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

A technology of silibinin and its use, which is applied in the field of drugs for treating hepatitis B virus infection, can solve the problems that new uses have not yet been effectively developed, and achieve the effect of convenient, convenient and easy-to-obtain raw material sources

Inactive Publication Date: 2010-12-15
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: Formula (1) compound (±)-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] 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 t...

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, 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.

[0041] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0042] 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 24 hours in an incubator with 100% relative humidity, add compound (1) diluted with medium, the concentration is 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μg / ml in each well microliter, each concentration was set up in triplicate, placed at 37°C, 5% CO 2 , cultivated in an ...

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 Determination of the inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells by MTT method: the method is the same as in Example 2.

[0054] 3.3 Determination of the inhibitory effect of the compound on hepatitis B e antigen (HBeAg): take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1 × 10 with the medium 5 / ml, seeded in 96-well cell culture plate, 100ml per well, at 37°C, 5% CO 2 After culturing in an incubator with 100% relative humidity for 24 hours, add samples diluted with culture medium at concentrations of 20 μg / ml, 4 μg / ml and 0.8 μg / ml, 200 μl per well, and set three concentrations for each Multiple wells were placed at 37°C, 5% CO 2 , cultivated in an incubator with 100% relative humidity, change the culture med...

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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 and HBeAg; 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, in particular, the present invention relates to a kind of silybin ester whose E ring demethoxyl group or its pharmaceutically acceptable salt is used for the preparation of reducing hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, Use of the drug for inhibiting HBV DNA replication or treating hepatitis B virus infection. This flavonoid lignan has definite activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 95.0% and 34.4% at 20 micrograms / milliliter concentration, is positive control drug (10000 unit / milliliter α-interference It is 5.9 times and 2.0 times of the corresponding activity of lamivudine; it is very noteworthy that at this concentration, it shows an inhibition rate of about 91.5% to HBV DNA, which is 13% higher than that of lamivudine, which is the inhibitory activity of α-interferon 2.4 times. The above...

Claims

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Application Information

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Patent Type & Authority Applications(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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