CN112645874B - Lysosome targeting fluorescent probe and preparation method and application thereof - Google Patents
Lysosome targeting fluorescent probe and preparation method and application thereof Download PDFInfo
- Publication number
- CN112645874B CN112645874B CN202011547009.6A CN202011547009A CN112645874B CN 112645874 B CN112645874 B CN 112645874B CN 202011547009 A CN202011547009 A CN 202011547009A CN 112645874 B CN112645874 B CN 112645874B
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- lysosome
- compound
- lysosomal
- targeting fluorescent
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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
- G01N11/00—Investigating flow properties of materials, e.g. viscosity, plasticity; Analysing materials by determining flow properties
-
- 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
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N11/00—Investigating flow properties of materials, e.g. viscosity, plasticity; Analysing materials by determining flow properties
- G01N2011/006—Determining flow properties indirectly by measuring other parameters of the system
- G01N2011/008—Determining flow properties indirectly by measuring other parameters of the system optical properties
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a lysosome targeting fluorescent probe, a preparation method and application thereof, wherein triphenylamine monoaldehyde derivatives with strong electron donating ability react with 2-methylquinoline iodized salt with strong electron withdrawing ability to simply and efficiently prepare the lysosome targeting fluorescent probe with D-pi-A configuration, the maximum emission peak is about 646nm, and the fluorescence intensity is obviously enhanced along with the increase of viscosity; the laser confocal microscopic imaging result shows that the lysosome targeting fluorescent probe prepared by the invention can penetrate cell membranes and target lysosome parts in cells, and the probe has better light stability, so that the lysosome targeting fluorescent probe can monitor viscosity change, fusion and migration processes of lysosomes in real time.
Description
Technical Field
The invention belongs to the technical field of molecular probes, and particularly relates to a lysosome targeting fluorescent probe, and a preparation method and application thereof.
Background
In living bodies, intracellular viscosity plays a very important role in controlling information transmission, substance transport, interactions between biomacromolecules, and the like. Abnormalities in intracellular viscosity are closely related to cellular dysfunction and many diseases such as Alzheimer's disease, arteriosclerosis, cellular malignancy, diabetes, and the like. Lysosomes are found in almost all animal cells, are vesicle-like organelles surrounded by a monolayer membrane and containing various acid hydrolases, and have the main functions of performing digestion in the cells and playing an important role in maintaining normal metabolic activities and defenses of the cells. As a digestive organ of cells, lysosomes are accompanied by changes in viscosity during the process of absorbing and degrading biological macromolecules. In addition, if a certain hydrolase is lacking in the lysosome due to a genetic defect, the corresponding substrate cannot be degraded and accumulated in the lysosome, so that the lysosome is overloaded to cause lysosomal storage disease. Therefore, monitoring the viscosity change in lysosomes is of great application value.
In recent years, confocal laser fluorescence microscopy imaging has become an indispensable research tool for research in the biomedical field. Compared with the common fluorescence microscopic imaging technology, the laser confocal fluorescence microscopic imaging technology has the advantages that: high spatial resolution and selectivity, small signal interference, etc., provides a sharper tool for developing and analyzing dynamic processes of living cells and tissues. However, most of the current lysosome viscosity fluorescent probes have short emission wavelength (< 600 nm), are easily interfered by the autofluorescence of the blue-green area in the cell, have low tissue penetration depth and are not beneficial to biological imaging.
Disclosure of Invention
In order to solve the technical problems, the invention provides a lysosome targeting fluorescent probe, the maximum emission peak of which is about 646nm, and the interference of autofluorescence in a living body can be eliminated, so that the background noise is reduced, the signal-to-noise ratio is improved, and the lysosome targeting fluorescent probe has smaller photodamage and stronger permeability.
The invention also provides a preparation method of the lysosome targeting fluorescent probe, which has the advantages of easily available raw materials, low cost, mild reaction conditions, simple post-treatment and higher yield, and makes commercialization possible.
