A kind of cyclodextrin derivative and its preparation method and application

A cyclodextrin and derivative technology, applied in the field of drug carriers, can solve the problems of healthy tissue and cytotoxic side effects, lack of tumor targeting, low solubility, etc., and achieve excellent physical and chemical properties, good biocompatibility, biological good compatibility

Active Publication Date: 2021-04-30
HARBIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some chemotherapeutic drugs that have been developed so far have problems such as low solubility, poor stability, easy multidrug resistance, lack of tumor targeting, and local or systemic side effects on healthy tissues and cells, which greatly limit their clinical applications. Therefore, it is particularly important to develop new, low-toxicity and high-efficiency drug delivery systems

Method used

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  • A kind of cyclodextrin derivative and its preparation method and application
  • A kind of cyclodextrin derivative and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0039] (1) Preparation of arginine active ester:

[0040] Weigh 220mgEDC, 8mgDMAP, and 300mgFmoc-Arg(pbf)-OH respectively, mix them in a three-necked flask, stir and activate them at room temperature in the dark for 2-4h, and obtain arginine active ester solution double protected by Fmoc and pbf;

[0041] (2) Preparation of biotin active ester:

[0042] Dissolve 30 mg of biotin, 50 mg of EDC and 60 mg of NHS in 5 ml of DMF at the same time, stir and activate at room temperature for 12-14 hours in the dark to obtain biotin active ester solution;

[0043] (3) Preparation of Fmoc and pbf double-protected arginine-modified hydroxypropyl-β-cyclodextrin:

[0044] Take 150mg of hydroxypropyl-β-cyclodextrin and dissolve it in 10ml of DMF to obtain a solution of hydroxypropyl-β-cyclodextrin, add Fmoc and pbf double-protected arginine active ester solution, and stir at room temperature in the dark 48h, after the reaction is over, remove the reaction solvent, add acetone and stir for 1...

Embodiment 2

[0052] (1) preparing a cyclodextrin solution: dissolving the cyclodextrin in a solvent to obtain a cyclodextrin solution;

[0053] (2) Preparation of amino acid activated ester: Dissolve Fmoc-arginine (pbf)-OH in a solvent, add a catalyst, mix, control the temperature at 60°C, and stir for 24 hours to obtain arginine activated ester;

[0054] (3) Preparation of biotin-activated ester: dissolve biotin in a solvent, add a catalyst to mix, control the temperature at 60°C, and react under stirring for 96 hours to obtain biotin-activated ester;

[0055] (4) Add the arginine activated ester solution to the cyclodextrin solution under stirring conditions, control the temperature at 60°C, and react for 96 hours; after the reaction is completed, remove the reaction solvent, add acetone and stir for 48 hours, and filter to remove the acetone , to obtain a white powdery crude product; the crude product is recrystallized in water to obtain Fmoc-arginine (pbf) modified cyclodextrin;

[00...

Embodiment 3

[0071] (1) preparing a cyclodextrin solution: dissolving the cyclodextrin in a solvent to obtain a cyclodextrin solution;

[0072] (2) Preparation of amino acid activated ester: Dissolve Fmoc-lysine-OH in a solvent, add catalyst, after mixing, control the temperature at 40°C, stir and react for 18 hours to obtain amino acid activated ester;

[0073] (3) Preparation of biotin-activated ester: dissolve biotin in a solvent, add a catalyst to mix, control the temperature at 40°C, and react for 58 hours under stirring to obtain biotin-activated ester;

[0074] (4) Under stirring conditions, add the lysine activated ester solution to the cyclodextrin solution, control the temperature at 40°C, and react for 48 hours; after the reaction is completed, remove the reaction solvent by rotary evaporation of the mixed solution, then add acetone and stir for 36 hours , remove acetone by filtration to obtain a white powdery crude product; recrystallize the crude product in water to remove cyc...

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Abstract

The invention relates to the technical field of drug carriers, in particular to a derivative of cyclodextrin and its preparation method and application. The derivative is composed of biotin, amino acid and cyclodextrin substances, and is used for drug delivery, medicine and hygiene, etc. In the field, it is used as a drug carrier, carrying bioactive ingredients, and has the characteristics of good biocompatibility and tumor targeting.

Description

technical field [0001] The present invention relates to the technical field of drug carriers, in particular to a cyclodextrin derivative and its preparation method and application, especially to a cyclodextrin derivative modified by biotin and amino acid, and its application in drug delivery and medical care Applications. Background technique [0002] Cyclodextrin is a cyclic oligosaccharide compound composed of 6-12 D-glucose molecules connected by 1,4-glucosidic bonds. Its structure is a hollow cylinder, and the outer surface is hydrophilic due to the presence of hydroxyl groups. characteristics, and the hydrophobic cavity has inclusion ability for various guest molecules. The inclusion of cyclodextrin and its derivatives can not only change the physical and chemical properties of the drug, increase the solubility of the drug, reduce the stimulation of the drug to the human body, and even change the behavior of the drug in the body. In addition, cyclodextrin and its deri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K31/337A61K47/54A61K47/69A61P35/00
CPCA61K31/337A61K47/542A61K47/557A61K47/6951A61P35/00C08B37/0012
Inventor 梁娜孙少平闫彩霞
Owner HARBIN NORMAL UNIVERSITY
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