CN111467338A - Application of pyroglutamic acid in preparation of medicine for preventing and treating novel coronavirus resistant to new coronary pneumonia - Google Patents
Application of pyroglutamic acid in preparation of medicine for preventing and treating novel coronavirus resistant to new coronary pneumonia Download PDFInfo
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- CN111467338A CN111467338A CN202010266183.7A CN202010266183A CN111467338A CN 111467338 A CN111467338 A CN 111467338A CN 202010266183 A CN202010266183 A CN 202010266183A CN 111467338 A CN111467338 A CN 111467338A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
Abstract
The invention relates to an application of pyroglutamic acid in preparing a medicament for preventing and treating novel coronavirus resistant to new coronary pneumonia, and particularly discloses an application of the pyroglutamic acid or pharmaceutically acceptable salts, isotopes, stereoisomers, a mixture of the stereoisomers, tautomers, esters, amides or prodrugs thereof in preparing the medicament for preventing and/or treating diseases caused by the coronavirus, wherein the coronavirus is novel coronavirus SARS-Cov-2, SARS-CoV, HCoV229E, N L63, OC43, HKU1 and MERS-CoV, the median effective concentration of the pyroglutamic acid to the novel coronavirus resistant to the new coronary pneumonia is 9.34 mu M, the median effective concentration is low, and the antiviral effect is good.
Description
Technical Field
The invention belongs to the field of antiviral drugs, and particularly relates to application of pyroglutamic acid in preparation of a drug for preventing and treating novel coronavirus resistant to new coronary pneumonia.
Background
The novel coronavirus pneumonia (Corona Virus Disease 2019) is an infectious Disease caused by infection of a human body with a novel coronavirus (SARS-Cov-2), and The symptoms of The coronavirus mainly include fever, fatigue, dry cough, dyspnea and renal failure [ The L anancet, 2020,395(10223): 507-513; The L anancet, 2020,395(10223):497 506] coronavirus (Coronavir) belonging to The family Coronaviridae (Coronaviridae) in The systemic classification, and The Virus belonging to The genus Coronaviridae is a positive strand single strand RNA Virus having a coat (envelope) and has a diameter of about 80-120 nm, The genetic material of which is The largest of all RNA viruses, and The coronavirus is generally only infecting human, mouse, pig, cat, dog, avian, and avian glycoproteins (glycoprotein) was first isolated from chicken in 1937 and has a shape of coronavirus particles which is not regular, and has a diameter of about 60-20 nm, and further has a glycoprotein structure of a glycoprotein (glycoprotein belonging to hemagglutinin) of which is expressed by a glycoprotein (glycoprotein belonging to The group of human, mouse, pig, cat, avian, and avian glycoproteins [ glycoprotein ] glycoprotein, and glycoprotein, which has a glycoprotein, a.
The virus particle diameter of SARS-Cov-2 is between 60 and 140nm, the outer envelope has 9 to 12nm prick, the shape is similar to corolla, the genome sequencing shows that SARS-Cov-2 is a single-chain RNA coronavirus, through comparing with other virus sample gene sequence, SARS-Cov-2 is found to be similar to SARS-Cov (79.5%) [ Nature,2020] and bat coronavirus (96%) [ bioRxiv,2020,2020.01.22.914952], and supposing that the virus may be originated from bat [ bioRxiv,2020,2020.01.24.915157; Nature,2020 ]. 2019-nCoV virus belongs to β CoV, which is 7 th member of HCoV family different from SARS-Cov and MERS-CoV [ New England Journal of Medicine,2020], the other 6 members include HCoV 36229 54, OC 57, HKU 82, SARS-Cov and MERS-CoV.
The present invention relates to a new type coronavirus pneumonia, it is a new type coronavirus, it is identical with SARS-CoV coronavirus which is known to cause atypical pneumonia, but its type is different, its fatality rate is lower than SARS-CoV but its infectivity is far higher than SARS-CoV, so that it has no specific medicine which can cure new type coronavirus pneumonia so far, so that the existent therapeutic method is mostly a symptomatic treatment, and its therapeutic effect is poor for some serious patients.