The invention also provides application of the lysosome targeting fluorescent probe in lysosome labeling or lysosome viscosity change monitoring or lysosome fusion and migration monitoring in real time, which can penetrate cell membranes, target lysosome parts in cells and track the fusion and migration processes of lysosomes; and as the lysosome viscosity increases, the fluorescence intensity increases.
The invention also provides a method for carrying out lysosome labeling by utilizing the lysosome targeting fluorescent probe, which is characterized in that biological cells and the lysosome targeting fluorescent probe are jointly cultured for 20 minutes, and are developed by utilizing a laser confocal microscope.
In order to achieve the above purpose, the invention adopts the following specific technical scheme:
a lysosome targeting fluorescent probe, the lysosome targeting fluorescent probe having the structural formula:
the preparation method of the lysosome targeting fluorescent probe provided by the invention comprises the following steps: dissolving a compound M1 and a compound M2 in an organic solvent, carrying out reflux reaction by taking organic base as a catalyst, cooling to room temperature after the reaction is finished, and carrying out suction filtration, washing and drying to obtain the lysosome targeted fluorescent probe;
the structural formula of the compound M1 is as follows:
the structural formula of the compound M2 is as follows:
further, the organic solvent is ethanol; the organic base is piperidine.
The ratio of the amounts of the substances of the compound M1, the compound M2 and the catalyst is 1:1.1 to 1.2:0.6 to 0.7, preferably 1:1.13:0.67.
the concentration of the compound M1 relative to the organic solvent is 0.05 to 0.1M, preferably 0.06M.
The time of the reflux reaction is 22 to 26 hours, preferably 24 hours.
The invention prepares the triphenylamine derivative lysosome targeting fluorescent probe with D-pi-A configuration simply and efficiently by reacting the triphenylamine monoaldehyde derivative with strong electron donating ability with the 2-methylquinoline iodized salt with strong electron withdrawing ability, the maximum emission peak is about 646nm, and the fluorescence intensity is obviously enhanced along with the increase of viscosity. Laser confocal microscopic imaging results show that the lysosome targeting fluorescent probe prepared by the invention can penetrate cell membranes and target lysosome parts in cells. Because the probe has better light stability, the probe can monitor the fusion and migration process of the lysosome in real time.
The invention has the following beneficial effects:
1. the lysosome targeted fluorescent probe provided by the invention has the advantages of easily available synthetic raw materials, low cost, mild reaction conditions, simple post-treatment and higher yield, and is possible to commercialize.
2. The emission wavelength of the lysosome targeted fluorescent probe provided by the invention is about 646nm, so that the biological background can be effectively reduced, and the signal-to-noise ratio of biological imaging can be improved.
3. The fluorescence intensity of the lysosome targeted fluorescent probe provided by the invention is obviously enhanced along with the increase of viscosity, and the fluorescence intensity can be enhanced to 458 times.
4. The lysosome targeting fluorescent probe provided by the invention is a fluorescent probe which can target lysosomes in cells and can monitor the viscosity change of the lysosomes.
5. The lysosome targeting fluorescent probe provided by the invention can track the fusion and migration process of lysosomes in real time.
6. Compared with a commercial lysosome probe, the lysosome targeting fluorescent probe has larger Stokes shift, the excitation wavelength is 514nm, the emission wavelength is 646nm, the Stokes shift is 132nm, and the background interference can be reduced.
