CN111233928A - Coumarin derivative Mito-Cys and preparation method and application thereof - Google Patents
Coumarin derivative Mito-Cys and preparation method and application thereof Download PDFInfo
- Publication number
- CN111233928A CN111233928A CN202010140601.8A CN202010140601A CN111233928A CN 111233928 A CN111233928 A CN 111233928A CN 202010140601 A CN202010140601 A CN 202010140601A CN 111233928 A CN111233928 A CN 111233928A
- Authority
- CN
- China
- Prior art keywords
- cys
- mito
- coumarin derivative
- preparing
- diethylamino
- 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.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- 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"
-
- 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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
- G01N21/6458—Fluorescence microscopy
-
- 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
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention provides a coumarin derivative Mito-Cys and a preparation method and application thereof, wherein the coumarin derivative is named as (E) - (3- (4- (3- (7- (diethylamino) -2-oxo-2H-benzopyran-3-yl) -3-oxoprop-1-en-1-yl) -2-methoxyphenoxy) -3-oxopropyl) triphenyl phosphonium salt in the Chinese, and is named as (E) - (3- (4- (3- (7- (diethylamino) -2-oxo-2H-chromen-3-yl) -3-oxoprop-1-en-1-yl) -2-methoxyphenoxy) -3-oxopropyl) triphenylphosphonium in the English, abbreviated as Mito-Cys. The invention provides a method for specifically detecting cysteine, which is based on a coumarin derivative Mito-Cys and detects cysteine in a phosphate buffer solution (pH 8.0). The Mito-Cys can carry out semi-quantitative detection on cysteine in cell mitochondria, and has wide application prospect in the field of biomolecule detection.
Description
Technical Field
The invention relates to a fluorescence detection reagent, and particularly belongs to a coumarin derivative Mito-Cys, a preparation method thereof, and application of the derivative Mito-Cys in cell mitochondrial cysteine detection.
Background
Biological thiols are one of the major reducing substances in cells, and as a center of sulfur metabolism in cells, cysteine (Cys) plays a critical role in the synthesis of glutathione, the neurotransmitter taurine, the gas signaling molecule hydrogen sulfide, and various proteins. Cys acts as a first-line antioxidant in the cell, and abnormalities in its concentration are closely linked to oxidative stress. Intracellular mitochondria are the energy mill of the cell, and their aerobic metabolic processes are the main source of reactive oxygen species in the cell. While an imbalance in the level of redox in the cell is a direct factor leading to oxidative stress. The deep knowledge of the redox process in the mitochondria of cells will promote the breakthrough progress of the research of a series of serious diseases induced by oxidative stress. Therefore, the method has important practical significance for detecting the concentration of Cys in the cell mitochondria.
The invention provides a coumarin derivative Mito-Cys and a preparation method thereof, and realizes the specific detection of Cys of cell mitochondria based on the derivative Mito-Cys.
Disclosure of Invention
The invention aims to provide a coumarin derivative and a preparation method thereof, and the coumarin derivative can be used as a detection reagent for Cys fluorescence detection; the selectivity and the sensitivity are high when Cys is detected; the derivative can be used for semi-quantitative detection of Cys in cell mitochondria.
The invention provides a coumarin derivative, wherein the name of the coumarin derivative is (E) - (3- (4- (3- (7- (diethylamino) -2-oxo-2H-benzopyran-3-yl) -3-oxoprop-1-en-1-yl) -2-methoxyphenoxy) -3-oxypropyl) triphenyl phosphonium quaternary salt, the name of the coumarin derivative is (E) - (3- (4- (3- (7- (diethyl imine) -2-oxo-2H-chromen-3-yl) -3-oxoprop-1-en-1-yl) -2-methoxyphenoxy) -3-oxopropoxy) triphenylphosphonium, and the abbreviation of the coumarin derivative is Mito-Cys. The structural formula is as follows:
the coumarin derivative shows excellent sensitivity and selectivity to Cys in a phosphate buffer solution (pH 8.0), and the detection process is simple, convenient and sensitive.
