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Application of ring A substituted silybin ester in preparing medicaments for treating viral hepatitis B

A technology for the use of silibinin, which is applied in the field of the use of A ring to replace silibinin ester for the preparation of drugs for the treatment of viral hepatitis B, can solve the problems that the new use has not been effectively developed, and achieve the benefits of large-scale production, The effect of convenient source, huge social benefit and economic benefit

Inactive Publication Date: 2012-05-23
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] 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 HBsAg or inhibition of HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus is searched from flavonoid lignans, that is, the structural modification of flavonoid lignans Making it active against DNA viroids is a new field

Method used

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  • Application of ring A substituted silybin ester in preparing medicaments for treating viral hepatitis B
  • Application of ring A substituted silybin ester in preparing medicaments for treating viral hepatitis B
  • Application of ring A substituted silybin ester in preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Formula (1) compound (±)-2,3-dihydro-2-[2,3-dihydro-3-(4-hydroxyl-3-methoxyphenyl)-2-hydroxymethyl-1, Preparation of 4-benzodioxane-6-]-7-(ethoxyformylmethoxy)-3,5,-dihydroxy-4H-1-benzopyran-4-one

[0027] 1.1 Instruments and reagents:

[0028] 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 Pharmaci...

Embodiment 2

[0032] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0033] 2.1 Cell culture:

[0034] 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.

[0035] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0036] 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 i...

Embodiment 3

[0044] Example 3: Inhibition of the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by the compound of formula (1) to HepG2.2.15 cells

[0045] 3.1 Cell culture: the method is the same as in Example 2.

[0046] 3.2 The inhibitory effect of the flavonoid lignan compound represented by formula (1) on the growth of HepG2.2.15 cells was determined by MTT method: the method is the same as that in Example 2.

[0047] 3.3 The flavonoid lignan compounds shown in the assay formula (1) inhibit the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA): get the HepG2.2.15 cells in the logarithmic growth phase, and use the culture medium to dilute the cells to 1 ×10 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in an incubator with 100% relative humidity for 24 hours, add the flavonoid lignan compound shown in the formula (1) diluted with the medium, the concentration is respectively 100 microg...

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Abstract

The invention relates to application of ring A substituted silybin ester in preparing medicaments for treating viral hepatitis B, in particular to application of silybin ester flavonolignan substituted by ethoxycarbonyl methyl on the ring A or a pharmaceutically acceptable salt thereof for preparing medicaments for reducing the hepatitis B virus surface antigen (HBsAg), suppressing the HBV (Hepatitis B Virus) DNA replication and treating HBV infection diseases. The flavonolignan has quite obvious activity on suppressing the HBsAg, and in the presence of a concentration of 100 micrograms / milliliter, the intensity of the flavonolignan for clearing away the HBsAG exceeds that of alpha-interferon which is a positive control medicament by 3.3 times. Meanwhile, in the presence of a concentration of 20 micrograms / milliliter, suppression ratio of the compound to the HBV DNA is close to 60 percent. The pharmacodynamical results indicate that the flavonolignan or the pharmaceutically acceptable salt thereof can be expected to be used for preparing the medicaments for treating the HBV 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 silybin ester flavonoid lignan or its pharmaceutically acceptable salt which is substituted by ethoxyformyl methyl group on the A ring for the preparation of HBV surface-reducing Antigen HBsAg medicine, inhibition of HBV DNA replication, the purposes of medicine for treating hepatitis B virus infection disease, this flavonoid lignan has very significant activity of inhibiting HBsAg, and its clearing HBsAg intensity exceeds positive control medicine ( 10000 units / mL of α-interferon) 3.3 times; meanwhile, the compound showed an inhibition rate of nearly 60% on HBV DNA at a concentration of 20 μg / mL. The above pharmacodynamic results show that the flavonoid lignan or its pharmaceutically acceptable salt can be expected to be used in the preparation of drugs for reducing the surface antigen of hepatitis B virus, inhibiting HBV DNA repli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 周长新冯菊红申元英龚景旭潘远江巫秀美赵昱谭仁祥
Owner DALI UNIV
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