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Antiviral compound and its preparation method and application

An antiviral and compound technology, applied in the field of new compounds with antiviral activity and their preparation, can solve the problems of strong toxicity and side effects, expensive drugs, etc., and achieve strong antiviral activity, simple separation and purification, and good dose dependence Effect

Active Publication Date: 2019-07-23
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the U.S. Food and Drug Administration has approved more than 20 drugs for AIDS treatment, but these drugs are expensive and have strong toxic and side effects, which will induce the emergence of drug-resistant strains of the virus

Method used

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  • Antiviral compound and its preparation method and application
  • Antiviral compound and its preparation method and application
  • Antiviral compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The features and advantages of the present invention can be further understood through the following detailed description in conjunction with the accompanying drawings. The examples provided are only illustrative of the method of the present invention and do not limit the rest of the present disclosure in any way. [Example 1] Construction of enterocin biosynthetic gene cluster deletion mutant strain Δenc

[0041] Using the genomic DNA of wild-type 172205 as a template, primers enc-L1 (5'-CCTAGGCAGTTCCATCACCCCGTTCG-3', SEQ NO.1) and enc-L2 (5'-AAGCTTGTCGTCGCAGCAGCAGTTCG-3', SEQ NO.2) were designed for amplification To increase the upstream fragment enc-L of the enterocin synthetic gene cluster, design primers enc-R1 (5'-CATATGAGAGGGCGGACGGGAACTGC-3', SEQ NO.3) and enc-R2 (5'-CCTAGGGCGCCATCCCAACGGGCTAC-3', SEQ NO.4) for Amplify the downstream fragment enc-R of enterocin synthesis gene cluster. 20 μL PCR reaction system using Taq Mix enzyme: 8 μL Mix enzyme, 1 μL each pr...

Embodiment 2

[0045] [Example 2] Large-scale fermentation of the mutant strain 172205Δenc and its pretreatment method for fermented product samples

[0046] The mutant strain 172205Δenc obtained in Example 1 was inoculated in ISP2 liquid medium, cultured at 28°C and 200r / min for 3 days, and transferred to 12 shake flasks containing 100mL fermentation medium at 28°C with a 5% inoculum size. , 200r / min to continue culturing for 7 days to obtain a fermentation broth. The fermentation broth was directly extracted three times with an equal volume of ethyl acetate, during which ultrasonic waves and vibrations were performed several times, the ethyl acetate layers were combined, and concentrated to dryness under reduced pressure at 35°C to obtain a crude extract. The ISP2 liquid medium is composed of the following components: glucose 4g / L, yeast extract 4g / L, malt extract 10g / L, and the pH value is 7.2. The fermentation medium is composed of the following components: glucose 20g, soluble starch 1...

Embodiment 3

[0047] [Example 3] Isolation and structure confirmation of compounds

[0048] (1) Compound separation

[0049] About 1 g of the crude extract obtained in Example 2 was dissolved in an appropriate amount of methanol and then mixed into reverse silica gel, and the dry loading was carried out by reverse silica gel chromatography (methanol / water elution system) for elution and separation in sequence. The eluate of the target component was concentrated and then separated and purified using acetonitrile and water with a mobile phase ratio of 30:70 (volume ratio) using C18 semi-preparative liquid phase to obtain the target compound (4 mg).

[0050] (2) Planar structure confirmation

[0051] Via UV( image 3 ), IR ( Figure 4 ), MS( Figure 5 ) and NMR ( Figure 6-10 ) a variety of spectroscopic means to determine the structure of the above compound, its physical and chemical properties and spectral data are as follows:

[0052] Light brown powder; optical rotation: Molecular ...

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Abstract

The invention discloses a compound with antiviral activity and a preparation method and application of the compound. The compound has a structure shown in a formula (I) and can be prepared and obtained by fermentation and separation of a mutant strain with the deletion of the enterocin gene cluster of Streptomycete qinglanensis 1772205. A high-resolution mass spectrum and a nuclear magnetic resonance spectrum technology are adopted to confirm the structure of the compound. The compound with a structure shown as in the formula (I) has relatively strong antiviral activity and can be used for preparing medicines for treating viruses.

Description

technical field [0001] The invention belongs to the field of microbial medicines, in particular to a new compound with antiviral activity and its preparation method and application. Background technique [0002] Human immunodeficiency virus (human immunodeficiency virus, HIV), that is, AIDS virus, can cause defects in the human immune system. It was first discovered in the United States in 1981. According to the statistics of the World Health Organization, as of the end of 2014, there were about 36.9 million people living with HIV worldwide, about 2 million people were newly infected with HIV and 1.2 million people died of HIV-related causes in the same year. Due to the rapid mutation of the HIV virus, there is no effective cure so far, but some drugs have been developed that can inhibit the activity of the virus, slow down the course of the disease, and reduce the mortality and morbidity after infection. Due to the lag and insufficient popularization of AIDS education in m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/80C12P17/06A61K31/352A61P31/18C12R1/465
CPCC07D311/80C12P17/06
Inventor 洪葵徐东波田二丽庄柯刘航邓子新
Owner WUHAN UNIV
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