Application of substituted silybin ester in preparing medicament for treating virus hepatitis B

A technology for silibinin and uses, which is applied in the field of use of replacing silibinin ester for preparing a drug for the treatment of viral hepatitis B, and achieves the effects of convenient synthesis, easy-to-obtain raw material sources, and favorable energy saving and emission reduction.

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

[0014] Flavonoid lignans have not been effectively developed for the treatment of DNA-like virus infection, especially for anti-hepatitis B virus (including inhibiting hepatitis B surface antigen HBsAg or inhibiting HBV DNA replication). The active compounds in the field of hepatitis B virus, that is, the structural modification of flavonoid lignans so that they have anti-DNA virus activity is a new field

Method used

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  • Application of substituted silybin ester in preparing medicament for treating virus hepatitis B
  • Application of substituted silybin ester in preparing medicament for treating virus hepatitis B
  • Application of substituted silybin ester in preparing medicament for treating virus hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Formula (1) compound (±)-malonic acid [3-(4-hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxyl-4- Preparation of oxo-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]-methylethyl ester

[0026] 1.1 Instruments and reagents:

[0027] 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 Biotec...

Embodiment 2

[0031] Example 2: Inhibitory Effect of Compound of Formula (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0032] 2.1 Cell culture:

[0033] 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.

[0034] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0035] 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 cultivating in the incubator of 100% relative humidity for 24 hours, add the compound (1) diluted with medium, the concentration is respectively 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μg / ml in each hole microliter, each concentration was set up in triplicate, p...

Embodiment 3

[0043] 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

[0044] 3.1 Cell culture: the method is the same as in Example 2.

[0045] 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.

[0046] 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 culture medium, the concentration is respectively 10...

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Abstract

The invention relates to application of substituted silybin ester in preparing a medicament for treating virus hepatitis B, in particular to application of 23-position ethyl-malonyl substituted silybin ester or medicinal salt thereof in preparing a medicament for reducing hepatitis B virus surface antigen HBsAg, inhibiting HBV DNA replication and treating hepatitis B virus infected diseases. The flavonolignan has remarkable effect of inhibiting HBsAg activity, and the strength of the flavonolignan at the concentration of 100 micrograms per milliliter for clearing the HBsAg is two times and half that of a positive control medicament alpha-interferon; and meanwhile, the compound has strong inhibiting activity on the HBV DNA. Pharmacodynamical results show that the flavonolignan or the medicinal salt thereof can be expected to be used for preparing the medicament for reducing hepatitis B virus surface antigen, inhibiting HBV DNA replication and treating the hepatitis B virus infected diseases.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a silybin ester substituted with 23-position ethylmalonyl or a pharmaceutically acceptable salt thereof, which is used for preparing medicines for reducing hepatitis B virus surface antigen HBsAg and inhibiting HBV DNA The purposes of the medicine of replicating or treating hepatitis B virus infection disease, this flavonoid lignan has very significant activity of suppressing HBsAg, and its intensity of removing HBsAg exceeds positive control medicine (10000 units / ml of α - interferon) 2 and a half times; meanwhile, the compound showed an inhibition rate greater than 84% to HBV DNA at a concentration of 100 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 medicines for reducing hepatitis B virus surface antigen, inhibiting HBV DNA replication, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20
Inventor 彭芳陈海永杨月娥胡明辉于荣敏巫秀美赵昱郝小江
Owner DALI UNIV
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