CN104844666B - The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects - Google Patents
The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects Download PDFInfo
- Publication number
- CN104844666B CN104844666B CN201510148401.6A CN201510148401A CN104844666B CN 104844666 B CN104844666 B CN 104844666B CN 201510148401 A CN201510148401 A CN 201510148401A CN 104844666 B CN104844666 B CN 104844666B
- Authority
- CN
- China
- Prior art keywords
- influenza virus
- compound
- imide compounds
- naphthoyl imide
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention relates to a kind of naphthoyl imide compounds containing glycosyl and application thereof.The concrete structure of naphthoyl imide compounds disclosed by the invention containing glycosyl is see specification Chinese style I or II.The naphthoyl imide compounds containing glycosyl that the present invention is designed and synthesized can go out the presence of avian influenza virus (such as H5N1, H7N9 or H10N8) or human influenza virus (such as H1N1 or H3N2) with Sensitive Detection.
Description
Technical field
The present invention relates to a kind of naphthoyl imide compounds containing glycosyl and application thereof, specifically, it is related to a kind of containing saliva
The naphthoyl imide compounds of liquid acid glycosyl and its application in influenza virus detects.
Background technology
Avian influenza virus generally only infects birds, but due to virus variation, makes avian influenza virus across kind of propagation to infect
People, animal and other animals.So far find that the avian influenza virus subtype of energy direct infection people has：H5N1、H7N1、H7N2、H7N3、
H7N7, H9N2, H7N9 and H10N8 etc..After avian flu virus infection people, morbidity is anxious, the course of disease is short, fatal rate is high, therefore should
Viroid causes significant damage to human life and health.In history avian influenza virus once caused repeatedly it is global be very popular, lead
Cause countless personnel deaths and serious economic loss.For example, the H5N1 influenza pandemic of Hong Kong outburst in 1997,2013 in South China
The H7N9 influenza pandemic of side's outburst, not only causes serious threat, and produce weight to social economy to mankind's public health security
Big influence.Therefore, quick to avian influenza virus, convenient, economization novel detection method is built, for preventing and controlling big face
Product bird flu prevalence has extremely important social effect and economic value.
Mainly there are ELISA, neutralizing antibody to detect, gather currently for the diagnostic method of avian influenza virus
Synthase chain reaction method etc..Although such method has higher sensitivity, but its equipment is expensive, cumbersome, is difficult popularization
Using.Therefore, develop and a kind of be efficiently applied to that avian influenza virus is simple, quick, new method that is accurately detecting is the current world
Upper sciences problems urgently to be resolved hurrily.
The content of the invention
The present inventor has designed and synthesized two kinds based on the glimmering of glycosyl naphthalimide through extensive and in-depth study
Light probe compound.Found through experiment：By fluorescent spectrometry, the glycosyl naphthoyl imide compounds of formula I can be with sensitive inspection
Avian influenza virus (such as H5N1, H7N9 or H10N8) presence is measured, the glycosyl naphthoyl imide compounds of formula II can spirit
The quick presence for detecting human influenza virus (H1N1 or H3N2) etc..I.e. in the presence of virus, a kind of " folding can occur for correspondent probe
Folded-unfolding " process, promotes its fluorescence at 540nm wavelength to be significantly increased with the increase of virus titer.In addition, probe
Available for the risk for assessing the large area propagation in crowd of above-mentioned avian influenza virus.Therefore, glycosyl naphthalimide of the present invention
Compound can be used as the class novel fluorescence probe for detecting avian influenza virus.
It is an advantage of the invention to provide naphthoyl imide compounds of the class containing glycosyl.
Naphthoyl imide compounds of the present invention are compound shown in formula I or II, or it is pharmacologically acceptable
Salt：
It is another object of the present invention to disclose a kind of purposes of the above-mentioned naphthoyl imide compounds containing glycosyl, i.e.,
Compound shown in formula I or II, or its pharmacologically acceptable salt as detection avian influenza virus or human influenza virus it is glimmering
The application of light probe.In other words, compound shown in formula I or II, or its pharmacologically acceptable salt prepare detection fowl stream
Application in Influenza Virus or the fluorescence probe of human influenza virus.
Brief description of the drawings
Fig. 1 is with different avian influenza virus H 5 N 1 concentration, the fluorescence spectrum change curve of chemical compounds I；
Fig. 2 is with different avian influenza virus H7N9 concentration, the fluorescence spectrum change curve of chemical compounds I；
Fig. 3 is with different avian influenza virus H10N8 concentration, the fluorescence spectrum change curve of chemical compounds I；
Fig. 4 is with different virus particle and the reacted Fluorescence Increasing degree (F/F of chemical compounds I0) block diagram；
Fig. 5 is with different human influenza virus H3N2 concentration, compound II fluorescence spectrum change curve；
Fig. 6 is with different human influenza virus H1N1 concentration, compound II fluorescence spectrum change curve；
Fig. 7 is with different virus particle and the reacted Fluorescence Increasing degree (F/F of compound II0) block diagram.