Drawings
FIG. 1 is a synthetic route diagram of a lysosomal targeted fluorescent probe;
FIG. 2 is a nuclear magnetic resonance spectrum of the lysosome targeted fluorescent probe prepared in example 1;
FIG. 3 is an infrared spectrum of a lysosome targeting fluorescent probe prepared in example 1;
FIG. 4 is a mass spectrum of the lysosomal targeting fluorescent probe prepared in example 1;
FIG. 5 is a fluorescence emission spectrum (A) of the lysosomal targeted fluorescent probe prepared in example 1 in different volume fractions of water/glycerol viscous medium; fluorescence histogram after interaction of compound L with amino acids, BSA, DNA, RNA, wherein: l-phenylalanine, 2.L-alanine, 3.BSA, 4.L-cysteine, 5.DNA, 6.GSH, 7.L-glutamic acid, 8.L-histidine, 9.L-leucine, 10.L-proline, 11.RNA, 12.L-serine, 13.L-threonine, 14.L-valine, 15.L-arginine, 16, L-tyrosine, 17.99% glycerol (B);
FIG. 6 is the results of the lysosomal targeting fluorescent probe prepared in example 1 and co-localized human hepatoma cells with commercial dyes having different targeting functions: wherein, figures A1-A4 are the development diagrams of the compound L after the compound L acts on human liver cancer cells; FIGS. B1-B4 correspond to the development results after co-incubation of commercial dyes with Compound L, lysotracker green (lysosome commercial dye), mitotracker green (mitochondrial commercial dye), hoechst 33342 (nucleus commercial dye), LCS LipidTOX Deep Red (lipid droplet commercial dye), respectively; FIGS. C1-C4 correspond to the superposition results of FIGS. A1-A4 and FIGS. B1-B4, respectively; figures D1-D4 correspond to pearson coefficient values for co-localization results, respectively;
FIG. 7 is a graph showing the image of cells after 20 minutes of incubation of the lysosomal targeting fluorescent probe prepared in example 1 with human hepatoma cells, without addition of (A) and with addition of (B) dexamethasone;
FIG. 8 is a photograph of a cell image of a lysosome-targeted fluorescent probe prepared in example 1 incubated with human hepatoma cells for 20 minutes, followed by a 30-minute incubation with chloroquine solution.
Detailed Description
The present invention will be described in detail with reference to examples.
The synthetic process reference CrystEngComm,2017,19:6489-6497 for the compound M1 used in the present invention; synthetic methods for compound M2 reference angelw.chem.int.ed., 2018,57:16506-16510.
Example 1
A lysosome targeted fluorescent probe (compound L) having the structural formula:
the synthetic route of the lysosome targeted fluorescent probe is shown in figure 1, and the preparation method comprises the following steps:
in a 100mL round bottom flask, M1 (0.43 g,1.5 mmol), M2 (0.48 g,1.7 mmol) and 25mL ethanol were added sequentially, 100. Mu.L piperidine was used as a catalyst, the mixture was refluxed for 24 hours, cooled to room temperature, solid was precipitated, filtered under reduced pressure, the filter cake was washed 3 times with ethanol, and dried under vacuum for 12 hours to obtain 0.68g of a purple black solid with a yield of 81.9%. And the infrared, hydrogen spectrum and mass spectrum characterization is carried out, and the result is as follows:
1 H NMR(400MHz,d 6 -DMSO) δ 8.45-8.40 (d, 1H), 8.26-8.02 (m, 4H), 7.94-7.88 (m, 1H), 7.76-7.63 (m, 2H), 7.49-7.33 (m, 5H), 7.16-7.10 (m, 6H), 6.13-6.01 (t, 2H), 4.15 (s, 3H); as shown in FIG. 2, H on the phenolic hydroxyl group in the structural formula does not show a peak on the hydrogen spectrum due to the comparative living wave.
IR(KBr,cm -1 ) selected bands 3451.2,3057.0,1608.6,1584.5,1486.1,1437.3,1329.7,1291.1,1273.1,1227.5,1165.1,1133.2,1110.2,987.7,821.2,752.7,693.8; as shown in fig. 3.
ESI-MS:429.2014([M-I] + ) The method comprises the steps of carrying out a first treatment on the surface of the As shown in fig. 4.
