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A preparation method of cypress biflavone derivatives and its anti-breast cancer application

A kind of cypress biflavonoids, anti-breast cancer technology

Active Publication Date: 2019-12-24
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the disadvantages of insoluble in water, low in vitro activity, short circulation time in vivo, high oral dose and low bioavailability of cypress biflavone, its clinical application is limited.

Method used

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  • A preparation method of cypress biflavone derivatives and its anti-breast cancer application
  • A preparation method of cypress biflavone derivatives and its anti-breast cancer application
  • A preparation method of cypress biflavone derivatives and its anti-breast cancer application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The separation of embodiment 1 cypress biflavone

[0026] Industrialized countercurrent chromatography (UK Dynamic Extract company) was applied to the separation and purification of cypress biflavonoids from the crude extract of Selaginella chinensis, and the solvent system consisted of 8:8:9:7 n-pentane-ethyl acetate-methanol-water Two-phase system, according to this ratio, the two-phase solvent system is injected into the column through different pumps at a rate of 600mL / min. Obtained cypress biflavone monomer 10g, the whole separation time is only 30min, for the first time broke through the technical difficulties of long separation time and low separation efficiency of countercurrent chromatography technology, and realized the rapid and large-scale preparation of high economic value monomer compound technology by countercurrent chromatography.

[0027] Cypress biflavone, yellow powder, easily soluble in DMSO. ESI-MSm / z: 537[M+H] - , mp 256~258℃, 1 HNMR (d-DMSO, 40...

Embodiment 2

[0028] Synthesis of Example 2 Cypress Biflavone Derivatives WG020

[0029] (1) Accurately weigh 10g of cypress biflavonoids, add 50ml of dry acetonitrile to dissolve, add 2ml of imidazole after complete dissolution, add 5.5g of TBSCl dropwise at room temperature, and react at room temperature for 1h after the dropwise addition. After the reaction was completed, add 100ml of dichloromethane and 100ml of water, separate layers, extract the aqueous layer with dichloromethane 3 times (50ml once), combine the extracts, wash with 100ml of water, wash with 100ml of saturated brine, and wash the organic layer with anhydrous sodium sulfate After drying and concentration, it was subjected to silica gel column chromatography (chloroform: acetone = 10:1) to obtain 7.8 g of yellow solid product tert-butyldiphenylcypress biflavone, which was dried for later use.

[0030] In addition to acetonitrile, the organic solvent used to dissolve cypress biflavone in the above-mentioned examples can a...

Embodiment 3

[0038] Example 3 Cypress biflavone derivative WG020 inhibits the proliferation of breast cancer cells

[0039] 1. Experimental materials

[0040] Test drug Cypress biflavone derivative WG020, light yellow powder, 98% purity, dissolved in DMSO, filtered and sterilized for storage, diluted with cell culture medium before use.

[0041] Reagents Human-derived breast cancer cells MDA-MB-231 and MCF-7, mouse-derived breast cancer cells 4T1, culture medium, trypsin, superior fetal bovine serum, tetramethyl azo blue powder (MTT powder ).

[0042] 2. Experimental equipment micro-adjustable pipette, cell counter, CO 2 Incubator, Millipore water purifier, low-temperature centrifuge, enzyme label detector, -80 ℃ ultra-low temperature refrigerator, constant temperature mixer, inverted microscope.

[0043] 3. Experimental process When the growth activity of the cells tends to be stable, spread the above three types of cells evenly in a 96-well plate, and add 100 μL of medium containing a...

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Abstract

The invention belongs to the technical field of medicine, and relates to a preparation method of hinokiflavone derivatives WG020 and application of the hinokiflavone derivatives WG020 in resistance tobreast cancer. Hinokiflavone is an extract from dark green selaginella in selaginella plants, and the hinokiflavone derivatives WG020 are synthesized on the basis of the extracted hinokiflavone. According to the preparation method, a cytotoxicity experiment (an MTT method), a flow cytometer (FCM) breast cancer cell apoptosis experiment, a western blotting (WB) analysis apoptosis mechanism experiment and a tumor cell metastasis inhibition experiment are performed on the WG020, and the result shows that influence of the WG020 on the activity of breast cancer cells is time-dependent and concentration-dependent, and the WG020 can induce the apoptosis of the breast cancer cells and has a better inhibitory effect on the metastasis of the breast cancer cells. Therefore, the hinokiflavone derivatives WG020 can be used as newly developed anti-breast cancer lead compounds, and provide a new source for seeking anti-breast cancer drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to the preparation of WG020, a biflavone derivative of cypress, and its application in anti-breast cancer drugs. Background technique [0002] At present, finding anti-tumor drugs from natural products or their derivatives is still the main way for humans to obtain anti-tumor drugs. According to reports by Demain et al., between 1981 and 2002, 74% of antineoplastic drugs were derived from natural products, semi-synthetics or total synthetics modeled on natural products. Paclitaxel, hydroxycamptothecin, colchicine, oxaliplatin, vincristine, and vindesine are all first-line anticancer drugs extracted from plants. Therefore, it is of great significance to find novel anticancer compounds with high efficiency, strong specificity, non-toxicity or low toxicity from natural plants, or use them as lead compounds to create new anticancer drugs. [0003] Cypress biflavonoids, wh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/7048A61P35/00C07H5/06C07H1/00
CPCA61K31/7048A61P35/00C07H1/00C07H5/06
Inventor 王刚李新民杨家强蒋永梅罗秦美李晓飞
Owner ZUNYI MEDICAL UNIVERSITY
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