CN104958755B - Application of the teicoplanin in anti-Middle East respiration syndrome coronavirus pharmaceutical is prepared - Google Patents
Application of the teicoplanin in anti-Middle East respiration syndrome coronavirus pharmaceutical is prepared Download PDFInfo
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- 208000011580 syndromic disease Diseases 0.000 title claims abstract description 29
- 230000029058 respiratory gaseous exchange Effects 0.000 title claims abstract description 28
- 241000711573 Coronaviridae Species 0.000 title claims abstract description 26
- 108010053950 Teicoplanin Proteins 0.000 title claims description 29
- 229960001608 teicoplanin Drugs 0.000 title claims description 29
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 title claims description 28
- -1 teicoplanin class compound Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229940096437 Protein S Drugs 0.000 claims description 7
- 108700002856 Coronavirus Envelope Proteins Proteins 0.000 claims description 2
- 241000127282 Middle East respiratory syndrome-related coronavirus Species 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 6
- 238000000338 in vitro Methods 0.000 abstract 1
- 241000315672 SARS coronavirus Species 0.000 description 12
- 239000005089 Luciferase Substances 0.000 description 10
- 239000006228 supernatant Substances 0.000 description 10
- 101710091045 Envelope protein Proteins 0.000 description 8
- 102100034349 Integrase Human genes 0.000 description 8
- 208000025370 Middle East respiratory syndrome Diseases 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 6
- 230000001629 suppression Effects 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 101000629313 Severe acute respiratory syndrome coronavirus Spike glycoprotein Proteins 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 208000037797 influenza A Diseases 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 229920000209 Hexadimethrine bromide Polymers 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
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- 239000000203 mixture Substances 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 238000001890 transfection Methods 0.000 description 3
- 208000001528 Coronaviridae Infections Diseases 0.000 description 2
- 241000711975 Vesicular stomatitis virus Species 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000011543 agarose gel Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 241000187844 Actinoplanes Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MQUQNUAYKLCRME-INIZCTEOSA-N N-tosyl-L-phenylalanyl chloromethyl ketone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@H](C(=O)CCl)CC1=CC=CC=C1 MQUQNUAYKLCRME-INIZCTEOSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 241001520299 Phascolarctos cinereus Species 0.000 description 1
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 1
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- 239000012930 cell culture fluid Substances 0.000 description 1
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- 229940055695 pancreatin Drugs 0.000 description 1
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- 229960005486 vaccine Drugs 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 206010048282 zoonosis Diseases 0.000 description 1
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
A kind of teicoplanin class compound is preparing anti-Middle East respiration syndrome coronavirus（MERS‑CoV）Application in medicine, present invention discover that teicoplanin class compound can effectively treat Middle East respiration syndrome coronavirus in vitro（MERS‑CoV）.
Description
Technical field
The present invention relates to the new opplication of antiviral drugs, is being prepared more particularly, to a kind of teicoplanin class compound
Anti- Middle East respiration syndrome coronavirus（MERS-CoV）And severe acute respiratory syndrome coronavirus（SARS-CoV）Medicine
Application in thing.
Background technology
Middle East respiration syndrome, is a kind of acute respiratory disease as caused by novel coronavirus found for 2012,
The infection of this novel coronavirus is named as " Middle East respiration syndrome " by May 23rd, 2013, the World Health Organization.The disease
Poison is appeared for the first time in Saudi Arabia, is then spread in the area such as Middle East other countries and Europe, and reporting the first in South Korea at the beginning of 2015 makes a definite diagnosis
Case, and cause and be propagated further.May 29, circulates a notice of, Guangdong Province Huizhou according to China's national health and Family Planning Committee
There are the first Introduced cases Middle East respiration syndrome confirmed cases in city.
Middle East respiration syndrome coronavirus is the Zoonosis virus that people is transmitted to from animal, then the viral origin
It is not fully understood.Current reported cases are counted and are found, which is about 36%.However, the current world
On still lack the vaccine and medicine of effective anti-Middle East respiration syndrome coronavirus.It is coronal currently for Middle East respiration syndrome
Virus, market do not have ready-made antiviral drugs to use.
