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Application of cyclodextrin-methyl vinyl ether/maleic anhydride copolymer and self-assembled nanoparticle of copolymer in oral medicine delivery

A technology of methyl vinyl ether and maleic anhydride, which is applied in the direction of non-active components of polymer compounds and powder delivery, can solve the problems of poor transmembrane absorption capacity and limited solubilization ability of insoluble drugs, and improve oral administration. Bioavailability, reduced first-pass effect, good stability

Active Publication Date: 2015-03-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cyclodextrin has poor transmembrane absorption ability in the gastrointestinal tract and limited solubilization ability for poorly soluble drugs

Method used

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  • Application of cyclodextrin-methyl vinyl ether/maleic anhydride copolymer and self-assembled nanoparticle of copolymer in oral medicine delivery
  • Application of cyclodextrin-methyl vinyl ether/maleic anhydride copolymer and self-assembled nanoparticle of copolymer in oral medicine delivery
  • Application of cyclodextrin-methyl vinyl ether/maleic anhydride copolymer and self-assembled nanoparticle of copolymer in oral medicine delivery

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] CD-PVM / MA was synthesized from hydroxypropyl β-cyclodextrin (HP-β-CD) and PVM / MA (molecular weight: 200,000).

[0034] Dissolve PVM / MA and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) in acetone / tetrahydrofuran (3 / 2, v / v), ice bath After activating for 2 hours, add HP-β-CD (36 times the molar weight of PVM / MA), react at room temperature (25°C) and nitrogen protection for 3 hours, and obtain a white powder after separation and purification, which is CD-PVM / MA. The reaction formula is as follows:

[0035]

Embodiment 2

[0037] The molecular weight of PVM / MA in the reaction formula ranges from 100,000 to 2.5 million, and the cyclodextrin can be α, β, γ cyclodextrin and their derivatives.

[0038] Determination by NMR 1 HNMR hydrogen spectrum to determine the structure of CD-PVM / MA in embodiment 1, PVM / MA and CD-PVM / MA are solvent with deuterium band dichloromethane, HP-β-CD is solvent with heavy water, the results see figure 2 . The signal peak of CD is attributed to 3.5-4.0ppm (hydroxyglucose ring C3, 4, 5, 6 methine); the PVM / MA signal peak is assigned as follows: 3.567ppm (methine on the parent chain), 2.513ppm ( ester group), 2.181 ppm (hydrogen on cyclic anhydride). Compared with the NMR spectrum of PVM / MA, the NMR spectrum of cyclodextrin-grafted PVM / MA has a split peak (signal peak of hydroxyl cyclodextrin) at 3.5-4.0ppm, and the NMR spectrum shifts to the high field, indicating that cyclodextrin Grafted onto PVM / MA.

Embodiment 3

[0040] Adopt infrared spectrum to determine the structure of CD-PVM / MA in embodiment 1, select KBr to be blank auxiliary material for use, the result is as follows image 3 . Comparing the infrared spectra of CD-PVM / MA and PVM / MA, it can be seen that the position and intensity of the characteristic peaks of the infrared spectra changed significantly before and after cyclodextrin was grafted on PVM / MA. The peaks at 1782, 1729, and 1250 become blunt and the signal weakens (cyclic anhydride C=O signal peak, the number of cyclic anhydrides decreases). Since the two compounds are high molecular weight polymers, the hydrolysis of cyclic anhydride and the grafting of cyclodextrin are incomplete, so some characteristic peaks of PVM / MA still remain in the infrared spectrum of CD-PVM / MA. Infrared spectra showed that cyclodextrin was successfully grafted onto PVM / MA, and the grafting rate was high.

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Abstract

The invention relates to synthesis of an amphipathic polyanhydride carrier material and application of self-assembled nanoparticles of the amphipathic polyanhydride carrier material in medicine delivery. The amphipathic polyanhydride carrier material is prepared by taking amphipathic cyclodextrin and a derivative of the amphipathic cyclodextrin as a hydrophilic end together an ester bond and a hydrophobic methyl vinyl ether / maleic anhydride copolymer. The carrier material has double inhibition function of biological adhesion and excretion protein (P-gp) and metabolic enzyme (CYP450), the lymph transfer of medicines is promoted, the first pass effect of livers can be reduced, the remarkable increase of oral bioavailability is finally achieved, and wide application prospect is achieved.

Description

technical field [0001] The invention belongs to the field of new auxiliary materials and new dosage forms of pharmaceutical preparations, and relates to a multifunctional polyanhydride carrier material cyclodextrin-methyl vinyl ether / maleic anhydride copolymer and its application in oral delivery of insoluble drugs. Background technique [0002] To date, oral administration remains the preferred route, thanks to its good patient compliance. However, many candidate drugs are difficult to obtain ideal oral absorption due to factors such as the destruction of gastric acid, mucus layer retention and penetration, regulation of drug permeability by efflux proteins, and systemic pre-metabolism (intestinal and hepatic first-pass metabolism). , unable to achieve clinical application. In view of the complexity of oral delivery, the combined application of multiple strategies is often required to significantly improve the oral bioavailability of drugs. [0003] Cyclodextrin (CD) is a...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08B37/16C08J3/12A61K47/40A61K9/14
Inventor 孙进何仲贵张栋潘小磊
Owner SHENYANG PHARMA UNIVERSITY
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