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Synthesis of quaternary ammonium salt modified nucleophilic NO donor

A synthesis method and chitosan technology, applied in the field of medical engineering, can solve the problems of non-homogeneous reaction, nucleophilic NO donors cannot be directly targeted, etc., to achieve stable chemical properties, improve antithrombotic performance, and prevent restenosis Effect

Inactive Publication Date: 2007-11-07
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the problem that such nucleophilic NO donors cannot be directly targeted and react homogeneously

Method used

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  • Synthesis of quaternary ammonium salt modified nucleophilic NO donor
  • Synthesis of quaternary ammonium salt modified nucleophilic NO donor
  • Synthesis of quaternary ammonium salt modified nucleophilic NO donor

Examples

Experimental program
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Embodiment 1

[0033] This embodiment 1 is implemented under the following conditions of implementation and technical requirements:

[0034](1) Synthesis of N-monoquaternary ammonium chitosan (HTCC): Chitosan (6g, 37.0mmol) was dissolved in deionized water (60ml), and GTMAC (7.1ml, 111mmol) was dissolved at a reaction temperature of 85°C. It was added to the above reaction solution three times at intervals of two hours. After reacting for 10 hours, the transparent yellow reaction solution was added to ice acetone (200ml) solution, stirred and placed in the refrigerator overnight. The next day, the acetone was discarded and ethanol was added to dissolve, and then precipitated with a 4:1 acetone-ethanol solution, washed by pumping rate, and the final product was dried in a vacuum oven at 60°C to obtain 10.23 g of a light yellow powder.

[0035] (2) Synthesis of quaternary ammonium salt modified chitosan / NO donor: 1.2g (0.004mol) of quaternary ammonium salt modified chitosan was added to 100ml...

Embodiment 2

[0038] This embodiment 2 is implemented under the following conditions of implementation and technical requirements:

[0039] (1) Synthesis of N-monoquaternary ammonium chitosan (HTCC): Chitosan (6g, 37.0mmol) was dissolved in deionized water (60ml), and GTMAC (7.1ml, 111mmol) was dissolved at a reaction temperature of 85°C. It was added to the above reaction solution three times at intervals of two hours. After reacting for 17 hours, the transparent yellow reaction solution was added to a solution of ice acetone (200 ml), stirred and placed in the refrigerator overnight. The next day, the acetone was discarded and ethanol was added to dissolve, and then precipitated with a 4:1 acetone-ethanol solution, washed with pumping rate, and the final product was dried in a vacuum oven at 60°C to obtain 10.72 g of a light yellow powder.

[0040] (2) Synthesis of quaternary ammonium salt modified chitosan / NO donor: 1.2g (0.004mol) of quaternary ammonium salt modified chitosan was added...

Embodiment 3

[0043] This embodiment 3 is implemented under the following conditions of implementation and technical requirements:

[0044] (1) Synthesis of N-monoquaternary ammonium chitosan (HTCC): Chitosan (6g, 37.0mmol) was dissolved in deionized water (60ml), and GTMAC (7.1ml, 111mmol) was dissolved at a reaction temperature of 85°C. It was added to the above reaction solution three times at intervals of two hours. After 24 hours of reaction, the transparent yellow reaction solution was added to a solution of ice acetone (200 ml), stirred and placed in the refrigerator overnight. The next day, the acetone was discarded and ethanol was added to dissolve, and then precipitated with a 4:1 acetone-ethanol solution, washed by pumping rate, and the final product was dried in a vacuum oven at 60°C to obtain 11.02 g of yellow powder.

[0045] (2) Synthesis of quaternary ammonium salt modified chitosan / NO donor: 1.2g (0.004mol) of quaternary ammonium salt modified chitosan was added to 100ml o...

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Abstract

The present invention is synthesis of quaternary ammonium salt modified nucleophilic chitosan NO donor, and belongs to the field of medicine engineering technology. The synthesis includes the following steps: 1. reacting chitosan to quaternary aminate its NH2 radical and obtain ammonium salt modified chitosan molecule; and 2. reacting the ammonium salt modified chitosan molecule with NO gas molecule at high pressure in methanol solution of sodium methoxide to produce [N(O)NO] radical; washing the product with methanol and ether for several times, separating to purify, re-crystallizing, vacuum drying at room temperature and storing in a drier at -20 deg.c. The quaternary ammonium salt modified nucleophilic chitosan NO donor of the present invention has stable chemical property and relatively long release half life, and may be applied widely in treating cardiac vascular diseases and hypertensive lung, promoting wound healing, etc.

Description

technical field [0001] The invention relates to a method in the technical field of medical engineering, in particular to a method for synthesizing chitosan nucleophilic NO donor modified by quaternary ammonium salts. Background technique [0002] As a natural polymer material containing biological information, chitosan and its derivatives have both biocompatibility and biodegradability, and can be decomposed by lysozyme in organisms. When used in related medical fields, their safety is relatively high. Other synthetic materials are more reliable. The potential of chitosan as a biomedical material stems from its cationic character and high charge density in solution. The derivatization reaction of chitosan provides a new way to enhance the bioactivity and improve the mechanical properties of materials. The hydroxyl and amino groups in chitosan molecules are easy to chemically modify, and then can be made into various types of membranes, gels, polyelectrolytes and other mate...

Claims

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Application Information

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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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