Disclosure of Invention
The invention aims to provide application of L-pyroglutamic acid in preparing a medicine for preventing or treating novel coronavirus resistant to new coronary pneumonia.
Specifically, to solve the technical problem of the present invention, the following technical solutions are adopted:
the invention provides application of pyroglutamic acid or pharmaceutically acceptable salts, isotopes, stereoisomers, mixtures of stereoisomers, tautomers, esters, amides or prodrugs thereof in preparing medicaments for preventing and/or treating diseases caused by coronavirus.
In the technical scheme of the invention, the pyroglutamic acid is L-pyroglutamic acid, D-pyroglutamic acid or a mixture thereof.
In the technical scheme of the invention, the coronavirus is novel coronavirus SARS-Cov-2, SARS-CoV, HCoV229E, N L63, OC43, HKU1 and MERS-CoV.
In the technical scheme of the invention, the disease caused by the coronavirus is pneumonia or a complication thereof caused by any one of SARS-Cov-2, SARS-CoV, HCoV229E, N L63, OC43, HKU1 or MERS-CoV.
In the technical scheme of the invention, L-pyroglutamic acid is shown as a structural formula (1)
In the technical scheme of the invention, pyroglutamic acid or pharmaceutically acceptable salts, isotopes, stereoisomers, mixtures of stereoisomers, tautomers, esters, amides or prodrugs thereof are used as the only active ingredient in the preparation of medicines for preventing and/or treating diseases caused by coronavirus.
In the technical scheme of the invention, pyroglutamic acid or a composition prepared from pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof and other antiviral drugs is used as an active ingredient for preparing drugs for preventing and/or treating diseases caused by coronavirus.
In the technical scheme of the invention, the other antiviral drugs are selected from ganciclovir, acyclovir, amantadine, oseltamivir, abacavir, acemannan, acyclovir sodium, adefovir, alovudine, avsunotol, tricyclodecylamine hydrochloride, alaudine, alitame, adefovir, cidofenac, emtricitabine, cytarabine hydrochloride, delavirdine mesylate, desciclovir, didanosine, dioxaxaline, edexuridine, cimetidine, itracetipine, envilarden, engivir oxime, hopudine, famciclovir hydrochloride, clofenacil, fillibitabine, fexuridine, foscarnet sodium, foscamet sodium, ganciclovir sodium, idovir, indinavir, ethoxybutovidone, lamivudine, lomicrivir, lodenafine, lopinavir, Memantine hydrochloride, methylthioninium chloride, nelfinavir, nevirapine, penciclovir, pirodapvir, ribavirin, saquinavir mesylate, ritonavir, sotalomide hydrochloride, solivudine, penicillin, stavudine, tenofovir, trovudine hydrochloride, valacyclovir hydrochloride, vidarabine phosphate, vidarabine sodium phosphate, tipranavir, viroxime, zalcitabine, zidovudine, and neat oxime.
In another aspect, the present invention provides a pharmaceutical composition for treating or preventing diseases caused by viruses of the family Coronaviridae, comprising pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof.
In the technical scheme of the invention, the pharmaceutical composition also comprises pharmaceutically acceptable auxiliary materials.
In the technical scheme of the invention, the dosage form of the pharmaceutical composition is oral preparation, lung inhalation preparation, mucosa administration preparation, eye preparation or injection.
In the technical scheme of the invention, the oral preparation is selected from granules, powder grinding agents, pills, tablets, capsules or oral liquid.
In another aspect, the invention provides the use of pyroglutamic acid as a disinfectant against viruses of the family Coronaviridae.
Another aspect of the present invention provides a method for treating a disease caused by a virus of the family coronaviridae, comprising administering to a subject a therapeutically effective amount of pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomers, ester or prodrug thereof.
