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Application of cinnamoyl silybin in preparing medicaments for treating viral hepatitis B

A technology based on silibinin and cinnamoyl, applied in the field of drugs for the treatment of hepatitis B virus infection, can solve the problems of not being effectively developed, and achieve the effects of convenient source of raw materials, large-scale production of energy saving and emission reduction, and low pollution

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

[0015] Flavonoid lignans have not been effectively developed for the treatment of DNA-like virus infection, especially its use in anti-hepatitis B virus (including inhibiting hepatitis B surface antigen HBsAg or HBeAg, inhibiting HBV DNA replication), so from flavonoid lignans It is a new field to search for active compounds in the field of anti-HBV, that is, to modify the structure of flavonoid lignans so that they have anti-DNA virus activity

Method used

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  • Application of cinnamoyl silybin in preparing medicaments for treating viral hepatitis B
  • Application of cinnamoyl silybin in preparing medicaments for treating viral hepatitis B
  • Application of cinnamoyl silybin in preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Formula (1) compound (±)-p-methylcinnamic acid [3-(4-hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxyl- Preparation of 4-oxo-1-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]methyl ester

[0028] 1.1 Instruments and reagents:

[0029] 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, and the boiling range of petroleum ether is 60 -90°C; thin-layer preparative chromatography (PTLC) uses aluminum foil silica gel plates from Merck; column chromatography uses dextran gel Sephadex LH-20 from Amersham Pharmacia B...

Embodiment 2

[0033] Example 2: Inhibitory Effect of Compound of Formula (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0034] 2.1 Cell culture:

[0035] 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.

[0036] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0037] 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 , cultiv...

Embodiment 3

[0046] Example 3: Inhibitory effect of compound of formula (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0047] 3.1 Cell culture: the method is the same as in Example 2.

[0048] 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.

[0049] 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 ...

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Abstract

The invention relates to application of cinnamoyl silybin in preparing medicaments for treating viral hepatitis B, in particular to application of 23-position 4-methyl cinnamoyl substituted silybin and pharmaceutically acceptable salts thereof in preparing medicaments for clearing hepatitis B surface antigen and hepatitis B e antigen, and medicaments for inhibiting the copying of HBV DNA. The 4-methyl cinnamoyl substituted silybin has obvious activity for inhibiting HBsAg and HBeAg, and has the force of clearing the HBsAg and HBeAg of 69.0 percent and 91.5 percent respectively at the concentration of 20 micrograms / milliliter, which exceed a positive control medicament alpha-interferon by 4.3 times and 5.4 times respectively. Meanwhile, the 4-methyl cinnamoyl substituted silybin shows the inhibition ratio of over 95 percent for HBV DNA. The favonolignan and the pharmaceutically acceptable salts thereof can be expected to prepare non-nucleoside medicaments for clearing the HBsAg and HBeAg, inhibiting the copying of the HBV DNA 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 23-position 4-methyl cinnamoyl substituted silybin ester or a pharmaceutically acceptable salt thereof for the preparation of lowered hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg , Inhibiting the replication of HBV DNA and treating hepatitis B virus infection diseases. This flavonoid lignan has extremely significant inhibition of HBsAg and HBeAg activity, and its intensity of removing HBsAg and HBeAg is respectively 69.0% and 91.5% under the concentration of 20 micrograms / milliliter, surpasses positive control drug (10000 unit / milliliter α- Interferon) 4.3 times and 5.4 times; What's more exciting is: at this concentration, it shows an inhibition rate greater than 95% to HBV DNA, which is 18% higher than that of the positive control drug lamivudine and higher than that of α-interference Prime 2.5 times. The abov...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20
Inventor 自俊青赵锋李海峰龚景旭周长新巫秀美赵昱谭仁祥
Owner DALI UNIV
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