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Cyclodextrin-base nitric oxide donor and method for preparing same

A technology of nitric oxide and cyclodextrin, which is applied in cardiovascular system diseases, antineoplastic drugs, drug combinations, etc., can solve the problems of short half-life and poor stability, and achieve long half-life, good stability, and rapid endothelialization Effect

Inactive Publication Date: 2018-05-29
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention provides a cyclodextrin-based nitric oxide donor that uses cyclodextrin as a raw material to synthesize a cyclodextrin-based nitric oxide donor with good stability, high-efficiency endocytosis by cells, and targeted release of nitric oxide, which solves the problem of traditional nitric oxide donors. Problems of poor stability and short half-life

Method used

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  • Cyclodextrin-base nitric oxide donor and method for preparing same
  • Cyclodextrin-base nitric oxide donor and method for preparing same
  • Cyclodextrin-base nitric oxide donor and method for preparing same

Examples

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Comparison scheme
Effect test

Embodiment 1

[0048] Suspend 60g of β-cyclodextrin in 500mL of water, add 7g of saturated sodium hydroxide solution dropwise at 0°C until the solution is clear and transparent; keep 0°C, dissolve 15g of p-toluenesulfonyl chloride in 10mL of acetonitrile, dropwise Add the above solution, react at room temperature for 2 hours; place at 4°C overnight, filter the solid with suction and recrystallize with water 3 times to obtain β-cyclodextrin activated by p-toluenesulfonyl chloride, see figure 1 .

[0049] Dissolve 1.5g of β-cyclodextrin activated by p-toluenesulfonyl chloride in 20mL of DMF, heat to 80°C, add 3.5mL of triethylenetetramine and 2mL of triethylamine in sequence; after 48 hours of reaction, precipitate with ether three times, white The solid was dried in a vacuum oven to obtain an aminated β-cyclodextrin, see figure 2 .

[0050] Dissolve 3.5g of D-penicillamine in 20mL of dimethyl sulfoxide, cool to 0°C, add 15mL of acetic anhydride in dimethyl sulfoxide dropwise, keep at -20°C...

Embodiment 2

[0054] Suspend 60g of α-cyclodextrin in 500mL of water, add 7g of saturated sodium hydroxide solution dropwise at 0°C until the solution is clear and transparent; keep 0°C, dissolve 15g of p-toluenesulfonyl chloride in 10mL of acetonitrile, Add the above solution, react at room temperature for 2 hours; place at 4°C overnight, filter the solid with suction and recrystallize 3 times with water to obtain α-cyclodextrin activated by p-toluenesulfonyl chloride.

[0055] Dissolve 3 g of α-cyclodextrin activated by p-toluenesulfonyl chloride in 25 mL of DMF, heat to 80 ° C, add 3 mL of ethylenediamine and 2 mL of 4-dimethylaminopyridine in sequence, react for 24 hours, and precipitate three times with acetonitrile, white solid Dry in a vacuum oven to obtain aminated α-cyclodextrin.

[0056] Dissolve 5g of D-penicillamine in 20mL of DMF, add 15mL of acetic anhydride in DMF dropwise, and keep it at 80°C for 2 hours. After the reaction is complete, remove the solvent with a rotary evapo...

Embodiment 3

[0060] Suspend 60g of α-cyclodextrin in 500mL of water, add 7g of saturated sodium hydroxide solution dropwise at 0°C until the solution is clear and transparent; keep 0°C, dissolve 15g of p-toluenesulfonyl chloride in 10mL of acetonitrile, Add the above solution, react at room temperature for 2 hours; place at 4°C overnight, filter the solid with suction and recrystallize 3 times with water to obtain α-cyclodextrin activated by p-toluenesulfonyl chloride.

[0061] Dissolve 3 g of cyclodextrin activated by p-toluenesulfonyl chloride in 25 mL of DMF, heat to 80 °C, and add 3 mL of NH 2 -CH 2 CH=CHCH 2 -NH 2 and 2 mL of triethylamine, reacted for 36 hours, precipitated with methanol three times, and dried the white solid in a vacuum oven to obtain aminated α-cyclodextrin.

[0062] Dissolve 15g of D-penicillamine in 20mL of toluene, add 150mL of acetic anhydride in toluene drop by drop, keep the reaction at 60°C for 20 hours, after the reaction is complete, remove the solvent ...

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Abstract

The invention discloses a cyclodextrin-base nitric oxide donor and a method for preparing the same. The cyclodextrin-base nitric oxide donor is shown as a formula (I). The method includes dissolving reaction products of amination cyclodextrin and N-acetyl penicillamine thiolactone in organic solvent; adding nitroso tert-butyl ester into the organic solvents; carrying out complete reaction under certain conditions and then precipitating reaction products by the aid of poor solvents to obtain the cyclodextrin-base nitric oxide donor. The cyclodextrin-base nitric oxide donor and the method have the advantages that the cyclodextrin-base nitric oxide donor prepared by the aid of the method can be widely applied to medicine development, for example, the cyclodextrin-base nitric oxide donor can be used for preparing subcutaneous, intramuscular or intravenous injection, the subcutaneous, intramuscular or intravenous injection can be used for treating cardiovascular diseases, tumor and the like, accordingly, excellent treatment effects can be realized, and the cyclodextrin-base nitric oxide donor and the method have popularization and application value.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a cyclodextrin nitric oxide donor and a preparation method thereof. Background technique [0002] Nitric oxide (NO) is an important messenger molecule and effector molecule in living organisms. It can participate in the regulation of various physiological functions in living organisms and play extremely important functions in vivo. For example, nitric oxide is involved in processes such as vascular regulation, neurotransmission, inflammation and immune response. Nitric oxide can induce apoptosis of macrophages, cardiomyocytes, vascular smooth muscle cells, and pancreatic islet cells. In addition, a large number of studies have shown that nitric oxide is closely related to tumors. Low concentrations of nitric oxide can promote tumor growth, while high concentrations of nitric oxide can inhibit tumor growth. [0003] In order to overcome the insufficiency of nitric ...

Claims

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Application Information

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IPC IPC(8): C08B37/16A61K31/724A61P9/00A61P35/00
CPCC08B37/0012A61K31/724
Inventor 计剑金桥贾凡邓永岩
Owner ZHEJIANG UNIV
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