Teicoplanin, also known as Teicoplanin Targocin, are found for 1975 first.It is specific actinoplanes, fermented, carry
A kind of vancomycin race glycopeptide antibiotics obtained after taking, are the antibiosis of the closely similar compound composition of multiple chemical constitutions
Plain mixture.
The content of the invention
The present invention provides a kind of pharmaceutical Teicoplanin new application, and a kind of teicoplanin class compound is exhaled preparing the anti-Middle East
Inhale syndrome coronavirus（MERS-CoV）And severe acute respiratory syndrome coronavirus（SARS-CoV）Answering in medicine
With the structural formula of the teicoplanin class compound is shown in formula I：
I
Wherein R is any of R1, R2, R3, R4 and R5, and R1~R5 structural formulas are as follows：
R1 structural formulas：
R2 structural formulas:
R3 structural formulas:
R4 structural formulas:
R5 structural formulas：
The compound for the structural formula I that the teicoplanin is made of above-mentioned R1~R5 mixes.
The teicoplanin class compound suppresses the envelope protein MERS-CoV-S of Middle East respiration syndrome coronavirus
In application.
The peaceful class compound of the koala suppresses Middle East respiration syndrome coronavirus into the application in host cell.
More specifically, there is provided a kind of teicoplanin class compound is preparing suppression Middle East respiration syndrome coronavirus coating
Application in albumen MERS-CoV-S medicines, the structural formula of the teicoplanin class compound is shown in formula I：
I
Wherein R is any of R1, R2, R3, R4 and R5, and R1~R5 structural formulas are as follows：
R1 structural formulas：
R2 structural formulas:
R3 structural formulas:
R4 structural formulas:
R5 structural formulas：
Test principle：
The present invention using pHIV-luciferase, pCMV- Δ R8.2 and MERS-CoV-S plasmid transfection to 293T cells,
The pseudovirus of Middle East respiration syndrome coronavirus envelope protein can be expressed by packing out, then be infected accordingly with these pseudovirus
Target cell, so as to simulate a kind of state of Middle East respiration syndrome coronavirus infection host cell.
The advantage of the invention is that：
The present invention has listed the chemical combination used with the cell model of such a pseudovirus packaging by screening more than thousand
Thing storehouse, so as to be found that antibiotic teicoplanin can effectively suppress Middle East respiration syndrome coronavirus infection 293T cells
Phenomenon, confirm that the antibiotic teicoplanin has good antivirus action through multiple experiments, IC50 is about 940nM.Separately
Outside, it is a discovery of the invention that teicoplanin can also suppress severe acute respiratory syndrome coronavirus（SARS-CoV）, it passes through suppression
SARS virus processed plays a role into host cell, and IC50 is about 1.18 μM.
This medicine to the security of human body by the inspection of clinical practice, during we determine that teicoplanin resists at present
The obvious drug effect of eastern respiration syndrome coronavirus, avoids the very long cycle of new drug development, this is further researched and developed for us
The strong theoretical foundation and practical basis that anti-Middle East respiration syndrome coronavirus provides, have important Development volue and
Dissemination.Research finds coating egg of the teicoplanin class compound to Middle East respiration syndrome coronavirus according to the present invention
There is inhibitory action in vain.
Compound teicoplanin used in the present invention is purchased from upper sea blue wooden Chemical Co., Ltd.（It is the U.S.
The subsidiary that Selleck Chemicals are set up in Shanghai）.
Brief description of the drawings
Fig. 1 is the antifungal element teicoplanin of various concentrations to Middle East respiration syndrome coronavirus（MERS-CoV）
The inhibition of envelope protein S.
Fig. 2 is suppression effect of the antifungal element teicoplanin of various concentrations to vesicular stomatitis virus coating VSV-G
Fruit.