The compound L prepared in this example was first prepared to 10 by dissolving in a dimethyl sulfoxide solvent -3 50 mu L of mother solution is absorbed and respectively dispersed in 0%,10%,20%,30%,40%,50%,60%,70%,80%,90% and 99% of water/glycerol viscous medium with different volume fractions, and the total volume of each system is 5mL, so that the final concentration of the compound L is 10 mu M, and the fluorescence emission spectrum is tested under the excitation wavelength of 514nm; as a result, as shown in fig. 5A, it can be seen from the graph that the fluorescence intensity of the compound L gradually increases as the viscosity of the medium increases.
The compound L prepared in this example was first prepared to 10 by dissolving in a dimethyl sulfoxide solvent -3 mu.L of mother liquor was pipetted into the mol/L mother liquor and dispersed in PBS buffer solution containing amino acid, BSA, DNA and RNA, 99% glycerol, respectivelyIn the solution and PBS buffer solution, the total volume of each system is 5mL, the final concentration of the compound L in each system is 10 mu M, the final concentration of the amino acid, BSA, DNA and RNA is 200 mu M, the fluorescence emission spectrum is tested under 514nm excitation wavelength, and the dispersion medium is taken as the abscissa, I/I 0 Plotted on the ordinate, wherein I is the fluorescence intensity value at 646nm, I, of compound L after interaction with different analytes 0 Fluorescence intensity values at 646nm for PBS buffer solution of compound L; as a result, as shown in fig. 5B, it can be seen from the figure that compound L exhibits strong fluorescence only in the viscous medium, and that the fluorescence emission of compound L in the viscous medium can be free from interference by other analytes.
Example 2
Lysosome targeting fluorescent probe for lysosome targeting research
Human hepatoma cells (HepG 2 cells) were seeded on laser confocal dishes (NEST cat# 80002) 10 per well 6 The cells can be used when the cell density rises to 60%. Compound L prepared in example 1 was formulated with dimethyl sulfoxide solvent to give a compound of formula 10 -2 The mother liquor of mol/L was diluted to 8. Mu.M with medium, 1mL of the mother liquor was added to cultured human hepatoma cells (HepG 2 cells) in each dish, and the mixture was diluted with medium containing 95% air and 5% CO 2 The reaction is carried out for 20 minutes at 37 ℃ in a gaseous incubator, PBS buffer solution is used for washing for 2 times, and then the result is observed on a Leica TCS SP8 laser confocal microscope device, and the excitation wavelength is set to be 514nm; as shown in fig. 6, it can be seen from the figure that compound L is able to target lysosomal sites within cells.
To demonstrate that the probes of the present invention target lysosomes, four groups of human hepatoma cells (HepG 2 cells) were each loaded with 8. Mu.M Compound L in 95% air and 5% CO as described above 2 The reaction is carried out for 20 minutes at 37 ℃ in a gas incubator, the reaction is washed by PBS buffer solution for 2 times, then laser copolymerization is carried out for Jiao Xianying under the excitation wavelength of 514nm, and the development result is shown as A1-A4 in FIG. 6;
then co-incubating with commercial dyes Lysotracker green, mitotracker green, hoechst 33342 and LCS LipidTOX Deep Red, respectively, for 20 min, washing with PBS buffer solution for 2 times, performing laser copolymerization Jiao Xianying at excitation wavelengths of 488nm, 405nm and 633nm, respectively, and developing the results shown in FIG. 6B 1-B4; FIGS. C1-C4 correspond to the superposition results of FIGS. A1-A4 and FIGS. B1-B4, respectively; figures D1-D4 correspond to pearson coefficient values for co-localization results, respectively. From fig. 6, it can be demonstrated that compound L is able to target lysosomes within cells.
