Functionalized icariin derivatives, and preparation method and application thereof

An icariin, functionalized technology, applied in the field of biomedical materials, can solve problems such as limited loading, and achieve the effects of slowing the release rate, low cytotoxicity, and good water solubility

Active Publication Date: 2015-03-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the concentration of Ica is greater than 1×10 -5 M has obvious cytotoxicity. Although the solubility of Ica is low, the concentration of the saturated solution obtained at room temperature can reach 2×10 -5 M, has obvious inhibitory effect on cell growth
In order to improve the bioavailability of Ica and avoid the problems of initial burst release and limited loading in non-covalent loading methods, it is necessary to covalently introduce Ica into tissue engineering scaffolds, but the chemical properties of Ica are relatively stable and are not prone to occurrence. The active group of the reaction is difficult to react with other substances in a covalent form, and can only be loaded into the scaffold material in a non-covalent form

Method used

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  • Functionalized icariin derivatives, and preparation method and application thereof
  • Functionalized icariin derivatives, and preparation method and application thereof
  • Functionalized icariin derivatives, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Using icariin and succinic anhydride as raw materials, the molar ratio of icariin and succinic anhydride is 1:10.8.

[0047] Weigh 200mg of icariin and dissolve it in 2ml of pyridine, weigh 320mg of succinic anhydride and dissolve it in 2ml of pyridine, add the succinic anhydride solution to the icariin solution dropwise under stirring, mix well, and react at 25°C After 12 hours, most of the solvent was distilled off under reduced pressure in a rotary evaporator after the reaction was over to obtain a light yellow paste solid, which was dissolved in 20 mL of organic extractant ethyl acetate, then added 50 mL of deionized water, at 60 Stir and wash at ℃ for 15 minutes, let stand to separate the layers, separate the water layer with a separatory funnel, then add 50ml deionized water to the ethyl acetate layer containing the derivative to wash, repeat the operation several times until the pH value of the water layer tends to neutral. Then the ethyl acetate layer was trans...

Embodiment 2

[0050] Weigh 200mg of icariin and dissolve it in 2ml of pyridine, weigh 320mg of succinic anhydride and dissolve it in 2ml of pyridine, add the succinic anhydride solution to the icariin solution dropwise under stirring, mix well, and react at 25°C After 4 hours, most of the solvent was removed by distillation under reduced pressure in a rotary evaporator after the reaction was over to obtain a light yellow paste solid, which was dissolved with 20 mL of organic extractant ethyl acetate, then added 50 mL of deionized water, at 60 Stir and wash at ℃ for 15 minutes, let stand to separate the layers, separate the water layer with a separatory funnel, then add 50ml deionized water to the ethyl acetate layer containing the derivative to wash, repeat the operation several times until the pH value of the water layer tends to neutral. Then the ethyl acetate layer was transferred, and the ethyl acetate was volatilized in an ultra-clean bench, and then freeze-dried with a freeze dryer fo...

Embodiment 3

[0052] Using icariin and succinic anhydride as raw materials, the molar ratio of icariin and succinic anhydride is 1:10.8.

[0053] Weigh 200mg of icariin and dissolve it in 2ml of pyridine, weigh 320mg of succinic anhydride and dissolve it in 2ml of pyridine, add the succinic anhydride solution dropwise into the icariin solution and mix evenly under stirring, and stir at 40°C React for 4 hours. After the reaction was completed, most of the solvent was evaporated in an ultra-clean bench window to obtain a light yellow paste solid. Dissolve the obtained paste solid with 20mL of organic extractant ethyl acetate, then add 50ml of deionized water, stir and wash at 60°C for 15min, after standing for layers, separate the water phase with a separatory funnel, and then pour it into the derivative containing 50 ml of deionized water was added to the ethyl acetate layer for washing, and the operation was repeated several times until the pH value of the aqueous phase tended to be neutra...

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Abstract

The invention discloses functionalized icariin derivatives, namely succinic acid icariin and maleic acid icariin, wherein a structural formula of the succinic acid icariin is as shown in the specification; and the structural formula of the maleic acid icariin is as shown in the specification. The preparation method comprises the following steps: respectively dissolving icariin and anhydride serving as raw materials into a polar solvent according to the molar ratio of 1 to (2-11), so as to form a liquid; mixing two liquids evenly under stirring, and then reacting at 25-40 DEG C for 4-24 hours; removing the polar solvent, residual anhydride and a decomposition product of the residual anhydride after reaction is ended, so as to obtain a reaction product; and freezing and drying the reaction product, so as to obtain the functionalized icariin derivatives. The functionalized icariin derivatives disclosed by the invention have good water solubility and low cytotoxicity; Ica can be loaded into a tissue engineer scaffold material in a covalent form; and the functionalized icariin derivatives can be applied to the tissue engineering as bio-active substances.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and relates to an icariin derivative, a preparation method thereof, and an application of the icariin derivative in tissue engineering. Background technique [0002] Tissue engineering is currently the most promising technology for defect tissue repair and functional reconstruction. Artificial tissue or pre-tissue is composed of scaffolds made of biomaterials and seed cells. The former provides the latter with a supporting environment for adhesion, proliferation, differentiation and organization. , and finally together form artificial tissue or pre-tissue with certain shape and function. However, only by compounding the seed cells and the scaffold, the cell growth lacks effective regulation, and finally it is difficult to form the desired target tissue. The main reason is that the scaffold material itself has a limited role in promoting cell differentiation and anabolism, and the formation of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00A61L27/54
CPCA61L27/54A61L2300/232C07H1/00C07H17/07
Inventor 肖玉梅何龙杨继榕鲁建李东晓张兴栋
Owner SICHUAN UNIV
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