Preparation method of hinokiflavone derivative and application to melanoma resistance

A technology of cypress cypress biflavonoids and tert-butyldiphenyl cypress cypress bisflavonoids, which is applied in the field of medicine, can solve the problems of short circulation time in the body, low bioavailability, difficult cypress cypress biflavonoids, etc., and achieves easy operation and good selectivity. , the effect of low cost

Inactive Publication Date: 2018-07-20
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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  • Preparation method of hinokiflavone derivative and application to melanoma resistance
  • Preparation method of hinokiflavone derivative and application to melanoma resistance
  • Preparation method of hinokiflavone derivative and application to melanoma resistance

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The separation of embodiment 1 cypress biflavone

[0028] 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.

[0029] Cypress biflavone, yellow powder, easily soluble in DMSO. ESI-MSm / z: 537[M+H] - , mp 256~258℃, 1 HNMR (d-DMSO, 40...

Embodiment 2

[0030] Synthesis of Example 2 Cypress Biflavone Derivatives WG020

[0031] (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.

[0032]In addition to acetonitrile, the organic solvent used to dissolve cypress biflavone in the above-mentioned examples can al...

Embodiment 3

[0040] Example 3 Cypress biflavone derivative WG020 inhibits the proliferation of melanoma cells

[0041] 1. Experimental materials

[0042] 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.

[0043] Reagents Human-derived melanoma cells A375 and CHL-1, mouse-derived melanoma cells B16-F10, culture medium, trypsin, superior fetal bovine serum, tetramethylazo blue powder (MTT powder).

[0044] 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.

[0045] 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 certain number of c...

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Abstract

The invention belongs to the field of medicine, and provides a hinokiflavone derivative WG020, a preparation method of the hinokiflavone derivative and application to melanoma resistance. Through a cell toxicity experiment (MTT method), Hoechst33258 dyeing experiments, melanoma cell clone formation combination reaction experiments, flow cytometry (FCM) melanoma cell apoptosis experiments, westernblot (WB) apoptosis mechanism analysis experiments, cycle arrest experiments and tumor cell migration inhibition experiments, the results show that the WG020 has good inhibition effects on the clone formation of the melanoma cells; in addition, the melanoma cells can be induced to generate apoptosis; through data, the melanoma influence by the WG020 occurs in the period S of the cell period; goodinhibition effects are achieved on the melanoma cell migration. Therefore the hinokiflavone derivative WG020 can be used as a lead compound for inventing the novel anti-melanoma medicine. A novel source is provided for searching for the anti-melanoma medicine.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a cypress biflavone derivative, a preparation method thereof and an application in anti-melanoma 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 derived f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/352A61P35/00
Inventor 王刚李新民杨家强黎丹夏雯李晓飞
Owner ZUNYI MEDICAL UNIVERSITY
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