Temperature-sensitive amphiphilic cyclodextrin polymer as well as preparation method and application

A cyclodextrin polymer and amphiphilic technology, which is applied in the field of medicine, can solve the problems of limited hydrophobic space and limited inclusion effect, and achieve the effect of simple synthesis steps, improved encapsulation efficiency and drug loading capacity

Active Publication Date: 2012-01-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The linear cyclodextrin polymer is connected to the polymer chain through only one hydroxyl group, the change of the ring structure is small, and the inclusion effect can be maintained, but the inclusion ability of the cyclodextrin is affected by the matching degree between the cavity and the hydrophobic drug, and the inclusion effect limited, and the hydrophobic space formed by the PCEC triblock copolymer is also very limited

Method used

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  • Temperature-sensitive amphiphilic cyclodextrin polymer as well as preparation method and application
  • Temperature-sensitive amphiphilic cyclodextrin polymer as well as preparation method and application
  • Temperature-sensitive amphiphilic cyclodextrin polymer as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of PCEC-β-CD copolymer

[0039] (1) Synthesis of PCEC 1000-6000-1000 :

[0040] Configure Sn(Oct) 2 Toluene solution 0.3g / ml. Weigh the PEG after dewatering and purification 600 0 9.0g, CL 3.0g, add Sn(Oct) 2 0.1ml of toluene solution was placed in a 100ml round bottom flask, protected by nitrogen, and reacted in an oil bath at 130°C for 24 hours. After the reaction was completed, the temperature of the reaction flask was lowered to room temperature, and the reaction product was dissolved in 6 ml of anhydrous dichloromethane, then magnetically stirred and precipitated in 200 ml of diethyl ether, filtered and sucked dry. The product was redissolved, filtered and drained, repeated twice, and placed in a vacuum oven overnight to evaporate the residual ether to obtain the final product PCEC.

[0041] PCEC 1000-6000-1000 For NMR and IR spectra see figure 1 with figure 2 , the productive rate is 90.2%, the molecular weight calculated by N...

Embodiment 2

[0051] Example 2: Preparation of indomethacin PCEC-β-CD drug-loaded hydrogel and investigation of its release behavior

[0052] Weigh PCEC-β-CD1g, indomethacin 100mg, dissolve in 1ml DMF, dissolve evenly and transfer to the dialysis bag. Dialyze in 1L of deionized water at 80°C for 24 hours, changing the solution every two hours. After the dialysis is complete, transfer the gel formed in the dialysis bag to a 10ml graduated cylinder, add water to the 3ml mark, and mix well to obtain a drug-loaded hydrogel of a certain concentration. 0.5ml of the hydrogel was freeze-dried, reconstituted with DMF to measure the drug loading and encapsulation efficiency, and the rest of the indomethacin drug-loaded hydrogel was stored at 4°C.

[0053] PCEC-β-CD uses DMF as solvent, the obtained drug loading is 3.01%, and the encapsulation efficiency is 67.4%.

[0054] Separately weigh 500 mg of PCEC-β-CD, add 1.5 ml of deionized water to dissolve evenly, and form a hydrogel. Weigh 8.4 mg of in...

Embodiment 3

[0057] Example 3: Preparation of indomethacin PCEC-β-CD drug-loaded hydrogel

[0058] Weigh 500 mg of PCEC-β-CD and 50 mg of indomethacin, dissolve them in 500 μl DMSO, and transfer them to the dialysis bag after uniform dissolution. The dialysis method and the method for calculating the drug loading are the same as in Example 2. PCEC-β-CD uses DMSO as a solvent, the ratio of drug to material is 1:10, and the ratio of DMSO to material is 1:1 (ml / g). The content is 5.17%, and the encapsulation efficiency is 51.7%.

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Abstract

The invention provides a temperature-sensitive amphiphilic cyclodextrin polymer PCEC (polycaprolactone-polyethylene glycol-polycaprolactone, PCL-PEG-PCL). The polymer provided by the invention is the amphiphilic cyclodextrin polymer which is obtained by linking a PCL-PEG-PCL molecule with beta-CD (cyclodextrin) through utilizing the temperature-sensitive characteristic of a PCL-PEG-PCL triblock copolymer and the inclusion effect of beta-CD on a hydrophobic medicament, can effectively load and slowly release a hydrophobic or water-soluble medicament on the basis of the traditional hydrogel encapsulated water-soluble medicament, has proper critical gel temperature and can form in situ temperature-sensitive hydrogel after injection. According to the invention, the hydrophobic zone of the polymer is obviously enlarged, thereby effectively improving the loading capacity of the hydrogel on the hydrophobic medicament and obtaining high medicament encapsulation rate and medicament loading amount; and simultaneously, the controlled-release effect of the medicament after local injection delivery is realized by utilizing the temperature-sensitive gel performance of the polymer. The polymer provided by the invention has the following chemical structure shown in the specification.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a biodegradable copolymer combined with cyclodextrin and capable of carrying hydrophobic drugs and its temperature-sensitive hydrogel, and its application in the preparation of local injection drug carriers. Background technique [0002] In recent years, many studies have been devoted to the development of injectable temperature-sensitive hydrogels, which are usually in the form of flowing solutions at room temperature or slightly higher than body temperature, and are convenient for mixing with various small-molecule drugs or bioactive substances, even microspheres, Physical mixing of nanoparticles, etc.; when the solution is injected into the subcutaneous tissue or muscle tissue, its physical state rapidly transforms into a gel due to temperature changes, thereby allowing the drug to be released slowly at the administration site [1，2] . This characteristic of injectable ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08B37/16C08G63/91C08G63/664A61K47/48
Inventor 邱利焱魏霞蔚吕辛怡
Owner ZHEJIANG UNIV
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