Embodiment
By embodiment and Figure of description, the present invention is further elaborated.
Embodiment 1
The preparation of compound shown in Formulas I and Formula II (being abbreviated as compound I and compound II, similarly hereinafter)：
The route of compound is as follows shown in synthesis type I and Formula II
(1) compound IV preparation：
Compound III (638mg, 1.6mmol) is dissolved in 15mL DMF, Sodium azide is slowly added to
(312mg, 4.8mmol), reaction system is warming up to 60 DEG C, and after TLC detection reactions completely, vacuum distillation removes solvent, and uses silicon
Glue post separation, obtains 450mg yellow solids (compound IV), yield 81%.
Wherein, compound III synthesis step is referring to A.Pain, S.Samanta, S.Dutta, A.K.Saxena,
M.Shanmugavel,H.Kampasi,G.N.Quazi,U.Sanyal,Acta Poloniae Pharmaceutica,2003,
60,285-291。
1H NMR(400MHz,CDCl3) δ 8.68 (d, J=7.3Hz, 1H), 8.61 (d, J=8.5Hz, 1H), 8.44 (d, J
=7.9Hz, 1H), 8.06 (d, J=7.9Hz, 1H), 7.87 (t, J=7.9Hz, 1H), 4.61 (t, J=7.1Hz, 2H), 3.67
(t, J=7.1Hz, 2H)
(2) compound V preparation：
Compound IV (431mg, 1.25mmol) is dissolved in 20mL glycol monoethyl ether, ethylenediamine is slowly added dropwise
(0.2mL, 2.5mmol's), reaction system is warming up to 90 DEG C, and after TLC detection reactions completely, vacuum distillation removes solvent, is used in combination
Silica gel post separation, obtains the red color solids (compound V) of 319mg, yield 79%.
1H NMR(400MHz,d6- DMSO) δ 8.73 (d, J=8.4Hz, 1H), 8.48-8.44 (m, 1H), 8.29 (d, J=
8.6Hz, 1H), 7.71 (dd, J=8.3,7.4Hz, 1H), 6.83 (t, J=7.2Hz, 1H), 4.27 (t, J=6.1Hz, 2H),
3.59 (t, J=6.1Hz, 4H), 2.95 (t, J=6.4Hz, 2H)
HR-ESI-MS:m/z[M+H]+calcd for C16H17N6O2325.1408,found 325.1419.
(3) compound VI preparation：
1- pyrenes butyric acid (558mg, 1.72mmol) is dissolved in 40mL dichloromethane, EDC is added under the conditions of 0 DEG C
Compound V (500mg, 1.72mmol), reactant are added after (989mg, 5.16mmol) and HOBt (348mg, 2.58mmol), 1h
System is warming up to room temperature, and after TLC detection reactions completely, vacuum distillation removes solvent, and uses silica gel post separation, obtains 671mg yellow and consolidates
Body (compound VI), yield 65%.
1H NMR(400MHz,d6- DMSO) δ 8.59 (d, J=7.6Hz, 1H), 8.34 (d, J=6.5Hz, 1H), 8.26
(dd, J=14.9,7.4Hz, 3H), 8.17 (d, J=7.8Hz, 2H), 8.13-8.10 (m, 2H), 8.05 (t, J=7.6Hz,
1H), 7.86 (d, J=7.8Hz, 1H), 7.65-7.58 (m, 1H), 6.86 (d, J=8.7Hz, 1H), 4.20 (t, J=6.0Hz,
2H), 3.52 (dd, J=20.9,14.7Hz, 5H), 3.26-3.19 (m, 2H), 2.26 (d, J=7.1Hz, 2H), 2.00 (d, J=
7.3Hz,3H).
HR-ESI-MS:m/z[M+H]+calcd for C36H31N6O3595.2452,found 595.2457.
(4) compound VII preparation：
By compound VI (390mg, 0.656mmol) and compound N-Boc-O- propargyls oxyammonia (112mg,
(a small amount of H is added dropwise in the dichloromethane for 0.656mmol) being dissolved in 20mL2O in), add cupric sulfate pentahydrate (329mg, 1.31mmol) and
Sodium ascorbate (524mg, 2.62mmol), after TLC detection reactions completely, vacuum distillation removes solvent, and uses silica gel post separation,
Obtain 426mg yellow solids (compound VII), yield 85%.
