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Application of p-bromo-cinnamyl silybin in preparing medicament for treating viral hepatitis B

A technology of silibinin and bromide, which is applied in the field of medicine, can solve problems such as not being effectively developed, and achieve the effects of convenient source of raw materials, less pollution, and convenient synthesis

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] Flavonoid lignans have not been effectively developed for the treatment of DNA-like virus infection, especially its use in anti-hepatitis B virus (including inhibiting hepatitis B surface antigen HBsAg or HBeAg, inhibiting HBV DNA replication), so from flavonoid lignans It is a new field to search for active compounds in the field of anti-HBV, that is, to modify the structure of flavonoid lignans so that they have anti-DNA virus activity

Method used

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  • Application of p-bromo-cinnamyl silybin in preparing medicament for treating viral hepatitis B
  • Application of p-bromo-cinnamyl silybin in preparing medicament for treating viral hepatitis B
  • Application of p-bromo-cinnamyl silybin in preparing medicament for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Formula (1) compound (±)-p-bromocinnamic acid [3-(4-hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxyl-4 Preparation of -oxy-1-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]methyl ester

[0028] 1.1 Instruments and reagents:

[0029] 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-ph...

Embodiment 2

[0033] Example 2: Inhibitory Effect of Compound of Formula (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0034] 2.1 Cell culture:

[0035] 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.

[0036] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0037] 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 , cultivat...

Embodiment 3

[0046] Example 3: Inhibitory effect of compound of formula (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0047] 3.1 Cell culture: the method is the same as in Example 2.

[0048] 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.

[0049] 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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PUM

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Abstract

The invention relates to application of p-bromo-cinnamyl silybin in preparing a medicament for treating viral hepatitis B, in particular to application of 23-site p-bromo-cinnamyl base substituted silybin ester or pharmaceutically acceptable salts thereof in preparing a medicament for removing surface antigen of a hepatitis B virus and a hepatitis B e antigen and inhibiting HBVDNA replication. The medicament has obvious HBsAg inhibiting and HBeAg inhibiting activity, and the strengths for removing HBsAg and HBeAg at the concentration of 20 microgrammes / ml are respectively 98.9 percent and 90.9 percent and respectively exceed the strength of a positive contrast medicament alpha-interferon by 6.1 times and 5.4 times; and meanwhile, the medicament displays about 60 percent of inhibition ratio on HBVDNA at the concentration and is 157 percent higher than the alpha-interferon. It is indicated that the favonolignan or the pharmaceutically acceptable salts thereof can be expected for preparing a non-nucleoside medicament for removing HBsAg and HBeAg, inhibiting HBVDNA replication and treating a hepatitis B virus infection disease.

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 bromocinnamoyl group at the 23rd position or its pharmaceutically acceptable salt, which is used to prepare HBsAg and HBeAg, Use of the drug for inhibiting HBV DNA replication or treating hepatitis B virus infection. This flavonoid lignan has extremely significant inhibition of HBsAg and HBeAg activity, and its intensity of removing HBsAg and HBeAg is respectively 98.9% and 90.9% under the concentration of 20 micrograms / milliliter, surpasses positive control drug (10000 units / milliliter α- interferon) 6.1 times and 5.4 times; more exciting is: at this concentration, it shows about 60% inhibition rate of HBV DNA, 157% higher than alpha-interferon. The above pharmacodynamic results show that the flavonoid lignan or its pharmaceutically acceptable salt can be expected to be used in the preparation of non-n...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20
Inventor 毛本勇潘云雪董光平龚景旭金一巫秀美赵昱钱金栿
Owner DALI UNIV
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