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 material shortage and limitation, and achieve the effects of simple preparation method, easy large-scale synthesis, and good in vivo biocompatibility

Active Publication Date: 2016-04-13
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
Comparison scheme
Effect test

Embodiment 1

[0038] Under the protection of nitrogen, 10mmol 3-hydroxymethylphenylboronic acid and 15mmol pinacol are reacted in 60mL anhydrous tetrahydrofuran to obtain 3-hydroxymethylphenylboronic acid pinacol ester; 5mmol 3-hydroxymethylphenylboronic acid pinacol ester and 10mmolN, N'-carbonyldiimidazole was reacted in 20mL anhydrous chloroform to obtain 3-imidazolecarbonyloxy-phenylboronic acid pinacol ester; in the presence of 4mmol 4-dimethylaminopyridine, 0.3mmol α-cyclodextrin and 4mmol 3-imidazolecarbonyl The oxy-phenylboronic acid pinacol ester was reacted in 15 mL of dimethyl sulfoxide at 20°C. After 8 hours, the cyclodextrin material was obtained by precipitation in water, centrifugal collection, and drying.

Embodiment 2

[0040] Under the protection of nitrogen, 10mmol 4-hydroxymethylphenylboronic acid and 20mmol pinacol are reacted in 50mL anhydrous dioxane to obtain 4-hydroxymethylphenylboronic acid pinacol ester; 5mmol 4-hydroxymethylphenylboronic acid pinacol ester React with 15mmolN,N'-carbonyldiimidazole in 30mL anhydrous dichloromethane to obtain 4-imidazolecarbonyloxy-phenylboronic acid pinacol ester; in the presence of 4mmolN,N'-dicyclohexylcarbodiimide, 0.15mmolβ -Cyclodextrin and 4mmol 4-imidazolecarbonyloxy-phenylboronic acid pinacol ester were reacted in 12mL N,N-dimethylformamide at 30°C. After 12 hours, it was precipitated in water, collected by centrifugation, and dried. The cyclodextrin material is obtained.

Embodiment 3

[0042] Under the protection of nitrogen, 10mmol 3-hydroxymethylphenylboronic acid and 25mmol pinacol are reacted in 60mL anhydrous acetonitrile to obtain 3-hydroxymethylphenylboronic acid pinacol ester; 8mmol 3-hydroxymethylphenylboronic acid pinacol ester and 20mmolN, N'-carbonyldiimidazole was reacted in 25mL of anhydrous ethyl acetate to obtain 3-imidazolecarbonyloxy-phenylboronic acid pinacol ester; in the presence of 4.8mmol N,N'-diisopropylcarbodiimide, 0.1mmolγ- Cyclodextrin was reacted with 4.8mmol of 3-imidazolecarbonyloxy-phenylboronic acid pinacol ester in 10mL N,N-dimethylacetamide at 40°C. After 24 hours, it was precipitated in water, collected by centrifugation, and dried. The cyclodextrin material is obtained.

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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 as a drug delivery carrier and a preparation method thereof. Background technique [0002] In recent years, stimulus-responsive drug delivery systems have received extensive attention in the field of biomedicine. This type of drug delivery system can trigger the release of therapeutic drugs through the level of local chemical and biological molecules, including pH, reducing molecules, and hydrolytic enzymes [1]. Compared with ordinary delivery systems, the responsive system has the following advantages: 1) selective release of drugs at the lesion site; 2) improved efficacy; 3) reduction of toxic and side effects; 4) reduction of the administered dose by increasing the concentration of the drug at the lesion site; 5) Controllable drug release. Therefore, the research and development of stimulus-responsive drug controlled release systems has always been the focus of inter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K47/40
Inventor 张建祥李晓辉张定林
Owner ARMY MEDICAL UNIV
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