1H NMR(400MHz,d6- DMSO) δ 8.59 (d, J=7.6Hz, 1H), 8.34 (d, J=6.5Hz, 1H), 8.26
(dd, J=14.9,7.4Hz, 3H), 8.17 (d, J=7.8Hz, 2H), 8.13-8.10 (m, 2H), 8.05 (t, J=7.6Hz,
1H), 7.86 (d, J=7.8Hz, 1H), 7.62 (s, 1H), 7.60-7.58 (m, 1H), 6.86 (d, J=8.7Hz, 1H), 4.20
(t, J=6.0Hz, 4H), 3.52 (dd, J=20.9,14.7Hz, 5H), 3.26-3.19 (m, 2H), 2.26 (d, J=7.1Hz,
2H), 2.00 (d, J=7.3Hz, 3H), 1.67 (s, 9H)
HR-ESI-MS:m/z[M+H]+calcd for C44H44N7O6766.3353,found 766.3353.
(5) compound VIII preparation：
Compound VII (50mg, 0.066mmol) is dissolved in 10mL dichloromethane, is slowly added dropwise under the conditions of 0 DEG C
4mL trifluoroacetic acids, after TLC detection reactions completely, vacuum distillation removes solvent, and uses silica gel post separation, obtains 37mg yellow solids
(compound VIII), yield 86%.
1H NMR(400MHz,d6- DMSO) δ 8.59 (d, J=7.6Hz, 1H), 8.34 (d, J=6.5Hz, 1H), 8.26
(dd, J=14.9,7.4Hz, 3H), 8.17 (d, J=7.8Hz, 2H), 8.13-8.10 (m, 2H), 8.05 (t, J=7.6Hz,
1H), 7.86 (d, J=7.8Hz, 1H), 7.62 (s, 1H), 7.60-7.58 (m, 1H), 6.86 (d, J=8.7Hz, 1H), 4.20
(t, J=6.0Hz, 4H), 3.52 (dd, J=20.9,14.7Hz, 5H), 3.26-3.19 (m, 2H), 2.26 (d, J=7.1Hz,
2H), 2.00 (d, J=7.3Hz, 3H)
HR-ESI-MS:m/z[M+H]+calcd for C39H36N7O4666.2823,found 666.2832.
(6) compound I preparation：
Compound VIII (20mg, 0.03mmol) and 3 '-Sialylactose (38mg, 0.06mmol) are dissolved in 12mL's
In the dicyandiamide solution of acetonitrile/water (2/1, v/v), be slowly dropped into acetic anhydride (0.3mL, 0.45mmol) and aniline (0.15mL,
0.15mmol), after TLC detections reaction completely, vacuum distillation removes solvent, and uses silica gel post separation, obtains (the change of 32mg yellow solids
Compound I), yield 84%.
1H NMR(400MHz,d6- DMSO) δ 8.59 (d, J=8.3Hz, 1H), 8.32-8.23 (m, 5H), 8.18-8.03
(m, 7H), 7.87 (d, J=7.9Hz, 2H), 7.62 (s, 1H), 6.87 (d, J=8.8Hz, 1H), 5.41 (d, J=9.1Hz,
2H), 5.33 (d, J=5.1Hz, 1H), 5.22 (s, 2H), 4.94 (d, J=5.7Hz, 2H), 4.67 (d, J=5.6Hz, 2H),
4.57-4.50 (m, 2H), 4.36 (d, J=8.2Hz, 1H), 3.94 (d, J=5.8Hz, 2H), 3.67 (d, J=17.2Hz, 4H),
3.56-3.40 (m, 10H), 3.29-3.16 (m, 4H), 2.67 (s, 1H), 2.27 (d, J=6.8Hz, 3H), 2.02 (s, 3H),
1.95(s,2H)；
HR-ESI-MS:m/z[M+H]+calcd for C62H72N8O22:1281.4845,found:1281.4849.
(7) compound II preparation：
Compound VIII (20mg, 0.03mmol) and 6 '-Sialylactose (38mg, 0.06mmol) are dissolved in 12mL's
In the dicyandiamide solution of acetonitrile/water (2/1, v/v), be slowly dropped into acetic anhydride (0.3mL, 0.45mmol) and aniline (0.15mL,
0.15mmol), after TLC detections reaction completely, vacuum distillation removes solvent, and uses silica gel post separation, obtains (the change of 30mg yellow solids
Compound II), yield 80%.
