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Curcumin-polysaccharide conjugate as well as preparation method and application thereof

A technology of curcumin and conjugates, which is applied in the field of biomedical materials to achieve the effects of mild synthesis conditions, high encapsulation efficiency, and low cost of raw materials

Inactive Publication Date: 2013-03-27
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the use of curcumin-polysaccharide conjugates as an oral absorption enhancer has no literature and patent reports at home and abroad

Method used

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  • Curcumin-polysaccharide conjugate as well as preparation method and application thereof
  • Curcumin-polysaccharide conjugate as well as preparation method and application thereof
  • Curcumin-polysaccharide conjugate as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0054] The synthesis of embodiment 1 curcumin-carboxymethyl chitosan

[0055] Add 0.1mol carboxymethyl chitosan to 10ml water, stir magnetically for 30min until completely dissolved, adjust the pH to about 6-7 with acetic acid, then add 0.5mol p-phenylenediamine, mix well and then add dropwise 0.2mol 1-ethyl -(3-Dimethylaminopropyl) carbodiimide (EDC) and 0.3mol hydroxysuccinimide (NHS), reacted at room temperature for 8 hours, dialyzed for 2 days, and freeze-dried to obtain carboxymethyl chitosan with free one-terminal amino group intermediate. Take the above intermediate and disperse it in 30ml of methanol, add 0.3mol of curcumin in methanol solution, ultrasonically reflux for 2h, the obtained crude product is washed repeatedly with absolute ethanol, anhydrous ether, and dichloromethane until the filtrate is colorless, and vacuum-dried to obtain purified curcumin-carboxymethyl chitosan conjugates.

Embodiment 2

[0056] The synthesis of embodiment 2 curcumin-heparin

[0057] Dissolve 2 mmol of heparin in formamide, add 8 mmol of ethylenediamine, stir magnetically for 2 min, then add 3 mmol of 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDC) and 4.5 mmol of hydroxysuccinimide Amine (NHS) was reacted at room temperature for 12 hours. After the reaction, acetone was added to precipitate the product, and the precipitate was obtained by suction filtration, redissolved in water, dialyzed for 2 days, and freeze-dried to obtain a heparin active intermediate with a free amino group at one end. Dissolve the heparin active intermediate obtained above in a methanol-water mixed solution, avoid light, and slowly add 6 mmol of curcumin in methanol solution dropwise under magnetic stirring at 50°C for 1.5 hours, and continue the reaction for 2 hours after the drop is completed Take the product by rotary evaporation to remove methanol, add a small amount of water to mix, and then filter with suction to...

Embodiment 3

[0058] The synthesis of embodiment 3 curcumin-hyaluronic acid

[0059] Dissolve 3mmol hyaluronic acid in tetrahydrofuran, add 10mmol m-phenylenediamine, stir magnetically for 5min, then add 4.5mmol 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDC) and 6mmol hydroxysuccinate Imide (NHS) was reacted at room temperature for 12 hours. After the reaction, acetone was added to precipitate the product, and the precipitate was obtained by suction filtration, redissolved in water, dialyzed for 2 days, and freeze-dried to obtain the active intermediate of hyaluronic acid with a free terminal amino group. Take the hyaluronic acid active intermediate obtained above and dissolve it in methanol-water mixed solution, avoid light, and slowly add 9 mmol of curcumin methanol solution dropwise under magnetic stirring at 50°C. The dropping time is 2 hours, and continue to react for 1 hour after the dropping , take the product by rotary evaporation to remove methanol, add a small amount of water ...

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Abstract

The invention relates to a curcumin-polysaccharide conjugate as well as a preparation method and application thereof. The preparation method comprises the following steps of: grafting amino acid at one terminal of a diamine compound to polysaccharide through amidation to obtain a polysaccharide macromolecule with a free terminal of amino acid; and introducing curcumin on the polysaccharide frame by a Schiff base reaction. The preparation method is characterized in that 1, the water solubility and in-vivo and in-vitro stability of the curcumin can be improved due to grafting modification on the curcumin, and the generated curcumin-polysaccharide conjugate can be used as a novel macromolecular medicament indepterminalently; 2, the curcumin-polysaccharide conjugate has a strong oral absorption promoting effect, is high in safety, and can achieve the effects of promoting medicament absorption, improving the curative effect, reducing the toxic and side effect of the conjugate and the like; and 3, the amphipathy of the polysaccharide molecule is improved by introducing the hydrophobic group curcumin, so that the curcumin-polysaccharide conjugate can be self-assembled into nano-micelle, and can be used as a vector of an insoluble medicament. The preparation method is simple, low in cost, and applicable to large-scale continuous production.

Description

[0001] Technical field: the invention belongs to the field of biomedical materials, in particular to the preparation method and application of curcumin-polysaccharide conjugates. Background technique: [0002] Curcumin (curcumin) is a flavonoid extracted from the rhizome of Zingiberaceae, soluble in organic solvents such as methanol, ethanol, acetic acid, acetone and chloroform and alkaline water, and extremely soluble in neutral to acidic aqueous solutions. Low. Curcumin has a wide range of sources, low price, high efficiency and low toxicity, and has great medicinal research value. In addition to its anti-oxidation, anti-inflammatory, anti-cancer, free radical scavenging, anti-microbial, and pharmacological effects on the cardiovascular system and digestive system, recent studies have found that curcumin may also be through a variety of mechanisms (down-regulation of MDR1, survivin mRNA expression and P-gp, survivin protein expression, promote tumor cell apoptosis, etc.) re...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K47/36A61K31/12A61K9/14A61K9/19A61P35/00A61P39/06A61P29/00
Inventor 周建平姚静倪江杨晖
Owner CHINA PHARM UNIV
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