Another aspect of the invention provides a method for preventing infection of a subject with a virus of the family coronaviridae, comprising administering to the subject a therapeutically effective amount of pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester or prodrug thereof, prior to infection.
Advantageous effects
The invention proves the inhibiting effect of pyroglutamic acid on the novel coronavirus of the new coronary pneumonia for the first time, the therapeutic index is high, and the half effective concentration is low; furthermore, pyroglutamic acid is administered before infection to effectively increase the antiviral effect. Pyroglutamic acid is used as an effective drug for treating novel coronavirus infection resistant to new coronary pneumonia.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments of the present invention are described in detail below, but the present invention is not to be construed as limiting the implementable range of the present invention.
Example 1 viral amplification
VeroE6 Vero cells were transformed into 3 × 105One well, inoculated into a 96-well plate, placed in minimal Eagle's minimal basal medium (MEM; GibcoInvitrogen) containing 10% fetal bovine serum (FBS; GibcoInvitrogen) at 37 ℃ with 5% CO2Culturing until the monolayer grows. Diluting new coronavirus clinical isolate 100 times, inoculating to 96-well plate full of monolayer cells, placing at 37 deg.C and 5% CO2Two days of culture (containing normal control).
After two days, the pathological change degree reaches over 75 percent, the mixture is placed in an ultra-low temperature refrigerator at minus 80 ℃, freeze thawing is carried out repeatedly for one time, virus liquid of cell amplification is collected, centrifugation is carried out for 30 minutes at 3000r/min, precipitates are removed, and the mixture is subpackaged into small tubes to be placed in the ultra-low temperature refrigerator at minus 80 ℃ for long-term storage.
Example 2L evaluation of Pyroglutamic acid drug toxicity
L-pyroglutamic acid powder is dissolved in DMSO, diluted with culture solution to 20mg/m L final concentration of 1%, filtered with 0.22 μm filter membrane, stored at 4 deg.C, and stored at 4 deg.C, with a concentration of 2.5 × 10 per well4Inoculating the cells to a 96-well plate, removing culture solution after the cells grow into a monolayer after 24-48 h, adding medicaments with different dilutions l00 mu L per well, adding l00 mu L per well MEM into a normal cell control well, and adding 5% CO at 37 DEG C2Continuously culturing for 2-5 days, adding CCK8 solution (5mg/m L) 20 μ L per well, and placing at 37 deg.C with 5% CO2And (3) continuously incubating for 4 hours in the incubator, removing culture supernatant, adding 00 mu L dimethyl sulfoxide (DMSO) into each hole, oscillating at a low speed for 10 minutes to fully dissolve crystals, selecting 490nm wavelength, and determining the light absorption value of each hole on an enzyme-linked immunosorbent assay monitor.
Example 3L evaluation of the drug efficacy of pyroglutamic acid against the novel coronavirus of New coronopneumonia
To evaluate the antiviral efficacy of the drugs, VeroE6 cells were grown at a density of 5 × 104Cells/well in 48-well cell culture dishes overnight. The virus (MOI 0.05) was added and allowed to infect for 2 hours. Then 2-fold gradient dilution is addedThe drug of (1) is provided with 4 multiple holes in each concentration, the maximum nontoxic concentration is used as the initial concentration of the drug, and the temperature is 34 ℃ and the CO content is 5 percent2Incubating in incubator for 2 days, recording cytopathic Effect (CPE), recording CPE appearing in cell according to 6-grade standard, recording CPE, staining with CCK8, determining OD value, evaluating drug Effect of L-pyroglutamic acid against novel coronavirus of new coronarism (SARS-Cov-2) by CCK8 method to evaluate drug Effect of L-pyroglutamic acid50) 9.34 mu M, and low half effective concentration, which indicates good antiviral effect.