1H NMR(400MHz,d6- DMSO) δ 8.59 (d, J=8.3Hz, 1H), 8.32-8.22 (m, 5H), 8.18-8.04
(m, 7H), 7.87 (d, J=7.9Hz, 2H), 7.62 (s, 1H), 6.87 (d, J=8.8Hz, 1H), 5.41 (d, J=9.1Hz,
2H), 5.33 (d, J=5.1Hz, 1H), 5.22 (s, 2H), 4.94 (d, J=5.7Hz, 1H), 4.67 (d, J=5.6Hz, 2H),
4.57-4.50 (m, 2H), 4.36 (d, J=8.2Hz, 1H), 3.94 (d, J=5.8Hz, 2H), 3.67 (d, J=17.2Hz, 4H),
3.54-3.40 (m, 10H), 3.29-3.18 (m, 4H), 2.67 (s, 1H), 2.27 (d, J=6.8Hz, 3H), 1.98 (d, J=
28.9Hz,3H),1.95(s,2H)；
HR-ESI-MS:m/z[M+H]+calcd for C62H72N8O22:1281.4845,found:1281.4849.
Embodiment 2
By the application of the chemical compounds I prepared in embodiment 1 and compound II in detection avian influenza virus,
Its concrete operation method and result are as follows：
1mL PBS cushioning liquid, the DMSO of 1 μ L 5mM chemical compounds Is are sequentially added into 1cm × 1cm × 4cm cuvette
Solution, prepares the chemical compounds I solution that concentration is 5 μM.Successively into above-mentioned solution add concentration gradient rise H5N1, H7N9 and
H10N8 PBS solution, and determine its fluorescent spectrum curve (Fig. 1, Fig. 2 and Fig. 3).From Fig. 1, Fig. 2 and Fig. 3 can be seen that with
Fluorescence emission peak in system at the increase of influenza virus concentration titre, 540nm is gradually increasing, and fluorescence spectrum presents a kind of
The change of " enhanced ".
Respectively to above-mentioned concentration for added in 5 μM of chemical compounds I solution same concentrations H1N1, H3N2, H5N1, H7N9 and
H10N8 PBS solution, and determine its fluorescent spectrum curve (Fig. 4).From fig. 4, it can be seen that chemical compounds I only to mainly in combination with
Avian influenza virus H 5 N 1, H7N9 and the H10N8 of Neu5Aca2,3Gal acceptor have " enhanced " response, and to mainly in combination with
Human influenza virus H1N1 and H3N2 of Neu5Aca2,6Gal acceptor etc. without obvious responsing to, illustrate that probe I has to avian influenza virus
Standby high selectivity.
1mL PBS cushioning liquid is sequentially added into 1cm × 1cm × 4cm cuvette, 1 μ L 5mM compounds II's
DMSO solution, prepares the compound II solution that concentration is 5 μM.Successively into above-mentioned solution add concentration gradient rise H1N1 and
H3N2 PBS solution, and determine its fluorescent spectrum curve (Fig. 5 and Fig. 6).From figs. 5 and 6, it can be seen that being flowed with system
Fluorescence emission peak at the increase of Influenza Virus concentration titre, 540nm is gradually increasing, and fluorescence spectrum is presented a kind of " enhanced "
Change.
Respectively to above-mentioned concentration H1N1, H3N2, H5N1, H7N9 for addition same concentrations in 5 μM of compound II solution
With H10N8 PBS solution, and its fluorescent spectrum curve (Fig. 7) is determined.From figure 7 it can be seen that chemical compounds I is to that can combine
H1N1, H3N2 and H7N9 virus of Neu5Aca2,6Gal acceptor have " enhanced " response, and to only combining Neu5Aca2,3Gal
H5N1 and H10N8 viruses of acceptor etc. without obvious responsing to, illustrate that I pairs of probe I can combine Neu5Aca2, the influenza of 6Gal acceptors
Virus possesses high selectivity, can be further used for assessing the influenza virus risk that large area is propagated in crowd.
Claims (3)
1. a kind of naphthoyl imide compounds containing glycosyl, the naphthoyl imide compounds are compound shown in Formulas I or II, or
It is in pharmacologically acceptable salt：
2. compound shown in Formulas I as claimed in claim 1, or it detects bird flu preparing in pharmacologically acceptable salt
Application in the fluorescence probe of virus；
Wherein described avian influenza virus is：H5N1, H7N9 or H10N8.
