Chrysin and amine cyclodextrin clathrate

A technology of cyclodextrin and chrysin, which is applied in the field of pharmaceuticals, can solve the problems of low intestinal absorption, poor water solubility and reduced activity of chrysin, achieve good pertinence, overcome low bioavailability, and improve stability

Inactive Publication Date: 2015-08-12
KUNMING UNIV OF SCI & TECH
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to the poor water solubility of chrysin and less intestinal absorption, the phenolic hydroxyl group at the 5,7-position in its molecular structure in vivo is easily metabolized by glycosylation, resulting in reduced activity (Tsuji, P. A. et al., Chem. Biol. Interact ., 2006, 164, 85)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Chrysin and amine cyclodextrin clathrate
  • Chrysin and amine cyclodextrin clathrate
  • Chrysin and amine cyclodextrin clathrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of inclusion compound of chrysin and mono-(6-ethylenediamino-6-deoxy)-β-cyclodextrin

[0028] (1) Preparation of single 6-OTs-β-CD

[0029] Take 210 g of β-cyclodextrin recrystallized with water, add it in batches to a three-necked bottle filled with 1300 mL of water, and stir at room temperature. Weigh 17.2 g of sodium hydroxide and dissolve it in 50 mL of water, then slowly add the aqueous solution of sodium hydroxide dropwise to the suspension of β-cyclodextrin until the reaction solution gradually becomes clear, and continue to stir for 1.5 h until the cyclodextrin in the reaction solution After the ethanol was completely dissolved and became clear, the acetonitrile (80 mL) solution containing 26.0 g p-toluenesulfonyl chloride was slowly added dropwise to the reaction solution (dropping was completed in about 30 minutes), and after stirring for 2 h, the insoluble matter was filtered off, and the filtrate was used Adjust the pH to 7.5 with 2 m...

Embodiment 2

[0035] Example 2: Preparation of inclusion compound of chrysin and mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin

[0036] (1) The preparation method of single 6-OTs-β-CD is the same as step (1) of Example 1;

[0037] (2) Preparation of mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin (DETA-β-CD)

[0038] Dissolve 3.0 g (2.3 mmol) of mono-6-OTs-β-CD in 20 mL of dry diethylenetriamine, stir at room temperature until completely dissolved, and react at 80°C for 10 h under nitrogen protection. After the reaction is completed, Slowly drop the reaction solution into 400 mL of acetone, stir at room temperature for 30 min, remove the filtrate by suction filtration, collect the white precipitate, dissolve the precipitate in a small amount of water, drop it into 300 mL of acetone again, stir for 0.5 h, and then suction filter The white precipitate was collected and dried in a vacuum oven. The obtained solid powder was ground and added to 200 mL of ethanol, and the white pre...

Embodiment 3

[0042] Example 3: Preparation of inclusion compound of chrysin and mono-(6-amino-6-deoxy)-β-cyclodextrin

[0043] (1) The preparation method of single 6-OTs-β-CD is the same as step (1) of Example 1;

[0044] (2) Single-6-N 3 -β - Preparation of CDs

[0045] Accurately weigh 10 g (8 mmol) of mono-6-OTs-β - CD was dissolved in 35 mL DMF, followed by the addition of 1.5 g NaN 3 Stir well, heat the reaction at 75°C for 12 h to complete the reaction of the raw materials, then slowly add the reaction solution dropwise into 400 mL of acetone and stir at room temperature, a white precipitate is formed, filter it with suction, dry the white solid for 24 h, and put it evenly into 400 mL of acetone, followed by ultrasonication for 10 min, and suction filtration to obtain pure mono-6-N 3 -β - CD, the yield is 90%; 1 H NMR (500 MHz, D 2 O, δ ppm): 5.77(s, 14H, 2, 3-OH of CD), 4.83-4.86(7H, 1-H of CD), 4.13-4.37(m, 6H, 6-OH of CD), 3.35 -3.85(m, 42H, 2, 3, 4, 5 and 6-H of CD...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a flavonoid chrysin and amine cyclodextrin clathrate, the amine cyclodextrin is amino-substituted beta-cyclodextrin, amine cyclodextrin and chrysin can generate clathration, ionic interaction of amine cyclodextrin and a phenolic hydroxyl group in amino and chrysin molecular structure is generated, chrysin water solubility of chrysin can be greatly increased, and a chrysin liquid preparation is conveniently formed. The clathrate has the advantages of water solubility, good stability and good external antineoplastic activity. The preparation method is simple, condition is mild, operation is easy, the method can be used for developing a novel chrysin preparation, and has important practical value.

Description

technical field [0001] The invention belongs to the technical field of pharmacy and relates to an inclusion compound of chrysin and amine cyclodextrin. Background technique [0002] The chemical name of chrysin (as shown in formula II) is 5,7-dihydroxyflavone, and the English name is chrysin. It is a natural flavonoid compound, which is widely derived from the seeds and stem bark of the bignoniaceae plant wood butterfly, pinaceae plants The heartwood of mountain white pine and the heartwood of mangospine, etc., are particularly high in propolis. [0003] [0004] Studies have shown that chrysin has a variety of important biological activities, such as anti-inflammatory, anti-oxidation, anti-virus, antihypertensive and hypoglycemic effects. Studies in recent years have shown that chrysin also has great development potential in the prevention and treatment of tumors, and has become the focus of research on the pharmacological activity of chrysin. Khoo et al (Khoo, B.Y...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/352
Inventor 廖霞俐高凯牛绕梅杨铜泽杨健杨波
Owner KUNMING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap