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Hypoxia sensitive response type chitosan-nitroimidazole graft, and preparation method and application thereof

A technology of nitroimidazole and chitosan, which is applied in the application field of chitosan nitroimidazole grafts as hypoxia-sensitive responsive drug release carriers, can solve problems such as difficult to achieve rapid and effective drug release, and achieve improved Effects of drug release efficiency, improvement of drug efficacy, and stable properties

Inactive Publication Date: 2019-11-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult to achieve rapid and effective drug release in hypoxic lesions with the existing chitosan fatty acid grafts to construct a drug delivery system.

Method used

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  • Hypoxia sensitive response type chitosan-nitroimidazole graft, and preparation method and application thereof
  • Hypoxia sensitive response type chitosan-nitroimidazole graft, and preparation method and application thereof
  • Hypoxia sensitive response type chitosan-nitroimidazole graft, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029]Accurately weigh 64.8mg 2-nitroimidazole, 39.6mg potassium carbonate and 128.5mg N-Boc-6-bromohexylamine into a 50mL dry round bottom flask, add 10mL dehydrated N,N-dimethylformamide ( N, N-dimethylformamide, DMF), reacted at 80°C for 4h in a constant temperature heating magnetic stirrer. After the reaction, centrifuge to take the supernatant of the reaction solution, add 100mL deionized water and 20mL ethyl acetate, shake at room temperature on an air bath oscillator for 5min, and let it stand for 30min. After the liquid is separated, take the upper layer of ethyl acetate and place it in a Round-bottomed flask, evaporating in a water bath at 40°C on a rotary evaporator until the solution in the flask is completely removed. Add 30mL of DMF, 73.4mg of disuccinimidyl carbonate (N,N'-Disuccinimidyl Carbonate, DSC), 186.8mg of chitosan (Mw=2000Da) and 30mL of deionized water into the flask, and heat it in a magnetic stirrer at a constant temperature of 40°C After 24 hours o...

Embodiment 2

[0031] Accurately weigh 64.8mg of 2-nitroimidazole, 79.2mg of potassium carbonate and 160.6mg of N-Boc-6-bromohexylamine into a 50mL dry round bottom flask, add 20mL of dehydrated DMF, and heat in a magnetic stirrer at a constant temperature for 80 ℃ reaction 4h. After the reaction, centrifuge to take the supernatant of the reaction solution, add 100mL deionized water and 20mL ethyl acetate, shake at room temperature on an air bath oscillator for 5min, and let it stand for 30min. After the liquid is separated, take the upper layer of ethyl acetate and place it in a Round-bottomed flask, evaporating in a water bath at 40°C on a rotary evaporator until the solution in the flask is completely removed. Add 30mL DMF, 146.8mg DSC, 373.6mg chitosan (Mw=5000Da) and 30mL deionized water into the flask, and react in a constant temperature heating magnetic stirrer at 40°C for 24h to obtain a reaction product. The reaction product was placed in a dialysis bag (MWCO 3500Da) and dialyzed f...

Embodiment 3

[0033] Accurately weigh 64.8mg 2-nitroimidazole, 158.2mg potassium carbonate and 240.9mg N-Boc-6-bromohexylamine into a 50mL dry round bottom flask, add 20mL dehydrated DMF, and heat in a magnetic stirrer at a constant temperature for 80 ℃ reaction 4h. After the reaction, centrifuge to take the supernatant of the reaction solution, add 100mL deionized water and 20mL ethyl acetate, shake at room temperature on an air bath oscillator for 5min, and let it stand for 30min. After the liquid is separated, take the upper layer of ethyl acetate and place it in a Round-bottomed flask, evaporating in a water bath at 40°C on a rotary evaporator until the solution in the flask is completely removed. Add 30mL DMF, 220.2mg DSC, 934.1mg chitosan (Mw=20000Da) and 30mL deionized water into the flask, and react in a constant temperature heating magnetic stirrer at 40°C for 24h to obtain a reaction product. The reaction product was placed in a dialysis bag (MWCO 3500Da) and dialyzed for 48 hour...

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Abstract

The invention provides a hypoxia sensitive response type chitosan-nitroimidazole graft, and a preparation method and an application thereof. The weight average molecular weight of chitosan is 2000-20000 Da, and the grafting ratio of nitroimidazole is 1-20%. The hypoxia sensitive response type chitosan-nitroimidazole graft is synthesized by adopting chitosan with a good biocompatibility as a hydrophilic material, N-Boc-bromoalkylamine as a bridging group and nitroimidazole as an anoxic sensitive group. The graft material self-aggregates in water to form polymer micelles, and has a low criticalmicelle concentration; and the chitosan-nitroimidazole graft can be used as a drug carrier, and drug-loaded nanoparticles formed by combining the graft with a drug can rapidly release the drug under the action of nitroreductase highly expressed in hypoxia cells, realizes the targeted release of the drug in the environment of hypoxic lesions such as tumors and stroke, and improves the drug effects.The structural formula of the chitosan-nitroimidazole graft of the present invention is shown in the description.

Description

technical field [0001] The invention belongs to compound synthesis, and relates to a synthesis method of a hypoxia sensitive and responsive chitosan nitroimidazole graft and an application of the chitosan nitroimidazole graft as a hypoxia sensitive and responsive drug release carrier. Background technique [0002] Nano-drugs can achieve targeted distribution of lesions, and targeted drug delivery can improve drug effectiveness and reduce toxic and side effects. However, there are still problems in the release of nano-drugs to target sites. According to the pathological properties of diseases, designing environment-responsive drug carriers is an effective means to achieve targeted drug release. [0003] Under the condition of hypoxia, the body will undergo a series of physiological and pathological changes. Oxygen is an essential substance for cells to carry out normal physiological activities. During hypoxia, the glycolysis process gradually replaces aerobic respiration a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/36
CPCA61K47/36C08B37/003
Inventor 胡富强刘璇商旭炜周雪晴袁弘孟廷廷
Owner ZHEJIANG UNIV
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