Example 4 immunofluorescence
Immunofluorescence microscopy to detect the expression of viral proteins in VeroE6 cells, cells were fixed with 4% paraformaldehyde and permeabilized with 0.5% TritonX-100, then cells were blocked with 5% Bovine Serum Albumin (BSA) at room temperature for 2 hours, cells were incubated with primary antibody (viral nucleocapsid protein polyclonal antibody of bat SARS-associated coronavirus, Anti-NP, at 1: 1000 dilution) for 2 hours, then incubated with secondary antibody (488Affinipure Donkey Anti-RabbitIgG (H + L), nuclei were stained with Hoechst33258 dye (Beyotime, China).
Claims (10)
1. The use of pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof for the preparation of a medicament for the prophylaxis and/or treatment of diseases caused by coronaviruses.
2. The use of claim 1, wherein the coronavirus is a novel coronavirus, SARS-Cov-2, SARS-CoV, HCoV229E, N L63, OC43, HKU1 and MERS-CoV.
3. The use according to claim 1, wherein the disease caused by coronavirus is infectious disease caused by SARS-Cov-2, SARS-CoV, HCoV229E, N L63, HCoV-OC43, HKU1 or MERS-CoV or its complications, and the infectious disease is preferably respiratory infectious disease.
4. The use according to claim 1 of pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof, as sole active ingredient in the preparation of a medicament for the prevention and/or treatment of diseases caused by coronaviruses; or
The application of pyroglutamic acid or the pharmaceutically acceptable salt, isotope, stereoisomer, mixture of the stereoisomer, tautomer, ester, amide or prodrug thereof and other antiviral drugs as active ingredients in the preparation of drugs for preventing and/or treating diseases caused by coronavirus;
preferably, the other antiviral drug is selected from the group consisting of ganciclovir, acyclovir, amantadine, rimantadine, oseltamivir, abacavir, acemenan, acyclovir sodium, adefovir, alovudine, avrinol, amantadine hydrochloride, amantadine, aliquodine mesylate, avridine, cidofovir, cidofophylline, emtricitabine, cytarabine hydrochloride, delavirdine mesylate, desciclovir, didanosine, dioxazoline, edexuridine, emivirin, itracitabine, emviraden, enviroxime, hoplatin, famciclovir, cloquine hydrochloride, decitabine, felvudine, foscarnet, ganciclovir sodium, idoxural, indinavir, ethoxybutovidone aldehyde, lamivudine, lubucavir, lodenosine, lopinavir hydrochloride, mavir hydrochloride, mavir, trexate, sodium acetate, trematodine, and sodium, Nelfinavir, nevirapine, penciclovir, pirodavir, ribavirin, saquinavir mesylate, ritonavir, hydrochloric acid of sodamide, solivudine, bractenocillin, stavudine, tenofovir, hydrochloric acid of trovudine, valacyclovir hydrochloride, vidarabine, adenosine phosphate, vidarabine sodium phosphate, tipranavir, viroxim, zalcitabine, zidovudine, net oxime.
5. A pharmaceutical composition for treating or preventing a disease caused by a coronavirus, comprising pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof.
6. The pharmaceutical composition of claim 5, further comprising a pharmaceutically acceptable excipient.
7. The pharmaceutical composition according to claim 5, wherein the pharmaceutical composition is in the form of an oral preparation, a pulmonary inhalation preparation, a mucosal administration preparation, an ophthalmic preparation or an injection; preferably, the oral preparation is selected from granules, powders, pills, tablets, capsules or oral liquids.
8. A disinfectant for eliminating contamination by viruses of the family coronaviridae, said disinfectant comprising pyroglutamic acid.
9. A method for treating or preventing a disease caused by a virus of the family coronaviridae, comprising administering to a subject a therapeutically effective amount of pyroglutamic acid or a pharmaceutically acceptable salt, isotope, stereoisomer, mixture of stereoisomers, tautomer, ester, amide or prodrug thereof.