Preparation of Mito-Cys:
1) 3-acetyl-7-N, N-diethylamino coumarin and 4-hydroxy-3-methoxybenzaldehyde are mixed according to a molar ratio of 1: 1.2 dissolving in ethanol, adding a catalytic amount of piperidine, and refluxing until the reaction is complete; the solvent is evaporated to dryness under reduced pressure to obtain a crude product, and then the crude product is subjected to column chromatography (eluent is ethyl acetate, petroleum ether and the ratio of 1: 3 in volume) to obtain (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-ketone;
2) mixing the (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-one and 2-carboxyethyl (triphenyl phosphonium salt) obtained in the step 1) according to a molar ratio of 1: 1 is dissolved in dichloromethane, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1 equivalent) and 4-dimethylaminopyridine (0.2 equivalent) are added, and the mixture is stirred at room temperature until the reaction is completed; the system was evaporated to dryness under reduced pressure and then separated by column chromatography (eluent methanol: dichloromethane: 1: 20 by volume ratio) to obtain the target compound Mito-Cys.
The application of the coumarin derivative Mito-Cys of the invention comprises the following steps: the derivative can be used for specifically detecting cysteine in water environment and cell mitochondria in a pH 8.0 system; the detection comprises fluorescence detection and cell imaging detection.
Compared with the prior art, the invention has the following beneficial effects:
1. the coumarin derivative Mito-Cys is simple to synthesize, low in cost and easy for large-scale production;
2. the detection method can realize the specificity detection of Cys, and other amino acids do not react with Mito-Cys;
3. the detection method realizes the semi-quantitative detection of Cys specificity in the cell mitochondria;
4. the detection method is simple and can be realized only by means of a fluorescence spectrophotometer and a laser confocal microscope.
Description of the drawings:
FIG. 1 shows the Mito-Cys hydrogen spectrum of coumarin derivative.
FIG. 2Mito-Cys carbon spectra characterization of coumarin derivatives.
FIG. 3 mass spectrum characterization of the coumarin derivative Mito-Cys.
FIG. 4 is a graph of fluorescence emission intensity over time for example 2 of the effect of Mito-Cys with Cys.
FIG. 5 graph comparing fluorescence emission intensity of example 3Mito-Cys with various analytes. Wherein, 1, Gly; glu; met; 4, Ser; asp; tyr; his; lys; 9, Trp; asn; hcy; GSH; cys, 13.
FIG. 6 example 4 specific semi-quantitative detection of endogenous Cys by Mito-Cys in HeLa cells. Wherein, 1, PBS; 2.100 μ MCys; 3.200 μ MCys; 4.2 mMGSH; 5.2mMGSHEe the fluorescence intensity of the cells at 498nm after incubation, respectively.
FIG. 7 example 5 imaging of Mito-Cys vs. intracellular Cys and imaging of the co-localization of the commercial dye mitochondrial Red. Wherein a) green channel (Mito-Cys) is imaged; b) red channel (mitochondrial red) imaging; c) three-channel superposition of green, red and bright fields; d) correlation of red channel and green channel fluorescence signals.
The specific implementation mode is as follows:
the present invention is further illustrated by the following examples and figures, but the scope of the present invention is not limited by the following examples.
Example 1
Preparation and characterization of Mito-Cys:
dissolving 3-acetyl-7-N, N-diethylamino coumarin (2mmol, 0.52g) and 4-hydroxy-3-methoxybenzaldehyde (2.4mmol, 0.36g) in ethanol, adding 3-5 drops of piperidine, and refluxing for 20h until the reaction is complete; the solvent is evaporated to dryness under reduced pressure to obtain a crude product, and then the crude product is subjected to column chromatography (eluent is ethyl acetate, petroleum ether and the ratio of 1: 3 in volume) to obtain (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-ketone;
dissolving (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-one (1mmol, 0.39g) and 2-carboxyethyl (triphenyl phosphonium salt) (1mmol, 0.41g) in dichloromethane, adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1mmol, 0.19g) and 4-dimethylaminopyridine (0.2mmol, 0.024g), and stirring at room temperature for 20H until the reaction is complete; the system was evaporated to dryness under reduced pressure and then separated by column chromatography (eluent methanol: dichloromethane: 1: 20 by volume ratio) to obtain the target compound Mito-Cys.
