A kind of cyclodextrin hyperbranched derivative and preparation method thereof

A cyclodextrin and derivative technology, applied in the field of cyclodextrin hyperbranched derivatives and their preparation, can solve the problems of insufficient hydrophilicity, loss of cationicity and consumption of beta-cyclodextrin derivatives, etc.

Active Publication Date: 2021-07-06
武汉恒创众利科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The β-cyclodextrin derivatives constructed by this method, on the one hand, have a relatively limited degree of hyperbranching, resulting in a limited number of hydroxyl values ​​that can be linked with small molecular amines; on the other hand, β-cyclodextrin hyperbranched Molecular amines are linked by urethane bonds. Each small molecular amine linked will consume one hydroxyl group, and small molecular amines will also consume one amino group.
This will inevitably lead to the loss of cationicity of β-cyclodextrin derivatives, and insufficient hydrophilicity, especially under high pH conditions.

Method used

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  • A kind of cyclodextrin hyperbranched derivative and preparation method thereof
  • A kind of cyclodextrin hyperbranched derivative and preparation method thereof
  • A kind of cyclodextrin hyperbranched derivative and preparation method thereof

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Effect test

Embodiment 1

[0046] In this embodiment, a cyclodextrin derivative and a preparation method thereof comprise the following steps:

[0047](1) Accurately weigh β-cyclodextrin (4.0g, 3.53mmol) and 18-crown-6 (6.6g, 25.0mmol) under inert gas protection conditions, dissolve in 150mL DMF, and then add KH (1.12g , 28.0mmol) and keep stirring to fully react with the hydroxyl group of cyclodextrin. The temperature was controlled at 50°C, and glycidol (15.0 g, 202.6 mmol) dissolved in 100 mL of DMF was slowly added dropwise to the above solution for about 24 hours. Control the temperature at 80°C and continue the reaction for 16h to end. After the temperature of the system was lowered to room temperature, a small amount of water was added to terminate the reaction, and the water was directly dialyzed (MWCO: 1000) and freeze-dried to obtain 17.1 g of β-cyclodextrin grafted hyperbranched polyglycerol;

[0048] (2) Take the β-cyclodextrin grafted hyperbranched polyglycerol obtained in the previous st...

Embodiment 2

[0051] In this embodiment, a cyclodextrin derivative and a preparation method thereof comprise the following steps:

[0052] (1) Accurately weigh β-cyclodextrin (4.0g, 3.53mmol) and 18-crown-6 (6.6g, 25.0mmol) under inert gas protection conditions, dissolve in 150mL DMF, and then add KH (1.12g , 28.0mmol) and keep stirring to fully react with the hydroxyl group of cyclodextrin. The temperature was controlled at 50°C, and glycidol (30.0 g, 405.2 mmol) dissolved in 100 mL of DMF was slowly added dropwise to the above solution for about 24 hours. Control the temperature at 80°C and continue the reaction for 16h to end. After the temperature of the system was lowered to room temperature, a small amount of water was added to terminate the reaction, and the water was directly dialyzed (MWCO: 1000) and freeze-dried to obtain 32.3g of β-cyclodextrin grafted hyperbranched polyglycerol;

[0053] (2) Take the β-cyclodextrin grafted hyperbranched polyglycerol obtained in the previous st...

Embodiment 3

[0056] In this embodiment, a cyclodextrin derivative and a preparation method thereof comprise the following steps:

[0057] (1) Accurately weigh α-cyclodextrin (3.43g, 3.03mmol) and 18-crown-6 (6.6g, 25.0mmol) under inert gas protection conditions, dissolve in 150mL DMF, and then add KH (1.12g , 28.0mmol) and keep stirring to fully react with the hydroxyl group of cyclodextrin. The temperature was controlled at 50°C, and glycidol (15.0 g, 202.6 mmol) dissolved in 100 mL of DMF was slowly added dropwise to the above solution for about 24 hours. Control the temperature at 80°C and continue the reaction for 16h to end. After the temperature of the system was lowered to room temperature, a small amount of water was added to terminate the reaction, and the water was directly dialyzed (MWCO: 1000) and freeze-dried to obtain 16.5g of β-cyclodextrin grafted hyperbranched polyglycerol;

[0058] (2) Disperse the α-cyclodextrin grafted hyperbranched polyglycerol obtained in the previo...

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Abstract

The invention discloses a cyclodextrin hyperbranched derivative and a preparation method thereof. First, cyclodextrin is used as a starting material to open ring glycidol under alkaline conditions to obtain cyclodextrin grafted hyperbranched polyglycerol; and then React cyclodextrin-grafted hyperbranched polyglycerol with epichlorohydrin to obtain cyclodextrin-grafted hyperbranched polyglyceryl glycidyl ether; The epoxy group on the hyperbranched polyglycerol glycidyl ether molecule is used to obtain the cyclodextrin hyperbranched derivative. By modifying the epoxy group on the cyclodextrin hyperbranched polyglycerol, and then using the amino ring-opening epoxy group on the small molecule amine to modify the small molecule amine, thereby retaining the cationic nature of the amino group, and at the same time the epoxy ring is opened to produce Hydroxyl groups, which ensure the hydrophilicity of the final cyclodextrin hyperbranched derivatives.

Description

technical field [0001] The invention relates to a cyclodextrin derivative and a preparation method thereof, in particular to a cyclodextrin hyperbranched derivative and a preparation method thereof. Background technique [0002] Cyclodextrin (CD) is a general term for cyclic oligosaccharides formed by 6 or more glucopyranose molecules forming a ring through α-1,4-glycosidic bonds, which can be acted on by cyclodextrin glucosyltransferase produced by starch. The most common are α-CD, β-CD, and γ-CD, which consist of 6, 7, and 8 glucopyranose units, respectively. Cyclodextrin is widely used in food, medicine, agriculture, cosmetics and other fields due to its unique truncated cone structure, which is hydrophilic on the outside and hydrophobic on the inside, and can form clathrates with specific molecules. [0003] There are strong hydrogen bonds between the molecules of CD, which limits the water solubility of cyclodextrin, and the ability to include and bind guest molecules...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C08G83/00C08B37/16A61K47/40
CPCA61K47/40C08B37/0012C08G83/005C08G83/006
Inventor杨斌陶丽尚同祎郑国栋陈晓明
Owner武汉恒创众利科技有限公司