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Selenium-containing curcumin polymer and its preparation method and application

A technology of selenium-curcumin and curcumin derivatives, which is applied in the field of water-soluble selenium-containing curcumin high molecular polymers and its preparation, and can solve the problems of complex preparation process, high cost, and large amount of co-solvent used

Active Publication Date: 2012-07-11
浙江益弹新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have many disadvantages such as low loading rate of curcumin, poor drug storage stability, large amount of emulsifier and cosolvent used, safety problems in intravenous injection, complex preparation process, high cost, etc.
Although there have been reports in the literature that curcumin and polyethylene glycol are linked by carbamate bonds or peptide bonds to form water-soluble curcumin derivatives and used for anti-tumor reports, but these derivatives are not stable enough to be used in blood. Unstable in circulation, clears quickly

Method used

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  • Selenium-containing curcumin polymer and its preparation method and application
  • Selenium-containing curcumin polymer and its preparation method and application
  • Selenium-containing curcumin polymer and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of polycondensation product shown in formula (II)

[0050] 3.68g curcumin (Fluka, high purity) and 2.10g 1,2,3,4-cyclopentane tetracarboxylic dianhydride were dissolved in 60mL of anhydrous dioxane, stirred at 60°C for 36h, and the reaction solution was cooled to At room temperature, 50 mL of ether was added, and the precipitate was collected by centrifugation. After the precipitate was washed with ether, it was vacuum-dried at room temperature to obtain 5.4 g of curcumin polycondensation product represented by formula (II), with a yield of 93%.

Embodiment 2

[0051] Embodiment 2: the synthesis of the toilet curcumin macromolecular polymer shown in formula (III)

[0052]The polycondensation product shown in 5.0g formula (II), 6.9g monomethoxypolyoxyethylene (Mn=800), 1.9g N, N-dicyclohexylcarbodiimide, 0.05g 4-dimethylaminopyridine Dissolve in 80mL of anhydrous DMSO, stir at room temperature for 18h, add 150mL of diethyl ether, centrifuge to collect the precipitate, dissolve the precipitate in tetrahydrofuran and then precipitate with diethyl ether to obtain a viscous solid and vacuum-dry it at room temperature to obtain 10.2g of formula (III ) shown high molecular polymer, yield 87%.

Embodiment 3

[0053] Embodiment 3: the synthesis of the selenium-containing curcumin polymer shown in formula (I)

[0054] Dissolve 6.8g of the polymer represented by formula (III) in 50mL of anhydrous tetrahydrofuran, add 5.5mg of N,N-dicyclohexylcarbodiimide, stir for 15min, then add 2.5mg of triethylamine, 4.5mg of methyl Selenocysteine, 3.0 mg 4-dimethylaminopyridine, stirred at room temperature for 12 hours, added 100 mL of ether, centrifuged to collect the precipitate, dissolved in tetrahydrofuran and added ether to precipitate, and vacuum dried at room temperature to obtain 6.5 g of formula 1 The shown selenium-containing curcumin high molecular polymer has a yield of 96%.

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Abstract

The invention discloses a selenium-containing curcumin polymer and its preparation method and application. The selenium-containing curcumin polymer has a structure as represented by formula (I). The polymer has the advantages of good stability, water-solubility and biocompatibility, low toxic and side effects, high bioavailability, easy injection and administration, obvious curative effects on inhibiting hepatic fibrosis, fatty liver and cirrhosis and a striking clinical application value.

Description

(1) Technical field [0001] The technical field of the invention is drug synthesis and application, and relates to a water-soluble selenium-containing curcumin polymer formed by combining curcumin derivatives with cyclopentanetetracarboxylic dianhydride, polyoxyethylene and methylselenocysteine Its preparation method and application as anti-hepatic fibrosis, anti-fatty liver and anti-cirrhosis drugs. (2) Technical background [0002] Curcumin is a polyphenolic compound extracted from the rhizomes of turmeric plants such as turmeric, turmeric, and zedoary, which has anti-inflammatory, anti-oxidation, anti-mutation, anti-aging, anti-tumor, and hypolipidemic properties . Curcumin has a wide range of sources, low price, and various curative effects. It is a food additive widely used in Southeast Asian countries (Mai Zhenjiang. Research progress in the pharmacological effects of curcumin. Chinese Materia Medica, 2004, (9): 698). Curcumin has the effect of anti-oxidative stress, ...

Claims

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Application Information

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IPC IPC(8): C08G63/91C08G81/00C08G65/329A61K31/80A61P1/16
Inventor 唐华东李小年
Owner 浙江益弹新材料科技有限公司
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