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Pegylated glycosides of aerial parts of epimedium, and preparation and use thereof

A technology of PEGylation and icariin, which is applied in the direction of pharmaceutical formulations, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., and can solve problems such as poor water solubility, limited application, and reduced bioavailability question

Active Publication Date: 2010-09-29
北大世佳科技开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The water solubility of ICA is very poor, and the dosage form is usually oral preparation
Glycosides are easily hydrolyzed by gastric acid during oral administration, and their bioavailability decreases to varying degrees, which limits their clinical application

Method used

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  • Pegylated glycosides of aerial parts of epimedium, and preparation and use thereof
  • Pegylated glycosides of aerial parts of epimedium, and preparation and use thereof
  • Pegylated glycosides of aerial parts of epimedium, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 PEGylated icariin ICA-mPEG5000 was prepared by using polyethylene glycol monomethyl ether with a molecular weight of 5000.

[0018] Weigh 5.0g (1.0mmol) of polyethylene glycol monomethyl ether-5000 and dissolve it in 10mL of pyridine, then add 0.11g (1.1mmol) of succinic anhydride and 61mg (0.5mmol) of 4-dimethylaminopyridine (DMAP) ). The reaction was stirred at 50°C for 5h. After distilling off the solvent under reduced pressure, the residue was dried in vacuo and used directly in the next reaction. Take 336mg (~0.067mmol) of polyethylene glycol monomethyl ether-5000 derivative prepared above and 50mg (0.074mmol) of icariin and dissolve it in 2mL DMF, then add DCC28mg (0.14mmol) and DMAP9mg (0.074mmol) . After stirring at room temperature for 24 hours, the insoluble matter in the reaction solution was filtered off, and anhydrous ether was added to produce a white precipitate, which was filtered to obtain a light yellow solid. The product was further puri...

Embodiment 2

[0019] Example 2 PEGylated icariin ICA-mPEG2000 was prepared by using polyethylene glycol monomethyl ether with a molecular weight of 2000.

[0020] Repeat the preparation steps of Example 1, replace polyethylene glycol monomethyl ether-5000 with polyethylene glycol monomethyl ether-2000, and use a dialysis membrane with a cut-off molecular weight of 1000 to purify the product to obtain ICA-mPEG2000 with a yield of 78% . The solubility in water at room temperature is about 650mg / mL. The structure of this compound was confirmed by mass spectrum, nuclear magnetic resonance spectrum, infrared spectrum and so on. From 1 H-NMR spectrum calculates that the content of its icariin is 22%. Through gel exclusion chromatography (GPC) analysis, its Mn (number average molecular weight) is 3398, and Mw (weight average molecular weight) is 3708.

Embodiment 3

[0021] Example 3 PEGylated icariin ICA-mPEG750 was prepared by using polyethylene glycol monomethyl ether with a molecular weight of 750.

[0022] Repeat the preparation steps of Example 1, replace polyethylene glycol monomethyl ether-5000 with polyethylene glycol monomethyl ether-750, and use a dialysis membrane with a cut-off molecular weight of 500 to purify the product to obtain ICA-mPEG750 with a yield of 85% . The structure of this compound was confirmed by mass spectrum, nuclear magnetic resonance spectrum, infrared spectrum and so on. From 1 H-NMR spectrum calculated the content of icariin to be 47%. The solubility in water at room temperature is about 260mg / mL. The compound was analyzed by gel exclusion chromatography (GPC), and its Mn (number average molecular weight) was 2134, and its Mw (weight average molecular weight) was 2383.

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PUM

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Abstract

The invention relates to a pegylation preparation method of icariin which is an active ingredient of Chinese medicinal herbs, and application thereof. The pegylation icariin compound of the invention adopts the icariin as a matrix and as for the problem of poor water solubility of the icariin, polyethylene glycol with different molecular weights are used for carrying out modification to obtain the pegylation icariin compound with good water solubility, thus solving a plurality of key problems in the application of the icariin in clinic. The pegylation icariin compound of the invention can be used for preparing drugs for treating cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a preparation method of pegylation of icariin, an active ingredient of Chinese herbal medicine, and its application in the preparation of medicines for cardiovascular and cerebrovascular diseases. Background technique [0002] Icariin (icariin, ICA) is the main active ingredient of total flavonoids extracted from the stems and leaves of the Chinese herbal medicine Epimedium. ICA has a wide range of pharmacological effects, such as: regulating immunity, anti-tumor, anti-aging, and protecting the cardiovascular and cerebrovascular systems (for review articles, see: Chinese Patent Medicine, 2005, 27, 719-721; 954). Among them, anti-myocardial ischemia is one of the research hotspots that people pay more attention to in recent years. The water solubility of ICA is poor, and the dosage form is usually oral preparation. Glycosides are easily hydrolyzed by gastric acid during ora...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K31/7048A61K47/34A61P9/00A61K47/60
Inventor 周亚伟邢国文
Owner 北大世佳科技开发有限公司
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