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Application of ring A coupling flavonolignan in preparing medicaments for treating viral hepatitis B

A flavonoid lignan and its application technology are applied in the field of drugs for the treatment of hepatitis B virus infection, which can solve the problems of insufficient literature and ineffective development, and achieve the effects of convenient source, convenient raw material source and clear industrialization prospect

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

[0016] 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 A coupling flavonolignan in preparing medicaments for treating viral hepatitis B
  • Application of ring A coupling flavonolignan in preparing medicaments for treating viral hepatitis B
  • Application of ring A coupling flavonolignan in preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Formula (1) (±)-trans-6-hydroxyl 2-hydroxymethyl-3-(3-bromo-4-hydroxyl-5-methoxyphenyl)-9-phenyl-2,3-dihydro- Preparation of [1,4]dioxane[2,3-h]benzopyran-7-one

[0034] Instruments and reagents:

[0035] 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 Biotech AB in Sweden; reverse-phase si...

Embodiment 2

[0041] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0042] 2.1 Cell culture:

[0043] 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.

[0044] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0045] 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

[0055] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0056] 3.1 Cell culture: the method is the same as in Example 2.

[0057] 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.

[0058] 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 culture med...

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Abstract

The invention relates to application of ring A coupling flavonolignan in preparing medicaments for treating viral hepatitis B, in particular to application of a compound of the formula (1) 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 intensities of the flavonolignan for clearing away the HBsAg and the HBeAg are respectively 29.4 percent and 29.1 percent in the presence of a concentration of 20 micrograms / milliliter, which is respectively 1.8 times and 1.7 times of the corresponding activity of a positive control medicament (10,000 units / milliliter of alpha-interferon). What is even more exciting is that in the presence of the concentration, the suppression rate of the flavonolignan to the HBV DNA is higher than 83 percent, which is higher than that of Lamivudine which is a positive control and is 2.2 times of that of the alpha-interferon to the HBV DNA. Accordingly, the flavonolignan and the pharmaceutically acceptable salt thereof are indicated to be capable of being expected to be used for preparing non-nucleoside medicaments for clearing away the HBsAg and the HBeAg, suppressing the HBV DNA replication and 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 A ring dioxane coupling type flavonoid lignan compound or its pharmaceutically acceptable salt is used for preparing and reducing hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, Use of the drug for inhibiting HBV DNA replication and treating hepatitis B virus infection diseases. This flavonoid lignan has significant activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 29.4% and 29.1% at a concentration of 20 micrograms / ml, which is positive control drug (10000 units / ml of α-interference 1.8 times and 1.7 times of the corresponding activity of α-interferon; what is even more exciting is that it shows an inhibition rate of greater than 83% to HBV DNA at this concentration, which is higher than that of the positive control lamivudine, and is an alpha-interferon ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20
Inventor 白丽张奇军王莹汪峰陈绍媛巫秀美赵昱谭仁祥
Owner DALI UNIV
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