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Application of benzoyl silibinin for preparing medicaments for treating viral hepatitis B

A technology of silibinin and dimethoxybenzoyl, which is applied in the field of drugs for the treatment of hepatitis B virus infection, can solve the problems of no reported anti-HBV activity of flavonoid lignans, and facilitate large-scale production , Large-scale production of energy saving and emission reduction, and the effect of clear industrialization prospects

Inactive Publication Date: 2010-09-08
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Zuo Guoying et al. (Zuo Guoying, Liu Shuling, Xu Guili, World Chinese Journal of Digestion, 2006, Vol. 14, No. 13, pp. 1241-1246) reviewed the research progress of the anti-HBV activity of medicinal plant ingredients in vitro in the past 20 years. Natural products, there is no record of any flavonoid lignans having anti-HBV activity, especially silibinin natural products and their derivatives, almost no one in China, only the inventor team Previously unnoticed structural modification and antioxidant activity research

Method used

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  • Application of benzoyl silibinin for preparing medicaments for treating viral hepatitis B
  • Application of benzoyl silibinin for preparing medicaments for treating viral hepatitis B
  • Application of benzoyl silibinin for preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Formula (1) compound (±)-3,4-dimethoxybenzoic acid [3-(4-hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5, Preparation of 7-trihydroxy-4-oxo-1-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]methyl ester

[0030] 1.1 Instruments and reagents:

[0031] 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

[0035] Example 2: Inhibitory Effect of Compound of Formula (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0036] 2.1 Cell culture:

[0037] 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.

[0038] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth and HBsAg was measured by MTT method:

[0039] 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 of formula (1) diluted with medium, the concentration is respectively 1000 microgram / ml, 200 microgram / ml, 40 microgram / ml and 8 microgram / ml, every hole 200 microliters, three ...

Embodiment 3

[0048] Example 3: Inhibitory effect of compound of formula (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0049] 3.1 Cell culture: the method is the same as in Example 2.

[0050] 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.

[0051] 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 benzoyl silibinin for preparing medicaments for treating viral hepatitis B, in particular to application of 23-bit 3,4-dimethoxy-benzoyl substituted silibinin ester or medicinal salts thereof for preparing medicaments which are used for eliminating Hepatitis B virus surface antigen (HBsAg) and hepatitis B e antigen (HBeAg) and inhibiting HBV (Hepatitis B Virus) DNA replication. The compound plays an extremely remarkable role in inhibiting HBsAg and HBeAg activities, and the strengths for eliminating the HBsAg and the HBeAg under the concentration of 20 micrograms / ml in the compound are respectively 93.3 percent and 91.2 percent; meanwhile, the compound displays more than 99 percent of inhibition ratio to HBV DNA under the concentration of 20 micrograms / ml and has 23 percent of inhibition ratio higher than that of positive control medicine Lamivudine and 2.6 times higher than that of Alpha-interferon. Results indicate the application of flavone lignans and medicinal salts which are expectedly used for preparing non-nucleoside medicaments for eliminating the HBsAg and the HBeAg, inhibiting HBV DNA replication and treating hepatitis B virus infection diseases.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a 23-position 3,4-dimethoxybenzoyl substituted silybin ester or a pharmaceutically acceptable salt thereof for the preparation of HBV surface antigen-reducing Use of HBsAg and hepatitis B e antigen HBeAg, inhibiting HBV DNA replication, or 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 93.3% and 91.2% at a concentration of 20 micrograms / milliliter, respectively surpassing the positive control drug (10000 units / milliliter of α- Interferon) 5.8 times and 5.4 times; What's more exciting is: at this concentration, it shows an inhibition rate greater than 99% to HBV DNA, which is 23% higher than that of the positive control drug lamivudine, and higher than that of α-interferon Prime 2.6 times. The above pharmacody...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16C07D407/04
Inventor 姜北赵金浩周萍胡明辉陈柳蓉巫秀美赵昱戴志明
Owner DALI UNIV
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