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Application of dimethyl dehydrated silybin in preparing medicaments for treating virus hepatitis B

A dehydrogenated silibinin and application technology, applied in the field of medicine, can solve the problems that new applications 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: 2010-12-15
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] 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 sought from flavonolignans, also known as flavonoids Structural modification of lipids to have anti-DNA virus activity is a new field

Method used

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  • Application of dimethyl dehydrated silybin in preparing medicaments for treating virus hepatitis B
  • Application of dimethyl dehydrated silybin in preparing medicaments for treating virus hepatitis B
  • Application of dimethyl dehydrated silybin in preparing medicaments for treating virus hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Compound (±)-2-[2,3-dihydro-3-(3,4-dimethoxyphenyl)-2-hydroxymethyl-1,4-benzodioxane Preparation of -6-]-3,5-dihydroxy-7-methoxyl-4H-1-benzopyran-4-one

[0029] 1.1 Instruments and reagents:

[0030] 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 Chromator...

Embodiment 2

[0034] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0035] 2.1 Cell culture:

[0036] 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.

[0037] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0038] 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

[0047] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0048] 3.1 Cell culture: the method is the same as in Example 2.

[0049] 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.

[0050] 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 dimethyl dehydrated silybin in preparing medicaments for treating virus hepatitis B, in particular to the application of 7 and 20-position methyl substituted dehydrated silybin or pharmaceutically acceptable salts thereof in preparing medicaments for removing HBsAG and HBsAg and medicaments for inhibiting HBV DNA replication. The dehydrated silybin has remarkably HBsAg and HBeAg inhibiting activity, wherein the strength for removing the HBsAg and the HBeAg at the concentration of 20 milligram / milliliter is 88.9 percent and 84.1 percent respectively, which are 5.5 times and 5.0 times that of a positive contrast medicament. More importantly, the dehydrated silybin shows the HBV DNA inhibition ratio of about 99.6 percent at the concentration of 20 milligram / milliliter, the activity exceeds lamivudine by 23 percent, which is 2.6 times that of interferon. Therefore, favonolignan or pharmaceutically acceptable salts thereof can be predictably used for preparing the non-nucleoside reverse transcriptase inhibitor medicaments for removing the HBsAg and HBeAg, inhibiting HBV DNA replication and treating hepatitis B virus infection diseases.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a kind of dehydrosilibinin ester substituted by 7-position and 20-position methyl or its pharmaceutically acceptable salt is used for preparing and reducing hepatitis B virus surface antigen HBsAg and hepatitis B e Antigen HBeAg, inhibiting HBV DNA replication, or application of drugs for 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 88.9% and 84.1% at 20 micrograms / milliliter concentration, is positive control drug (10000 units / milliliter α-interference 5.5 times and 5.0 times that of lamivudine; more importantly: at this concentration, it shows about 99.6% inhibition rate to HBV DNA, and its activity exceeds that of lamivudine by 23%, which is 2.6 times that of interferon. The above pharmacodynamic results show t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20
Inventor 吴学东李湘萍陆丽冯玉冰李峰巫秀美赵昱钱金栿
Owner DALI UNIV
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