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Application of ring E iodine substituted silybin in preparing medicaments for treating viral hepatitis B

A technology for silibinin and uses, which is applied in the field of medicine, can solve the problems of few literatures, has not been effectively developed, etc., and achieves the effects of convenient source, favorable for large-scale production, huge social benefit and economic benefit

Inactive Publication Date: 2012-02-01
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
The new application of flavonoid lignans in the treatment of DNA virus infection, especially its anti-hepatitis B virus (including inhibition of hepatitis B surface antigen HBsAg or HBeAg, inhibition of HBV DNA replication) has not been effectively developed

Method used

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  • Application of ring E iodine substituted silybin in preparing medicaments for treating viral hepatitis B
  • Application of ring E iodine substituted silybin in preparing medicaments for treating viral hepatitis B
  • Application of ring E iodine substituted silybin in preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Formula (1) compound (±)-2-[2,3-dihydro-3-(3-iodo-4-hydroxyl-5-methoxyphenyl)-2-hydroxymethyl-1,4-benzene Preparation of dioxane-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 all 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 s...

Embodiment 2

[0039] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0040] 2.1 Cell culture:

[0041] 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.

[0042] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0043] 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

[0052] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0053] 3.1 Cell culture: the method is the same as in Example 2.

[0054] 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.

[0055] 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 100 μg / ml, 20 μg / ml and 4 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 E iodine substituted silybin in preparing medicaments for treating viral hepatitis B, in particular to application of a compound of a formula (1) and a pharmaceutically acceptable salt thereof in preparing medicaments for clearing away hepatitis B surface antigens (HBsAg) and hepatitis e antigens (HBeAg) and suppressing the HBV (Hepatitis B Virus) DNA replication. The compound has definite activity of suppressing the HBsAg and the HBeAg, and in the presence of a concentration of 100 micrograms / milliliter, the intensities of the compound for clearing away the HBsAg and the HBeAg are respectively 20.0 percent and 29.0 percent which exceed that of a positive control medicament (10,000 units / milliliter of alpha-interferon) by 24 percent and 72 percent. Meanwhile, in the presence of the concentration, the suppression ratio of the compound on the HBV DNA is 32.6 percent which is close to that of the alpha-interferon. Accordingly, the flavone lignan or the pharmaceutically acceptable salt thereof are indicated to be capable of being 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 silybin ester substituted by E-ring iodine or a pharmaceutically acceptable salt thereof, which is used to prepare and reduce hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, and inhibit HBV DNA Application of drugs for replicating and treating hepatitis B virus infection. This flavonoid lignan has the definite activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 20.0% and 29.0% under the concentration of 100 micrograms / milliliter, surpasses positive contrast drug (10000 units / milliliter α-interference At the same time, it shows about 32.6% inhibitory rate to HBV DNA at this concentration, which is close to α-interferon. The above pharmacodynamic results show that the flavonoid lignan or its pharmaceutically acceptable salt can be expected to be used in the preparatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/357A61P31/20
Inventor 李辉郑群雄张桢杨雷香周长新巫秀美赵昱曾苏
Owner DALI UNIV
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