10. The pharmaceutical composition of any one of claims 5-7 or the disinfectant of claim 8 or the method of claim 9, wherein the coronavirus is a novel coronavirus, SARS-Cov-2, SARS-Cov, HCoV229E, N L63, OC43, HKU1, and MERS-Cov.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
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| CN202010266183.7A CN111467338B (en) | 2020-04-07 | 2020-04-07 | Application of pyroglutamic acid in preparation of medicine for preventing and treating novel coronavirus resistant to new coronary pneumonia |
| PCT/CN2020/129184 WO2021203702A1 (en) | 2020-04-07 | 2020-11-16 | Use of pyroglutamic acid in preparation of drugs for preventing and treating novel coronavirus of novel coronavirus pneumonia |
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| CN202010266183.7A CN111467338B (en) | 2020-04-07 | 2020-04-07 | Application of pyroglutamic acid in preparation of medicine for preventing and treating novel coronavirus resistant to new coronary pneumonia |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113350482A (en) * | 2021-05-31 | 2021-09-07 | 中国食品药品检定研究院 | Application of phytohemagglutinin PHA-E in preparation of medicine for treating diseases caused by coronavirus |
| WO2021203702A1 (en) * | 2020-04-07 | 2021-10-14 | 中国科学院深圳先进技术研究院 | Use of pyroglutamic acid in preparation of drugs for preventing and treating novel coronavirus of novel coronavirus pneumonia |
| WO2022088037A1 (en) * | 2020-10-30 | 2022-05-05 | 中国科学院深圳先进技术研究院 | Application of sirtinol in preparation of drug for preventing and treating coronavirus |
| WO2022088038A1 (en) * | 2020-10-30 | 2022-05-05 | 中国科学院深圳先进技术研究院 | Application of cay10603 in preparation of drugs for preventing and treating coronavirus-related diseases |
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| US7569530B1 (en) * | 2003-06-20 | 2009-08-04 | The Procter & Gamble Company | Antimicrobial compositions, products and methods employing same |
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| CN111467338B (en) * | 2020-04-07 | 2021-04-23 | 中国科学院深圳先进技术研究院 | Application of pyroglutamic acid in preparation of medicine for preventing and treating novel coronavirus resistant to new coronary pneumonia |
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2020
- 2020-04-07 CN CN202010266183.7A patent/CN111467338B/en active Active
- 2020-11-16 WO PCT/CN2020/129184 patent/WO2021203702A1/en active Application Filing
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| CN1411372A (en) * | 1999-10-19 | 2003-04-16 | 宝洁公司 | Antimicrobial compositions comprising pyroglutamic acid and optionally metal salts |
| US20040234457A1 (en) * | 1999-10-19 | 2004-11-25 | The Procter & Gamble Company | Methods of preventing and treating SARS using low pH respiratory tract compositions |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021203702A1 (en) * | 2020-04-07 | 2021-10-14 | 中国科学院深圳先进技术研究院 | Use of pyroglutamic acid in preparation of drugs for preventing and treating novel coronavirus of novel coronavirus pneumonia |
| WO2022088037A1 (en) * | 2020-10-30 | 2022-05-05 | 中国科学院深圳先进技术研究院 | Application of sirtinol in preparation of drug for preventing and treating coronavirus |
| WO2022088038A1 (en) * | 2020-10-30 | 2022-05-05 | 中国科学院深圳先进技术研究院 | Application of cay10603 in preparation of drugs for preventing and treating coronavirus-related diseases |
| CN113350482A (en) * | 2021-05-31 | 2021-09-07 | 中国食品药品检定研究院 | Application of phytohemagglutinin PHA-E in preparation of medicine for treating diseases caused by coronavirus |
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| Publication number | Publication date |
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| WO2021203702A1 (en) | 2021-10-14 |
| CN111467338B (en) | 2021-04-23 |
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