Fig. 3 is the antifungal element teicoplanin of various concentrations to severe acute respiratory syndrome coronavirus（SARS-
CoV）The inhibition of envelope protein S.
Fig. 4 is inhibition of the antifungal element teicoplanin to influenza A of various concentrations.
Embodiment
The present invention is further described with specific embodiment below in conjunction with the accompanying drawings.Unless otherwise indicated, the present invention uses
Reagent, apparatus and method be conventional reagent, equipment and the conventional use of method purchased in market of the art.
The antifungal element teicoplanin of 1 various concentrations of embodiment is to Middle East respiration syndrome coronavirus（MERS-
CoV）The inhibition of envelope protein S
（1）Bag virus：By 4.5 μ g pHIV-luciferase, 4.5 μ g pCMV- Δs R8.2 and 10 μ g MERS-
CoV-S plasmid transfections are to 293T cells（10 cm dish）, 48 it is small when after, collect viral supernatants, survey p24.
（2）For the screening compound of MERS-CoV-S：By p24-normalized MERS-CoV-S pseudovirus supernatants
（Containing 8 μ g/ml Polybrene）The 293T cells in 96 orifice plates are infected, while add the teicoplanin chemical combination of various concentrations
Thing.
（3）Change liquid：Infect 12 it is small when after, replace fresh DMEM culture mediums.
（4）Detect luciferase activity：Infect 48 it is small when after, washed once with PBS per hole, then add 100 μ l cracking
Liquid, shakes 30 min, takes 10 μ l lysates detection luciferase activity.
Illustrated according to the result figure 1 of embodiment 1, antibiotic teicoplanin specific can act on Middle East breathing synthesis
Levy coronavirus（MERS-CoV）Envelope protein S, suppresses the entrance of MERS-CoV viruses, and thus calculates teicoplanin suppression
The IC50 of MERS-CoV-S is about 940nM.
Suppression of the antifungal element teicoplanin of 2 various concentrations of embodiment to vesicular stomatitis virus coating VSV-G
Effect
（1）Bag virus：By 4.5 μ g pHIV-luciferase, 4.5 μ g pCMV- Δs R8.2 and 10 μ g VSV-G matter
Grain is transfected to 293T cells（10 cm dish）, 48 it is small when after, collect viral supernatants, survey p24.
（2）For the screening compound of VSV-G：By p24-normalized VSV-G pseudovirus supernatants（Containing 8 μ g/ml
Polybrene）The 293T cells in 96 orifice plates are infected, while add the teicoplanin compound of various concentrations.
（3）Change liquid：Infect 12 it is small when after, renew fresh DMEM culture mediums.
（4）Detect luciferase activity：Infect 48 it is small when after, washed once with PBS per hole, then add 100 ul and split
Liquid is solved, shakes 30min, takes 10ul lysates detection luciferase activity.
Illustrate that antibiotic teicoplanin does not have any suppression to the envelope protein of VSV-G according to the result figure 2 of embodiment 2
Effect.
The antifungal element teicoplanin of 3 various concentrations of embodiment is to severe acute respiratory syndrome coronavirus
（SARS-CoV）The inhibition of envelope protein S
（1）Bag virus：By 6.5 μ g pHIV-luciferase, 8 μ g pCMV- Δs R8.2 and 20 μ g SARS-CoV-S
Plasmid transfection is to 293T cells（10 cm dish）, 48 it is small when after, collect viral supernatants, survey p24.
（2）For the screening compound of SARS-CoV-S：By p24-normalized SARS-CoV-S pseudovirus supernatants
（Containing 8 μ g/ml Polybrene）The 293T cells in 96 orifice plates are infected, while add the teicoplanin chemical combination of various concentrations
Thing.
（3）Change liquid：Infect 12 it is small when after, replace fresh DMEM culture mediums.
（4）Detect luciferase activity：Infect 48 it is small when after, washed once with PBS per hole, then add 100 μ l and split
Liquid is solved, shakes 30 min, takes 10 μ l lysates detection luciferase activity.
