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Genistein derivative as well as preparation method and application thereof in pharmacy

A technology of genistein and derivatives, applied in the field of medicine, can solve the problem that the anti-tumor effect is not fully elucidated, and achieve the effect of good inhibition of tumor cell invasion and migration, and good therapeutic effect.

Active Publication Date: 2016-07-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, genistein has a wide range of pharmacological effects, and the mechanism of its anti-tumor effect has not yet been fully elucidated.

Method used

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  • Genistein derivative as well as preparation method and application thereof in pharmacy
  • Genistein derivative as well as preparation method and application thereof in pharmacy
  • Genistein derivative as well as preparation method and application thereof in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation method of genistein derivatives: genistein 2.7g (10.0mmol), dehydrated alcohol 150mL, heat to dissolve, add potassium carbonate 1.5g (11.0mmol), potassium iodide catalytic amount, epichlorohydrin 9.3g ( 0.10mol), refluxed for 10h, filtered while it was hot, cooled, precipitated crystals, and filtered with suction to obtain 1.64g of a light yellow solid with a yield of 42.9%, which was 7,4'-bis(2,3-epoxypropoxy) -5-Hydroxyisoflavone, 7,4'-bis(2,3-epoxypropoxy)-5-hydroxyisoflavone is directly put into the next step reaction; 7,4'-bis(2,3-epoxypropyl Oxygen)-5-hydroxyisoflavone 500mg (1.3mmol), absolute ethanol 30mL, heat to dissolve, add piperidine 340mg (4.0mmol), reflux for 5h, product column chromatography (chloroform:methanol=100:3), 135 mg of pale white solid (compound GEN-27) was obtained, with a yield of 18.7%.

[0048] Physicochemical properties of compound GEN-27: M.p.140~143℃; ESI-MSm / z:553[M+H] + , suggesting a molecular weight of 552 and a mo...

Embodiment 2

[0052] 1. Experimental materials

[0053] (1) Drugs

[0054] Genistein derivatives (GEN-27), purity>99.5%; genistein (GEN), purity>99.5%.

[0055] GEN-27 and GEN were made into 100mM stock solutions with DMSO, stored at -20°C, and sample solutions with required concentrations were made with RPMI-1640 medium containing 10% fetal bovine serum before use.

[0056] (2) cell line

[0057] Human colon cancer HCT116 cell line, HT29 cell line, SW620 cell line, human normal colonic mucosal epithelial cell FHC cell line were from the cell bank of the Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, with 10% fetal bovine serum Cultured in RPMI-1640 medium (the same below).

[0058] (3) Reagents

[0059] 1) RPMI-1640 medium: Dissolve 10.4 g of RPMI-1640 powder (product of GIBCO, USA) in 1000 mL of sterilized three-distilled water, and use NaHCO 3 Adjust the pH value to 7.3-7.4, filter and sterilize with a cylindrica...

Embodiment 3

[0082] To investigate the preventive effect of compound GEN-27 on the azoxymethane (AOM) / dextran sodium sulfate (dextransodiumsulfate, DSS)-induced ulcerative colitis-associated colorectal cancer model in mice.

[0083] Administration method: the test compound was mixed into the mouse food according to the corresponding dose concentration, and administered by feeding method.

[0084]Establishment of AOM / DSS mouse colorectal cancer model: C57BL / 6 mice (purchased from Nanjing Institute of Biomedicine, Nanjing University), 70 healthy, vigorous male mice weighing 18-20 g were randomly divided into 7 Group, 10 in each group. Seven days after the mice adapted to a normal diet, it was recorded as the start day of the experiment, and the normal diet was replaced with a diet containing the corresponding concentration of the compound. On the 14th day after the start of the experiment, each mouse was intraperitoneally injected (i.p.) 10.0 mg / kg of azoxymethane, and after 7 days, it was ...

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Abstract

The invention belongs to the field of medical technology and discloses a genistein derivative with a structure shown by formula I in the specification or a pharmaceutically acceptable salt thereof. The invention also discloses an application of the genistein derivative or the pharmaceutically acceptable salt thereof in preparing a tumor treating medicine, an application in preparing an inflammation-related tumor treating medicine and an application in preparing a medicine inhibiting tumor cell invasion and migration. The genistein derivative disclosed by the invention generates a growth inhibiting and killing effect on tumor cells to realize an anti-tumor effect and has broad-spectrum anti-tumor activity while the effect is relatively good; the genistein derivative promises a perfect treatment effect on the AOM / DSS induced inflammation related tumor; and with relatively good ability of inhibiting tumor cell invasion and migration, the genistein derivative can be used for preparing a medicine inhibiting tumor migration and can be made into tumor migration inhibiting medicines of various dosage forms, thereby providing a better choice for tumor patients.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to genistein derivatives and their preparation methods and applications in pharmacy, in particular to the application of genistein derivatives or pharmaceutically acceptable salts thereof in the preparation of antitumor drugs . Background technique [0002] Anti-tumor drugs play an anti-tumor role through different mechanisms. For example, some literature divides chemotherapy drugs into alkylating agents, anti-metabolites, anti-cancer antibiotics, herbal medicines, and hormones according to the traditional classification. According to the mechanism of action, it can also be divided into drugs that directly damage DNA, drugs that insert DNA templates, drugs that interfere with nucleic acid synthesis, drugs that inhibit microtubule assembly, drugs that affect protein synthesis, and drugs with other mechanisms of action. Understanding the mechanism of action of antitumor drugs is more ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/453A61P35/00A61P35/02A61P35/04
CPCC07D311/36
Inventor 胡容芦金荣王亚菁耿晓婷杜前明唐静静陶磊卢平费怀君
Owner CHINA PHARM UNIV
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