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Hypoxia sensitive nitrobenzene chitosan and its preparation and application

A nitrophenylated 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 difficulty and rapidity of chitosan glycolipid grafts drug release and other issues to achieve the effect of improving drug efficacy and improving release efficiency

Active Publication Date: 2021-06-04
ZHEJIANG UNIV
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  • 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

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  • Hypoxia sensitive nitrobenzene chitosan and its preparation and application
  • Hypoxia sensitive nitrobenzene chitosan and its preparation and application
  • Hypoxia sensitive nitrobenzene chitosan and its preparation and application

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...

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Abstract

The invention provides a hypoxia-sensitive nitrobenzene chitosan and its preparation and application. The chitosan has a weight-average molecular weight of 5000-18000 Da and a nitrobenzene grafting rate of 5.3-14.8%. The invention adopts chitosan with good biocompatibility as the hydrophilic material, uses 6-aminocaproic acid as the bridging group, selects nitrobenzene as the anoxic sensitive group, and synthesizes nitrobenzene with anoxic sensitive response. phenylated chitosan. The nitrobenzene chitosan can self-assemble into polymer micelles in water. The nitrobenzene chitosan can be used as an excellent drug carrier with good biological safety, and can efficiently encapsulate a variety of cytotoxic drugs. Under the action of the nitroreductase in the drug, it depolymerizes and releases the drug quickly, realizes the targeted and rapid release of the drug, and improves the efficacy of the drug. The structural formula of nitrobenzene chitosan of the present invention is:

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

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Application Information

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Patent Type & Authority Patents(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
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