Illustrated according to the result figure 3 of embodiment 3, antibiotic teicoplanin specific can act on serious acute respiratory
Syndrome coronavirus（SARS-CoV）Envelope protein S, suppresses the entrance of SARS-CoV viruses, and thus calculates teicoplanin
The IC50 for suppressing SARS-CoV-S is about 1.18 μM.
Inhibition of the antifungal element teicoplanin of 4 various concentrations of embodiment to influenza A
（1）Dosing and infection：5 × 104 A549 cells are laid in 24 orifice plates, in 37 DEG C culture 12 it is small when after, add not
Infected with the compound of concentration, and per hole with the influenza A of MOI=0.1, when infection 4 is small after change liquid, 24 it is small when
After collect supernatant.
（2）Measure plaque forming unit（Plaque-forming unit, PFU）：Prepare cell fusion degree >=95%
12 well culture plate of mdck cell, discards cell culture fluid, is washed 2 times with PBS, by 10 times of gradient dilutions of supernatant collected to needs
Dilution factor, each cell hole is inoculated with 500 μ l supernatant dilutions, be placed in 37 DEG C be incubated 1 it is small when.2 × MEM culture mediums are placed in
Preheated at 37 DEG C, while configure 2% low melting-point agarose gel, being completely dissolved to be placed in 50 DEG C of water-baths prevents from solidifying.1 is small
When after discard vial supernatant, with PBS cleaning 2 times, 2% low melting-point agarose gel and 2 × MEM culture mediums 1:1 is mixed and added into
TPCK pancreatin, 0.2% bovine serum albumin(BSA) of final concentration of 2 μ g/ml（BSA）And green grass or young crops-streptomysin of 100U/ml, mix.Per hole
Add 1 ml agarose-MEM culture mediums, after its completely solidification, back-off is positioned over 37 DEG C of CO2 incubators, 48 it is small when after it is right
Plaque carries out observation counting.
Illustrate that antibiotic teicoplanin does not have influenza A any inhibitory action according to the result figure 4 of embodiment 4.
Claims (3)
1. application of the teicoplanin class compound in anti-Middle East respiration syndrome coronavirus pharmaceutical is prepared；
Wherein, the structural formula of the teicoplanin class compound is as shown in Formulas I：
Ⅰ
R is any of R1, R2, R3, R4 and R5 in formula, and R1~R5 structural formulas are as follows：
；
The compound for the structural formula I that the teicoplanin is made of above-mentioned R1~R5 mixes.
2. teicoplanin class compound according to claim 1 is in anti-Middle East respiration syndrome coronavirus pharmaceutical is prepared
Application, it is characterised in that the teicoplanin class compound suppress Middle East respiration syndrome coronavirus envelope protein S
In application.
3. teicoplanin class compound according to claim 1 is in anti-Middle East respiration syndrome coronavirus pharmaceutical is prepared
Application, it is characterised in that the teicoplanin class compound suppress Middle East respiration syndrome coronavirus enter host
Application in cell.
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| CN111671762B (en) * | 2020-01-30 | 2022-02-22 | 沈阳福洋医药科技有限公司 | Application of acylated spiramycin in preparing medicine for treating coronavirus infection disease |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671336A (en) * | 2009-09-23 | 2010-03-17 | 辽宁利锋科技开发有限公司 | Aromatic heterocyclic pyridine derivatives and analogs and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671336A (en) * | 2009-09-23 | 2010-03-17 | 辽宁利锋科技开发有限公司 | Aromatic heterocyclic pyridine derivatives and analogs and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Diazo transger-click reaction reaction route to new lipophilic teicoplanin and ristocetin aglycon dervatives with high antibacterial and anti-influenza viurs activity：an aggregation and receptor binding study;Pinter G. et al.;《J Med Chem》;20091231;第52卷;6053-6061 * |
| Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitrors: synthesis and antiviral studies;bereczki I et al;《bioorganic and medicinal chemistry letters》;20140616;第24卷(第15期);3251-3254 * |
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