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Active oxygen free radical sensitive cyclodextrin material as drug delivery carrier and preparation method thereof

A delivery carrier and cyclodextrin technology, which is applied in the direction of non-active components of polymer compounds, can solve the problems of limitations and lack of materials, and achieve the effects of simple preparation methods, easy large-scale synthesis, and good in vivo biocompatibility

Active Publication Date: 2014-04-30
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research work has only made limited progress, and materials with good safety and ideal ROS responsiveness are still lacking, which is the main bottleneck limiting the successful development of ROS-responsive drug delivery systems.

Method used

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  • Active oxygen free radical sensitive cyclodextrin material as drug delivery carrier and preparation method thereof
  • Active oxygen free radical sensitive cyclodextrin material as drug delivery carrier and preparation method thereof
  • Active oxygen free radical sensitive cyclodextrin material as drug delivery carrier and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Under nitrogen protection, 10mmol3-hydroxymethylbenzeneboronic acid and 15mmol pinacol were reacted in 60mL anhydrous tetrahydrofuran to obtain 3-hydroxymethylphenylboronic acid pinacol ester; 5mmol3-hydroxymethylphenylboronic acid pinacol ester was mixed with 10mmol N , N'-carbonyldiimidazole was reacted in 20 mL of anhydrous chloroform to obtain 3-imidazole carbonyloxy-phenylboronic acid pinacol ester; in the presence of 4 mmol 4-dimethylaminopyridine, 0.3 mmol α-cyclodextrin and 4 mmol 3-imidazole Carbonyloxy-phenylboronic acid pinacol ester was reacted in 15 mL of dimethyl sulfoxide at 20° C., and after 8 hours, the cyclodextrin material was obtained by precipitation in water, collected by centrifugation, and dried.

Embodiment 2

[0040] Under nitrogen protection, 10mmol 4-hydroxymethylbenzeneboronic acid and 20mmol pinacol were reacted in 50mL anhydrous dioxane to obtain 4-hydroxymethylphenylboronic acid pinacol ester; 5mmol4-hydroxymethylphenylboronic acid pinacol ester React with 15mmol N,N'-carbonyldiimidazole in 30mL of anhydrous dichloromethane to obtain 4-imidazole carbonyloxy-phenylboronic acid pinacol ester; in the presence of 4mmol N,N'-dicyclohexylcarbodiimide, 0.15mmol of β-cyclodextrin and 4mmol of 4-imidazolecarbonyloxy-phenylboronic acid pinacol ester were reacted in 12mL N,N-dimethylformamide at 30°C, and after 12 hours, they were collected by precipitation in water and centrifugation , and drying to obtain cyclodextrin material.

Embodiment 3

[0042]Under nitrogen protection, 10mmol3-hydroxymethylbenzeneboronic acid and 25mmol pinacol react in 60mL anhydrous acetonitrile to obtain 3-hydroxymethylphenylboronic acid pinacol ester; 8mmol3-hydroxymethylphenylboronic acid pinacol ester and 20mmol N , N'-carbonyldiimidazole was reacted in 25 mL of anhydrous ethyl acetate to obtain 3-imidazole carbonyloxy-phenylboronic acid pinacol ester; in the presence of 4.8 mmol N, N'-diisopropylcarbodiimide, 0.1 One mmol of γ-cyclodextrin reacted with 4.8 mmol of 3-imidazolecarbonyloxy-phenylboronic acid pinacol ester in 10 mL of N,N-dimethylacetamide at 40°C, and after 24 hours, it was collected by precipitation in water and centrifugation , and drying to obtain cyclodextrin material.

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Abstract

The invention aims to provide an active oxygen free radical sensitive cyclodextrin material as a drug delivery carrier. The chemical structure of the cyclodextrin material is disclosed in the specification, wherein n is equal to 6, 7 or 8 which are respectively corresponding to active oxygen free radical sensitive alpha-cyclodextrin, beta-cyclodextrin or gamma-cyclodextrin material; R is -H or disclosed in the specification; and the glucose unit of each cyclodextrin molecule at least has one R group disclosed in the specification. The invention also provides a preparation method of the cyclodextrin material.

Description

technical field [0001] The invention relates to an active oxygen free radical sensitive cyclodextrin material used as a drug delivery carrier and a preparation method thereof. Background technique [0002] In recent years, stimuli-responsive drug delivery systems have received extensive attention in the field of biomedicine. Such drug delivery systems can trigger the release of therapeutic drugs through the level of local chemical and biomolecules, including pH, reducing molecules and hydrolases [1]. Compared with the common delivery system, the responsive system has the following advantages: 1) Selective drug release at the lesion site; 2) Improved curative effect; 3) Reduced toxic and side effects; 4) Reduce the dosage by increasing the drug concentration at the lesion site; 5) Controlled drug release. Therefore, the research and development of stimuli-responsive drug controlled release system has always been the focus of interdisciplinary research in chemistry, material...

Claims

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Application Information

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IPC IPC(8): C08B37/16A61K47/40
Inventor 张建祥李晓辉张定林
Owner ARMY MEDICAL UNIV
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