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Application of B/E ring substituted silybin for preparing medicament for treating virus 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 of not being effectively developed and few documents, and achieve large-scale production that is conducive to large-scale production, convenient source, energy saving and emission reduction Effect

Inactive Publication Date: 2010-12-22
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] 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 for anti-hepatitis B virus (including inhibition of HBsAg or HBeAg, inhibition of HBV DNA replication). Active compounds in the field of viruses, that is, structural modification of flavonoid lignans to have anti-DNA virus activity is a new field

Method used

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  • Application of B/E ring substituted silybin for preparing medicament for treating virus hepatitis B
  • Application of B/E ring substituted silybin for preparing medicament for treating virus hepatitis B
  • Application of B/E ring substituted silybin for preparing medicament for treating virus hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Compound (±)-2-[2,3-dihydro-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-hydroxymethyl-8-ethoxy- Preparation of 1,4-benzodioxane-6-]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0032] 1.1 Instruments and reagents:

[0033] 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 all 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...

Embodiment 2

[0046] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0047] 2.1 Cell culture:

[0048] 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.

[0049] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0050] 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

[0059] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0060] 3.1 Cell culture: the method is the same as in Example 2.

[0061] 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.

[0062] 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 100 μg / ml, 20 μg / ml and 4 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 a B / E ring substituted silybin for preparing a medicament for treating virus hepatitis B, in particular to the application of a B ring ethoxy and E ring methoxy substituted silybin ester or medicinal salts thereof for preparing the medicament for eliminating hepatitis B virus surface antigens and hepatitis B e antigen and inhibiting HBV and DNA replication. The medicament has accurate activity of inhibiting HBsAg and HbeAg, and respective intensity of 18.5% and 23.0% in eliminating HBsAg and HbeAg at the concentration of 100 microgram / ml, which exceeds the positive control medicament of an alpha-interferon; and meanwhile, 23.3% inhibition ratio on HBV and DNA is displayed at the concentration of 100 microgram / ml; and therefore, flavonoid lignans or a medicinal salt thereof are proved to have the efficacy of inhibiting HbsAg, HbeAg, HBV and DNA. The application is predictably used for preparing the non-nucleoside medicament for eliminating HBsAg and HbeAg, inhibiting HBV and DNA replication and treating hepatitis B virus infectious diseases.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, the present invention relates to a kind of silybin ester substituted by B ring ethoxy group and E ring methoxy group or its pharmaceutically acceptable salt is used for preparing and reducing hepatitis B virus surface antigen HBsAg and Use of hepatitis B e antigen HBeAg, inhibiting HBV DNA replication, and treating hepatitis B virus infection diseases. This flavonoid lignan has the definite activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 18.5% and 23.0% at 100 micrograms / ml concentration, all exceeds positive control drug (10000 units / ml alpha-interference At the same time, it showed a 23.3% inhibitory rate to HBV DNA at this concentration. The above shows that the flavonoid lignan or its pharmaceutically acceptable salt has the effect of inhibiting HBsAg, HBeAg and HBV DNA; it can be expected to be used to prepare non-nu...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20A61P1/16C07D407/04
Inventor 窦辉熊轶施贵荣汪峰张荣平巫秀美赵昱戴志明
Owner DALI UNIV
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