1H NMR (600MHz, DMSO) δ 8.60(s, 1H), 7.94-7.79 (m, 16H), 7.68(t, J ═ 13.6Hz, 2H), 7.48(s, 1H), 7.36(d, J ═ 8.1Hz, 1H), 7.14(d, J ═ 7.9Hz, 1H), 6.82(d, J ═ 8.8Hz, 1H), 6.61(s, 1H), 4.06-3.91 (m, 2H), 3.80(s, 3H), 3.51(dd, J ═ 13.3, 6.8Hz, 4H), 2.99(dd, J ═ 15.5, 8.8Hz, 2H), 1.15(t, J ═ 6.5Hz, 6H) (fig. 1).13C NMR (151MHz, DMSO) δ 186.1, 160.4, 158.7, 153.5, 151.4, 148.9, 141.7, 140.8, 135.6, 134.7, 134.3, 134.3, 132.9, 130.8, 130.7, 126.1, 123.7, 121.0, 118.6, 118.0, 115.9, 113.5, 110.8, 108.4, 96.4, 56.4, 44.9, 27.0, 12.8 (fig. 2). HR-MS [ probe]+Theoretical m/z 710.2666, found 710.2692 (FIG. 3).
Example 2
Preparing a phosphate buffer solution with the pH of 8.0, preparing a DMSO solution of 2mM Mimo-Cys, and preparing an aqueous solution of 20mM Cys; 2mL of phosphate buffered solution (pH 8.0), 10. mu.L of Mito-Cys in DMSO was added to a fluorescence cuvette, and 20. mu.L of Cys in water was added and detected over time on a fluorescence spectrophotometer (414nm excitation). The fluorescence intensity at 498nm gradually increased within 0-7min, and the fluorescence emission diagram is shown in FIG. 4.
Example 3
Preparing a phosphate buffer solution with the pH of 8.0, preparing a DMSO solution of 2mM Mimo-Cys, and respectively preparing aqueous solutions of 20mM Cys, Hcy, Asn, Asp, Glu, Gly, His, Lys, Met, Ser, Trp, Tyr and 100mM GSH; in 13 fluorescence cuvettes, 2mL of each phosphate buffer solution (pH 8.0) and 10. mu.L of Mito-Cys in DMSO were added, and 20. mu.L of each aqueous solution of LCys, Hcy, Asn, Asp, Glu, Gly, His, Lys, Met, Ser, Trp, Tyr and GSH was added. After 10min the respective fluorescence intensity (414nm excitation) was detected on a fluorescence spectrophotometer (see FIG. 5). Cys causes a significant increase in the fluorescence intensity of the detection system at 498nm, while other analytes do not cause a significant change in the fluorescence intensity of the detection system. Experiments prove that other analytes do not interfere with the detection of Cys by a system.
Example 4
Preparing a DMSO solution of 2mM Mimo-Cys, preparing aqueous solutions of 20mM Cys, 200mM GSH and 200mM GSHEe respectively, numbering 96-well enzyme-labeled plates (5 multiplied by 6) which are cultured with HeLa cells, and adding 1.PBS respectively; 2.100 μ MCys; 3.200 μ MCys; 4.2 mMGSH; a solution of 5.2mM GSHEe (final concentration) was incubated at 37 ℃ for 1 h. After extensive washing with PBS, cells were incubated for 20min with a final concentration of 5. mu. MMito-Cys in PBS, and the fluorescence intensity at 498nm (414nm excitation) was measured in each well in a microplate reader (see FIG. 6). The fluorescence intensity of the cells of the pre-incubation groups of 100 mu MCys and 200 mu MCys is obviously increased and is in positive correlation with the concentration of the incubation Cys, and the fluorescence intensity of the cell pre-incubation group of 2mMGSHEe (cell membrane permeable GSH donor) is close to that of the control group. This experiment demonstrates that Mito-Cys can be specifically semi-quantitatively detected at the cellular level for Cys.