Example 3
Lysosomal targeting fluorescent probes to monitor changes in lysosomal viscosity
In order to further study the change of the fluorescence intensity of the lysosome targeting fluorescent probe after the influence of external environmental stimulus on the in-vivo viscosity of the lysosome, the embodiment selects dexamethasone which can be used as an immunosuppressant of a cell lysosome membrane, and the medicament can induce the enhancement of the lysosome viscosity. Two groups of human hepatoma cells (HepG 2 cells) were each purified with 8. Mu.M Compound L in the presence of 95% air and 5% CO as in example 2 2 Allowing to act at 37deg.C for 20 min in a gas incubator, washing with PBS buffer solution for 2 times, adding fresh culture medium, taking one group of human liver cancer cells, adding 5 μm dexamethasone, and mixing with 95% air and 5% CO 2 Allowing the mixture to act in a gas incubator at 37 ℃ for 30 minutes, and then performing laser copolymerization Jiao Xianying at an excitation wavelength of 514nm, wherein the excitation wavelength is set to be 514nm; as shown in FIG. 7, it can be seen from the graph that the fluorescence intensity of the probe is obviously enhanced after the cells are stimulated by dexamethasone, which shows that the change of the viscosity in the lysosome can induce the spatial configuration of the probe L to change, thereby displaying bright red fluorescence.
Example 4
Lysosome targeting fluorescent probes track the process of lysosome fusion and migration
Human hepatoma cells (HepG 2 cells) were combined with 8. Mu.M Compound L in the presence of 95% air and 5% CO as in example 2 2 The gas incubator is acted for 20 minutes at 37 ℃, after washing for 2 times by PBS buffer solution, fresh culture medium is added, and 5 mu M chloroquine solution is added, the chloroquine is acted to induce the movement of lysosomes under the condition that cells keep healthy,in the presence of 95% air and 5% CO 2 Allowing the mixture to act in a gas incubator at 37 ℃ for 30 minutes, and then performing laser copolymerization Jiao Xianying at an excitation wavelength of 514nm, wherein the excitation wavelength is set to be 514nm; as shown in FIG. 8, it can be seen that probe L can monitor the process of lysosomal fusion and migration in real time.
The foregoing detailed description of a lysosomal targeting fluorescent probe, and methods of making and using the same, with reference to the examples, is illustrative and not limiting, and several examples can be enumerated in the limited scope, therefore, variations and modifications within the spirit and scope of the present invention should be considered within the scope of the present invention.
Claims (9)
1. The lysosome targeting fluorescent probe is characterized by having a structural formula as follows:
2. the method for preparing the lysosomal targeting fluorescent probe according to claim 1, wherein the preparation method comprises the following steps: dissolving a compound M1 and a compound M2 in an organic solvent, carrying out reflux reaction by taking organic base as a catalyst, cooling to room temperature after the reaction is finished, and carrying out suction filtration, washing and drying to obtain the lysosome targeted fluorescent probe;
the structural formula of the compound M1 is as follows:
the structural formula of the compound M2 is as follows:
the organic base is piperidine.
3. The method according to claim 2, wherein the organic solvent is ethanol.
4. The preparation method according to claim 2, wherein the ratio of the amounts of the substances of the compound M1, the compound M2 and the catalyst is 1:1.1 to 1.2:0.6 to 0.7.
5. The method according to claim 2, wherein the concentration of the compound M1 with respect to the organic solvent is 0.05 to 0.1M.
6. The method according to claim 2, wherein the time of the reflux reaction is 22 to 26 hours.
7. Use of a lysosomal targeting fluorescent probe according to claim 1 for lysosomal labelling or monitoring lysosomal viscosity changes for non-disease diagnosis or treatment purposes.
8. Use of a lysosomal targeting fluorescent probe according to claim 1 for real-time monitoring of lysosomal fusion and migration processes for non-disease diagnosis or treatment purposes.