3. compound shown in Formula II as claimed in claim 1, or it detects the stream of people preparing in pharmacologically acceptable salt
Application in the fluorescence probe of Influenza Virus；
Wherein described human influenza virus is：H1N1 or H3N2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510148401.6A CN104844666B (en) | 2015-03-31 | 2015-03-31 | The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510148401.6A CN104844666B (en) | 2015-03-31 | 2015-03-31 | The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104844666A CN104844666A (en) | 2015-08-19 |
| CN104844666B true CN104844666B (en) | 2017-08-22 |
Family
ID=53844694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510148401.6A Active CN104844666B (en) | 2015-03-31 | 2015-03-31 | The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104844666B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109212207B (en) * | 2018-10-12 | 2019-08-20 | 北京理工大学 | For detecting fluorescent reagent of influenza virus hemagglutinin albumen and preparation method thereof and detection method in oral cavity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2533039T (en) * | 2008-04-24 | 2017-04-13 | Max-Planck-Gesellschaft Zur Förderung Der Wss E V | Method for automated high throughput identification of carbohydrates and carbohydrate mixture composition patterns as well as systems therefore |
| CN101519648A (en) * | 2009-01-05 | 2009-09-02 | 中国科学院广州生物医药与健康研究院 | Fluorescent cell model for screening M2 ion channel blocker for influenza virus and application method thereof |
| JP5285022B2 (en) * | 2010-04-30 | 2013-09-11 | 旭化成株式会社 | Glycopeptide derivative and method for producing the same |
| CN103788159B (en) * | 2014-01-20 | 2016-02-24 | 华东理工大学 | Avrmectin B 1afluorescent marker and application thereof |
| CN104017039B (en) * | 2014-06-11 | 2016-02-24 | 华东理工大学 | Containing glycosyl naphthoyl imide compounds and uses thereof |
-
2015
- 2015-03-31 CN CN201510148401.6A patent/CN104844666B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN104844666A (en) | 2015-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Nogales et al. | Replication-competent influenza A viruses expressing a red fluorescent protein | |
| US9987282B2 (en) | Small molecule inhibitors of influenza A RNA-dependent RNA polymerase | |
| CN104774199B (en) | 2‑（2 benzyl hydrazono-s）‑5‑（1,2,4 triazole, 1 base）Thiazole and its preparation and application | |
| CN106232119B (en) | Small molecule inhibitors of influenza A RNA-dependent RNA polymerase | |
| CN104844666B (en) | The naphthoyl imide compounds of glycosyl containing sialic acid and its application in influenza virus detects | |
| Jang et al. | Synthesis and anti-influenza virus activity of 4-oxo-or thioxo-4, 5-dihydrofuro [3, 4-c] pyridin-3 (1H)-ones | |
| CN103705506B (en) | Application of enilconazole in preparing drug for treating or preventing influenza virus infections | |
| CN103720687B (en) | The application of dicoumarol in the medicine preparing treatment or flu-prevention viral infection | |
| CN104817539B (en) | 2 phenoxyquinoxaline derivatives and its medical usage | |
| Eierhoff et al. | The influenza A virus matrix protein as a marker to monitor initial virus internalisation | |
| CN103705497B (en) | Application of liothyronine in preparation of medicine for treatment or prevention of influenza virus infection | |
| CN103720684B (en) | The application of bentrl hydrothloride in preparation treatment or flu-prevention virus infective medicament | |
| CN103705516B (en) | The application of chloroxine in the medicine preparing treatment or flu-prevention viral infection | |
| CN103690517B (en) | Application of dithranol to preparation of medicament for treating or preventing influenza virus infection | |
| CN106317049B (en) | 2- [5- (nitrogen azoles -1- bases) thiazole -2- imino groups] application of -5- benzal -4- thiazolinones as NA inhibitor | |
| CN104814973B (en) | Application in the drug of diseases associated with inflammation of the Cappariloside A in preparation for treating influenza and influenza virus mediation | |
| CN106117172B (en) | The application of naphtho- [1,2-b] furans -4,5- diketone -2- sulfonic acids and its salt on preparing antitumor drug | |
| CN103690522B (en) | Application of nafronyloxalate in preparing medicine for treating or preventing influenza virus | |
| CN105085480B (en) | 2‑[4‑（The epoxide of quinoxaline 2）Phenoxy group] fatty acyl pyridine amine medical usage | |
| CN105753857B (en) | The medical usage of benzyl imino thiazole methylquinoline ketone derivatives | |
| Yi et al. | Phylogenetic and molecular analysis of an H7N7 avian influenza virus isolated in east dongting lake in 2012 | |
| US10323012B2 (en) | Miliusanes as antiviral agents | |
| CN103251590B (en) | Application of doxylamine succinate in preparing drug for treating or preventing influenza virus | |
| CN103893187B (en) | The application of trimeprimine in preparation treatment or flu-prevention virus infective medicament | |
| WO2022135136A1 (en) | Tuberculatin analogs as antiviral agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |