Folic acid modification of chitosan nucleophilic NO donator and compounding method thereof

A chitosan and modified technology, applied in the field of medical engineering, can solve problems such as low utilization rate, and achieve the effects of preventing restenosis, long release half-life, and promoting wound healing.

Inactive Publication Date: 2008-07-23
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the present invention, chitosan is modified by carboxylation to generate NH nucleophilic sites, and after reacting with NO, a series of [N(O)NO] containing [N(O)NO] - A new type of NO donor with functional groups, which solves the current problems (lower utilization) of this type of nucleophilic NO donor in clinical applications

Method used

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  • Folic acid modification of chitosan nucleophilic NO donator and compounding method thereof
  • Folic acid modification of chitosan nucleophilic NO donator and compounding method thereof
  • Folic acid modification of chitosan nucleophilic NO donator and compounding method thereof

Examples

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Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of folic acid (FA) modified 400,000 molecular weight chitosan (CS) / NO (molar ratio: FA / CS=2 / 1)

[0021] Accurately weigh 1.61g of chitosan (molecular weight: 400,000) sample, add 100ml of 1% acetic acid and stir until completely dissolved, adjust the pH value of the solution to 4.7, filter the solution with a disposable syringe filter and add it to a round bottom flask . Weigh 2.17g of folic acid and dissolve it in 30ml of dimethyl sulfoxide, stir it with magnetic force until it is completely dissolved, then add 0.5g of dicyclohexylcarbodiimide to the folic acid solution, and mix until it dissolves. The folic acid solution added with dicyclohexylcarbodiimide was added to the chitosan solution, and stirred and reacted in a water bath at 37° C. for 7 days. Adjust the pH value to 9.0 to terminate the reaction, dialyze the reaction product with a phosphate buffer solution with a pH value of 7.4 for 3 days, and then dialyze it with ultrapure wate...

Embodiment 2

[0024] Embodiment 2: the synthesis (molar ratio: FA / CS=1 / 1) of folic acid (FA) modified 1.24 million molecular weight chitosan (CS) / NO

[0025] Accurately weigh 1.61g of chitosan (molecular weight: 1.24 million) sample, add 100ml of 1% acetic acid and stir until completely dissolved, adjust the pH value of the solution to 4.7, filter the solution with a disposable syringe filter and add it to a round bottom flask . Weigh 4.34g of folic acid and dissolve it in 30ml of dimethyl sulfoxide, stir it with magnetic force until it is completely dissolved, then add 0.5g of dicyclohexylcarbodiimide to the folic acid solution, and mix until it dissolves. The folic acid solution added with dicyclohexylcarbodiimide was added to the chitosan solution, and stirred and reacted in a water bath at 37° C. for 7 days. Adjust the pH value to 9.0 to terminate the reaction, dialyze the reaction product with a phosphate buffer solution with a pH value of 7.4 for 3 days, and then dialyze it with ultr...

Embodiment 3

[0028] Embodiment 3: the synthetic (molar ratio: FA / CS=1 / 2) of folic acid (FA) modified 1.88 million molecular weight chitosan (CS) / NO

[0029] Accurately weigh 1.61g of chitosan (molecular weight 1.88 million) sample, add 100ml of acetic acid and stir until completely dissolved, adjust the pH value of the solution to 4.7, filter the solution with a disposable syringe filter and add it to a round bottom flask. Weigh 8.68g of folic acid and dissolve it in 30ml of dimethylsulfoxide, stir it with magnetic force until it is completely dissolved, then add 0.5g of dicyclohexylcarbodiimide to the folic acid solution, and mix until it dissolves. The folic acid solution added with dicyclohexylcarbodiimide was added to the chitosan solution, and stirred and reacted in a water bath at 37° C. for 7 days. Adjust the pH value to 9.0 to terminate the reaction, dialyze the reaction product with a phosphate buffer solution with a pH value of 7.4 for 3 days, and then dialyze it with ultrapure w...

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Abstract

The invention relates to a folic acid modified chitosan nucleophilic NO donor and a synthetic method for the folic acid modified chitosan NO donor and belongs to the field of medical engineering technology. The invention makes acylation modification to NH2 group on the chitosan to lead the NH2 to generate nucleophilic NH group which can react with NO; a secondary amine NH group on a folic acid modified chitosan molecule reacts with NO air molecules in methanol solution of sodium methylate to generate an (N(O)NO) <minus> group, and Na <plus>/NH is equal to 2 and a molecular structural formula of the obtained folic acid modified chitosan Nitric Oxide donor is provided. The nucleophilic NO donor of the invention provided with different NO release rates and longer half-life periods can overcome the weak points of non-specificity and targeting of the NO release, improve the utilization efficiency of NO and at the same time, the invention can overcome the cytotoxicity of nucleophilic agents (polyamines) and prevent the generation of carcinogenic by-product nitrosamine.

Description

technical field [0001] The invention relates to a medicine in the technical field of medical engineering and a synthesis method thereof, in particular to a folic acid modified chitosan nucleophilic NO donor and a synthesis method thereof. Background technique [0002] Nitric oxide (NO) is an endothelial-induced relaxation factor that plays an important role in regulating vascular tone, blood pressure, smooth muscle proliferation and platelet aggregation. Currently, controlled release of NO at the site of injury has been identified as one of the most promising approaches to prevent restenosis. An effective approach to treating patients with cardiovascular disease is the use of anticoagulant and antiplatelet agents that prevent further ischemic events and reduce the probability of death from thrombosis-related arterial disease. Contains nucleophilic nitric oxide donor [N(O)NO] - Compounds with functional groups are one of the most important NO donor drugs developed in recent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K47/36C08B37/08A61K47/61
Inventor 万锕俊孙燕李慧丽张隐西
Owner SHANGHAI JIAO TONG UNIV
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