9. A method of lysosomal labeling for non-disease diagnosis or treatment purposes using the lysosomal targeting fluorescent probe according to claim 1, comprising the steps of: biological cells were incubated with the lysosome targeted fluorescent probes for 20 minutes and developed using a laser confocal microscope.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011547009.6A CN112645874B (en) | 2020-12-24 | 2020-12-24 | Lysosome targeting fluorescent probe and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011547009.6A CN112645874B (en) | 2020-12-24 | 2020-12-24 | Lysosome targeting fluorescent probe and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112645874A CN112645874A (en) | 2021-04-13 |
| CN112645874B true CN112645874B (en) | 2023-05-23 |
Family
ID=75359859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011547009.6A Active CN112645874B (en) | 2020-12-24 | 2020-12-24 | Lysosome targeting fluorescent probe and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112645874B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114989081B (en) * | 2022-05-10 | 2023-06-13 | 南华大学 | Colorimetric probe and preparation method and application thereof |
| CN114957082B (en) * | 2022-06-22 | 2024-03-26 | 苏州优逸兰迪生物科技有限公司 | Lysosome targeting fluorescent probe and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848509A (en) * | 2020-08-13 | 2020-10-30 | 江西科技师范大学 | Molecular rotor type red light mitochondrial probe and preparation method and application thereof |
-
2020
- 2020-12-24 CN CN202011547009.6A patent/CN112645874B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848509A (en) * | 2020-08-13 | 2020-10-30 | 江西科技师范大学 | Molecular rotor type red light mitochondrial probe and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Ming-Qi Wang等.A triphenylamine-based colorimetric and fluorescent probe with donor–bridge–acceptor structure for detection of G-quadruplex DNA.Bioorganic & Medicinal Chemistry Letters.2015,第25卷scheme 1. * |
| 溶酶体荧光探针研究新进展;李美含等;有机化学;第37卷;全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112645874A (en) | 2021-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112645874B (en) | Lysosome targeting fluorescent probe and preparation method and application thereof | |
| CN103160274A (en) | Fluorescence probe for detecting intracellular hydrogen sulfide and preparation method and application of fluorescence probe | |
| CN101012207B (en) | Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use | |
| CN103896928A (en) | pH fluorescent chemical sensor as well as synthetic method and application thereof | |
| CN112500386A (en) | Near-infrared HClO fluorescent probe based on pyrrazone oxime, and preparation and application thereof | |
| CN108219780A (en) | A kind of near infrared fluorescent probe and its preparation method and application | |
| CN112745258B (en) | Mitochondrial fluorescent probe with high signal-to-noise ratio and preparation method and application thereof | |
| CN111533730B (en) | Washing-free cell membrane targeted fluorescent probe and preparation method and application thereof | |
| CN106634964B (en) | Oxazine compound is preparing the application near infrared fluorescent probe | |
| CN110776458B (en) | Fluorescent probe for detecting mitochondrial membrane potential and preparation method and application thereof | |
| CN110357896B (en) | Compound, preparation and application thereof in detecting divalent copper ions and strong acid pH | |
| CN110372681B (en) | Application of self-assembled nano fluorescent probe for selectively detecting human serum albumin | |
| CN115650897A (en) | Fluorescent probe for simultaneously detecting Cys and mitochondrial viscosity and preparation method and application thereof | |
| CN108840818B (en) | Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide | |
| CN114644598B (en) | Dihydro phenazine derivative and use thereof | |
| CN113773292B (en) | Washing-free AIEgen fluorescent probe targeting lipid droplets and preparation method and application thereof | |
| CN113651759B (en) | Detection of Fe in organism 2+ Two-photon fluorescent probe and preparation method and application thereof | |
| CN114507204B (en) | Golgi apparatus targeted superoxide anion fluorescent probe, preparation method and application thereof | |
| JP6321634B2 (en) | Optical second harmonic generation compound, optical second harmonic generation dye composition, and cell inspection method | |
| CN111635350B (en) | PCPC and application thereof in preparation of antitumor drugs | |
| CN110272434B (en) | High-sensitivity acid-base probe, preparation and biological detection application thereof | |
| CN116003381A (en) | Mitochondrion targeting two-photon fluorescent probe with double-salt structure, and preparation method and application thereof | |
| CN115745969B (en) | Fluorescent probe, preparation method and application thereof | |
| KR101350077B1 (en) | Novel 3-indolinone derivatives and a composition comprising same | |
| WO2022027174A1 (en) | Cell nucleus fluorescent dye and dyeing method therefor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |