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Application of ring B ethyoxyl silybin in preparing medicaments for treating viral hepatitis B

A technology of silibinin and ethoxylate, which is applied in the field of medicine, can solve the problems of less literature and no effective development, and achieve the effect of convenient source, convenient source of raw materials, and simple and easy preparation method

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] Although the flavonoid lignan compounds represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on their antiviral treatment
Flavonoid lignans have not been effectively developed for the treatment of DNA-like virus infection, especially for anti-hepatitis B virus (including inhibition of HBsAg or HBeAg, inhibition of HBV DNA replication). Active compounds in the field of viruses, that is, structural modification of flavonoid lignans to have anti-DNA virus activity is a new field

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Compound of formula (1) (±)-2-[2,3-dihydro-3-(3-methoxy-4-hydroxyphenyl)-2-hydroxymethyl-8-ethoxy-1,4 Preparation of -benzodioxane-6-]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[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 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 sil...

Embodiment 2

[0044] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0045] 2.1 Cell culture:

[0046] 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.

[0047] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0048] 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

[0057] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0058] 3.1 Cell culture: the method is the same as in Example 2.

[0059] 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.

[0060] 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, the concentrations are 20, 4 and 0.8 micrograms / ml, 200 microliters per well, and three duplicate holes are set for each concentration, and placed in 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 ring B ethyoxyl silybin in preparing medicaments for treating viral hepatitis B, in particular to application of ring B ethyoxyl substituted silybin ester or a pharmaceutically acceptable salt thereof in preparing medicaments for clearing away HBsAG (Hepatitis B Surface Antigen) and HBeAg (Hepatitis B e Antigen) and suppressing the HBV (Hepatitis B Virus) DNA replication. The compound has strong activity on suppressing the HBsAG and the HBeAg, and in the presence of a concentration of 20 micrograms / milliliter, the intensities for clearing the HBsAg and the HBeAg are respectively 64.6 percent and 44.8 percent which are 4.0 times and 2.7 times of that of alpha-interferon which is a positive control medicament. In the presence of the concentration, the suppression rate of the compound on the HBV DNA is 58.1 percent which is 1.5 times of the corresponding activity of the alpha-interferon. Accordingly, the flavonolignan or the pharmaceutically acceptable salt thereof are indicated to simultaneously have strong efficacy on suppressing the HBsAg, the HBeAg and the HBV DNA and can be expected to be used for preparing non-nucleoside medicaments for treating 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 substituted by B ring ethoxy group or its pharmaceutically acceptable salt, which is used to prepare and reduce hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, inhibit Application of HBV DNA replication and medicine for treating hepatitis B virus infection. The flavonoid lignans have a potent activity of inhibiting HBsAg and HBeAg, and at a concentration of 20 micrograms / ml, the intensity of removing HBsAg and HBeAg is 64.6% and 44.8%, respectively, which are positive control drugs (10000 units / ml of α- 4.0 times and 2.7 times that of α-interferon); at this concentration, it shows an inhibition rate of 58.1% to HBV DNA, which is 1.5 times that of α-interferon. The above shows that the flavonoid lignan or its pharmaceutically acceptable salt has the effect of inhibiting HBsAg, HBeAg and HBV DNA...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 郭宪国肖业成焦春香李海波于荣敏巫秀美赵昱钱金栿
Owner DALI UNIV
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