL of deionized water and 10 mL of ethyl acetate for extraction, shake at room temperature with a vortex oscillator, and let stand. After layering, take the upper layer of ethyl acetate, put it in a dry round bottom flask, and remove the solvent by rotary evaporation at 40 °C. Add 10mL of N,N-dimethylformamide, 1380.2mg of carbodiimide, 447.8mg of chitosan (Mw=5000Da) and 10mL of deionized water into the flask, and heat at a constant temperature in a magnetic stirrer at 60°C for 12h to obtain the reaction product. The reactant was dialyzed in a dialysis bag (MWCO 3500Da) for 2 days to remove N,N-dimethylformamide and water-solu...

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
particle diameteraaaaaaaaaa
particle diameteraaaaaaaaaa
particle diameteraaaaaaaaaa
Login to View More

Abstract

The invention provides hypoxia-sensitive nitrobenzenized chitosan and a preparation method and application thereof. The weight-average molecular weight of the chitosan is 5000-18000Da, and a graftingrate of nitrobenzene is 5.3-14.8%. Chitosan with good biocompatibility is used as a hydrophilic material, 6-aminocaproic acid is used as a bridging group, nitrobenzene is selected as an oxygen deficitsensitive group, and nitrobenzene chitosan with oxygen deficit sensitive responsiveness is synthesized. The nitrobenzene chitosan can be self-assembled into polymer micelles in water, can be used asan excellent drug carrier with good biological safety, efficiently encapsulates a variety of cytotoxic drugs, and rapidly depolymerizes and releases the drugs under the action of nitroreductase in anoxic tumor cells, so as to realize targeted rapid release of the drugs and improve the drug effect. The nitrobenzene chitosan disclosed by the invention has a structural formula shown in the specification,

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to anoxic sensitive nitrobenzoic chitosan and its synthesis method, and the application of nitrobenzoic chitosan as a hypoxia sensitive and responsive carrier in the preparation of various antitumor drugs. Background technique [0002] Tumors seriously threaten human health. Due to the lack of specific distribution in vivo, anticancer drugs have limited anticancer efficacy and are prone to toxic and side effects. Polymer micelles can effectively improve the distribution of drugs in vivo by virtue of their nanometer properties, especially micelles modified with specific targets can achieve specific distribution of tumor lesions, improve drug efficacy, and reduce toxic and side effects. However, while achieving specific distribution of polymer micelles, it is still difficult to solve the problem of rapid drug release at the target site. In order to further improve the anti-tumor efficacy, it i...

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): C08B37/08A61K9/107A61K47/36A61K31/704A61K31/136A61P35/00
CPCA61K9/1075A61K31/136A61K31/704A61K47/36A61P35/00C08B37/003
Inventor 胡富强商旭炜刘璇余芳英孟廷廷袁弘
Owner ZHEJIANG 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