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Selenium-containing curcumin polymer and its preparation method and application

A selenium-curcumin and polymer technology, applied in the field of water-soluble selenium-containing curcumin high molecular polymer and its preparation, can solve the problems of large amount of co-solvent used, complicated preparation process, high cost, etc., and achieve good stability Effect

Active Publication Date: 2013-12-04
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
Comparison scheme
Effect test

Embodiment 1

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

[0050] Dissolve 3.68g of curcumin (Fluka, high purity) and 2.10g of 1,2,3,4-cyclopentane tetracarboxylic dianhydride in 60mL of anhydrous dioxane, stir at 60°C for 36h, and then cool the reaction solution to At room temperature, 50 mL of ether was added, and the precipitate was collected by centrifugation. The precipitate was washed with ether and then 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 comb-shaped curcumin macromolecular polymer shown in formula (III)

[0052] Dissolve 5.0g of the polycondensation product represented by formula (II), 6.9g of monomethoxypolyoxyethylene (Mn=800), 1.9g of N,N-dicyclohexylcarbodiimide, and 0.05g of 4-dimethylaminopyridine In 80mL of anhydrous DMSO, stirred at room temperature for 18h, added 150mL of ether, centrifuged to collect the precipitate, dissolved in tetrahydrofuran and then precipitated with ether to obtain a viscous solid, dried in vacuum at room temperature, and obtained 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 of 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 Show selenium-containing curcumin high molecular polymer, yield 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 high molecular polymer formed by combining curcumin derivatives with cyclopentane tetracarboxylic 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-ox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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