Application of E-ring demethoxy-silibinin for preparing medicament for treating viral hepatitis B

A technology for viral hepatitis and milk thistle, applied in the field of medicine, can solve the problems that new uses have not been effectively developed, and achieve the effects of convenient source of raw materials, large-scale production of energy saving and emission reduction, and convenient synthesis

Inactive Publication Date: 2012-10-10
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Although the flavonoid lignans represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on their antiviral treatment. The flavonoid lignans treat DNA virus infection especially Its new application for anti-hepatitis B virus (including inhibition of hepatitis B surface antigen HBsAg or HBeAg, inhibition of HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus is found from flavonoid lignans, that is, flavonoid lignans Structural modification of lipids to have anti-DNA virus activity is a new field

Method used

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  • Application of E-ring demethoxy-silibinin for preparing medicament for treating viral hepatitis B
  • Application of E-ring demethoxy-silibinin for preparing medicament for treating viral hepatitis B
  • Application of E-ring demethoxy-silibinin for preparing medicament for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: The compound of formula (1) (±)-2-[2,3-dihydro-3-(4-hydroxyphenyl)-2-hydroxymethyl-1,4-benzodioxane-6-]- Preparation of 2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0030] 1.1 Instruments and reagents:

[0031] UV spectrum was measured with Shimadzu UV-240 UV spectrophotometer; proton nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is the internal standard); ESI-MS is measured by BrukerEsquire 3000+ mass spectrometer, column chromatography uses silica gel (100-200, 200-300 and 300-400 mesh) and thin layer chromatography silica gel GF254 (10-40 mesh) are produced by Qingdao Ocean Chemical Plant; all reagents used are analytical pure, thin layer preparative chromatography (PTLC) ) Use Merck's aluminum foil silica gel plate; Sephadex LH-20 for column chromatography uses the product of Amersham Pharmacia Biotech AB in Sweden; reverse-pha...

Embodiment 2

[0038] Example 2: Inhibitory effect of compound (1) on hepatitis B surface antigen (HBsAg) secreted by HepG2.2.15 cells

[0039] 2.1 Cell culture:

[0040] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100U / ml penicillin and 100U / ml streptomycin, 100μg / ml G418, and placed at 37°C, 5% CO 2 , Cultivate in an incubator with 100% relative humidity.

[0041] 2.2 Determine the inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells by MTT method:

[0042] Take HepG2.2.15 cells in logarithmic growth phase and dilute the cells to 1×10 with medium 5 Pcs / ml, seeded on 96-well cell culture plate, 100 microliters per well, at 37℃, 5% CO 2 After culturing in a 100% relative humidity incubator for 24 hours, add the compound (1) diluted with the medium at the concentration of 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 per well Microliters, each concentration has three replicate wells, placed at 37℃, 5% CO 2 Cultivate in...

Embodiment 3

[0051] Example 3: Inhibitory effect of compound (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0052] 3.1 Cell culture: The method is the same as in Example 2.

[0053] 3.2 The MTT method was used to determine the inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells: the method was the same as in Example 2.

[0054] 3.3 Determine the inhibitory effect of the compound on hepatitis B e antigen (HBeAg): Take HepG2.2.15 cells in the logarithmic growth phase and dilute the cells to 1×10 with culture medium 5 / Ml, seeded in 96-well cell culture plate, 100ml per well, at 37℃, 5% CO 2 After culturing in a 100% relative humidity incubator for 24 hours, add samples diluted with culture medium at concentrations of 20 micrograms / ml, 4 micrograms / ml and 0.8 micrograms / ml, 200 microliters per well, and three for each concentration. Multiple holes, placed at 37℃, 5% CO 2 , Cultivate in a 100% relative humidity incubator, change the medium containi...

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Abstract

The invention relates to application of E-ring demethoxy-silibinin for preparing medicaments for treating viral hepatitis B, and particularly to application of compound in formula (1) and pharmaceutically acceptable salt thereof for preparing medicaments for clearing HBsAg and HBeAg and suppressing HBV DNA replication. The invention has extremely superactive activity for suppressing the HBsAg andHBeAg; in the presence of the concentration of 20 microgram per millilitre, the intensities for clearing the HBsAg and HBeAg are 95.0% and 34.4% respectively, which are 5.9 and 2.0 times corresponding activity of a positive control medicament alpha-interferon; and it should be noticed that the suppression ratio of the medicament for HBV DNA at the concentration is about 91.5%, which is 13% higher than lamivudine and 2.4 times alpha-interferon suppression activity. In summary, the flavonolignans or pharmaceutically acceptable salt thereof can be prospectively used for preparing non-nucleoside medicaments for clearing the HBsAg and HBeAg, suppressing HBV DNA replication and treating hepatitis B virus infection disease.

Description

Technical field [0001] The present invention relates to the technical field of medicine. Specifically, the present invention relates to an E-ring demethoxy-demethoxy silybin ester or a pharmaceutically acceptable salt thereof for preparing and reducing hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, Use of drugs for inhibiting HBV DNA replication or treating hepatitis B virus infection diseases. The flavone lignans have the exact inhibitory activity of HBsAg and HBeAg. At a concentration of 20 μg / ml, the HBsAg and HBeAg clearance are 95.0% and 34.4%, respectively. They are the positive control drugs (10,000 units / ml of α-interference). It is 5.9 times and 2.0 times of the corresponding activity; it is very noteworthy that: at this concentration, it shows about 91.5% inhibition rate of HBV DNA, which is 13% higher than lamivudine, which is α-interferon inhibitory activity 2.4 times. The above pharmacodynamic results show that the flavone lignan or its p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 彭芳王彩芳杨永寿冯玉冰岳建民巫秀美赵昱谭仁祥
Owner DALI UNIV
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