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Application of dehydrogenation silybin in preparation of medicament for treating virus hepatitis B

A technology for dehydrosilibinin and viral hepatitis, which is applied in the field of medical technology, can solve the problems of less literature and no effective development, and achieve the effect of convenient source, convenient source of raw materials, and simple and easy preparation method

Inactive Publication Date: 2010-09-15
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although the flavonoid lignan compounds represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on their antiviral treatment
Flavonoid lignans have not been effectively developed for the treatment of DNA-like virus infection, especially their new application in anti-hepatitis B virus (especially inhibiting HBV DNA replication). Compounds, that is, structural modification of flavonoid lignans to have anti-DNA viroid activity is a new field

Method used

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  • Application of dehydrogenation silybin in preparation of medicament for treating virus hepatitis B
  • Application of dehydrogenation silybin in preparation of medicament for treating virus hepatitis B
  • Application of dehydrogenation silybin in preparation of medicament for treating virus hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of Formula (1) Compound Dehydrosilibinin by Total Synthesis

[0026] 1.1 Instruments and reagents:

[0027] The ultraviolet spectrum was measured with a Shimadzu UV-240 ultraviolet spectrophotometer; the hydrogen nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA type superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is the internal standard); (100-200, 200-300 and 300-400 mesh) and silica gel GF254 (10-40 mesh) for thin-layer chromatography are produced by Qingdao Ocean Chemical Factory; all reagents used are analytically pure, thin-layer preparative chromatography (PTLC ) uses the aluminum foil silica gel plate of Merck Company; Sephadex LH-20 used for column chromatography adopts the product of Amersham Pharmacia Biotech AB Company of Sweden; Reversed-phase silica gel RP-18 adopts the Chromatorex product of Fuji Silysia Chemical Company of Japan; MCI is the product of Mitsu...

Embodiment 2

[0040] Example 2: Compound (±)-2-[2,3-dihydro-3-(4-hydroxyl-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxane Preparation of cyclo-6-]-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0041] 2.1 Instruments and reagents: Same as Example 1.

[0042]2.2 Preparation method 2 of compound (1):

[0043] Dissolve 1.0 g of commercially available silibinin (Liaoning Panjin Pharmaceutical Company) in 10 ml of DMF solvent, add 0.5 g of potassium carbonate, stir at 50°C for 12 hours, pour the reactant into 30 ml of water, and precipitate a yellow precipitate. Extract with ethyl acetate, dry over anhydrous sodium sulfate, filter, and concentrate the mother liquor under reduced pressure to obtain a yellow solid, which is eluted by 200-300 mesh silica gel column chromatography with chloroform-methanol (10:1) to finally obtain compound (1). Hydrogen silybin 0.65g. R f Value (chloroform: ethyl acetate: oxalic acid=25:1:0.25): 0.17; H NMR spectrum and electrospray mass spectrometry data are the s...

Embodiment 3

[0044] Example 3: Inhibition of the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by the compound of formula (1) to HepG2.2.15 cells

[0045] 3.1 Cell culture:

[0046] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100 U / ml penicillin and 100 U / ml streptomycin, 100 μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity.

[0047] 3.2 The inhibitory effect of compound (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0048] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in the incubator of 100% relative humidity for 24 hours, add the compound (1) diluted with medium, the concentration is respectively 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μg / ml in each hole microliter, each concentration wa...

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Abstract

The invention relates to application of dehydrogenation silybin in preparation of a medicament for treating virus hepatitis B, in particular to application of the dehydrogenation silybin or pharmaceutically acceptable salt thereof in preparation of the medicament for inhibiting HBV DNA replication. The medicament has obvious high hepatitis B virus desoxyribonucleic acid (HBV DNA) inhibiting activities and shows over 55 percent of inhibition rate for the HBV DAN at the concentration of 20 mg / ml, which is 1.5 times higher than that of a positive control medicament (10,000 unit / ml of alpha-interferon). The pharmacodynamics result shows the flavonolignan or the pharmaceutically acceptable salt thereof can be expected for preparing the non-nucleoside medicament for inhibiting HBV DNA replication and curing diseases caused by infection of hepatitis B virus.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to the use of dehydrosilibinin or a pharmaceutically acceptable salt thereof for the preparation of medicines for inhibiting HBV DNA replication, which has significant hepatitis B virus deoxyribonucleic acid HBV DNA Inhibitory activity, at a concentration of 20 μg / ml, it exhibits an inhibitory rate of greater than 55% on HBV DNA, which is 1.5 times higher than that of the positive control drug (α-interferon at 10,000 units / ml). The above pharmacodynamic results show that the flavonoid lignan or its pharmaceutically acceptable salt can be expected to be used in the preparation of non-nucleoside drugs for inhibiting HBV DNA replication or treating hepatitis B virus infection. Background technique [0002] Hepatitis B (HBV) is an infectious disease caused by the hepatitis B virus, HBV. HBV is a member of the hepadnaviridae family of hepadnavirid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 魏尔清胡利红刘晓波冯玉冰廖晓辉巫秀美赵昱钱金栿
Owner DALI UNIV
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