Example 5
Preparing a DMSO solution of 2mM Mimo-Cys, and preparing a 0.2 mu M commercialized PBS solution of mitochondrial red dye-mitochondrial red; HeLa cell-grown dishes were incubated sequentially with 5. mu. MMito-Cys-final concentration of PBS (10min) and 0.2. mu.M-final concentration of commercial mitochondrial red dye-mitochondrial red PBS (15min) and imaged with confocal laser microscopy (see FIG. 7). 405nm and 561nm are respectively used as the exciting light of a green channel (480-520nm) and a red channel (580-620nm), the green channel and the red channel both have strong fluorescence emission and the correlation of fluorescence signals is high, and the Pearson coefficient is 0.82. This experiment demonstrates that Mito-Cys can detect Cys in mitochondria.
Claims (8)
1. A coumarin derivative Mito-Cys is characterized in that the structural formula is as follows:
2. the method for preparing the coumarin derivative Mito-Cys according to claim 1, comprising the steps of:
1) dissolving 3-acetyl-7-N, N-diethylamino coumarin and 4-hydroxy-3-methoxybenzaldehyde in ethanol, adding a catalytic amount of piperidine, and refluxing until the reaction is complete; the solvent is evaporated to dryness under reduced pressure to obtain a crude product, and then the crude product is separated by column chromatography to obtain (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-ketone;
2) dissolving the (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-one and 2-carboxyethyl (triphenyl quaternary phosphonium salt) obtained in the step 1) in dichloromethane, adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 4-dimethylaminopyridine, and stirring at room temperature until the reaction is completed; and (4) carrying out column chromatography separation after the system is decompressed and evaporated to dryness to obtain the target compound Mito-Cys.
3. The method for preparing the coumarin derivative Mito-Cys according to claim 2, wherein the molar ratio of 3-acetyl-7-N, N-diethylaminocoumarin to 4-hydroxy-3-methoxybenzaldehyde in step 1) is 1: 1.2.
4. the method for preparing the coumarin derivative Mito-Cys according to claim 2, wherein the eluent in the column chromatography in step 1) is ethyl acetate: petroleum ether is 1: 3.
5. the method for preparing the coumarin derivative Mito-Cys according to claim 2, wherein in step 2) (E) -7- (diethylamino) -3- (3- (4-hydroxy-3-methoxyphenyl) acryloyl) -2H-benzopyran-2-one, 2-carboxyethyl (triphenylphosphonium), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, and 4-dimethylaminopyridine are present in a molar ratio of 1: 1: 1: 0.2.
6. the method for preparing the coumarin derivative Mito-Cys according to claim 2, wherein the eluent in the column chromatography in step 2) comprises methanol: 1-dichloromethane: 20.
7. the use of the coumarin derivative Mito-Cys according to claim 1 in the detection of cysteine in an aqueous environment at pH 8.0.
8. The use of the coumarin derivative Mito-Cys of claim 1 in the preparation of a test agent for the detection of mitochondrial cysteine in animal cells.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010140601.8A CN111233928B (en) | 2020-03-03 | 2020-03-03 | Coumarin derivative Mito-Cys and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010140601.8A CN111233928B (en) | 2020-03-03 | 2020-03-03 | Coumarin derivative Mito-Cys and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111233928A true CN111233928A (en) | 2020-06-05 |
| CN111233928B CN111233928B (en) | 2021-07-02 |
Family
ID=70863370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010140601.8A Active CN111233928B (en) | 2020-03-03 | 2020-03-03 | Coumarin derivative Mito-Cys and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111233928B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079858A (en) * | 2020-09-24 | 2020-12-15 | 山西大学 | Coumarin derivative Th-HM1, and synthetic method and application thereof |
| CN112939918A (en) * | 2021-02-05 | 2021-06-11 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016025382A2 (en) * | 2014-08-09 | 2016-02-18 | Baylor College Of Medicine | Probes for quantitative imaging of thiols in various environments |
| US20180306792A1 (en) * | 2017-04-18 | 2018-10-25 | Amrita Vishwa Vidyapeetham | Flourescent exomarker probes for hydrogen sulfide detection |
-
2020
- 2020-03-03 CN CN202010140601.8A patent/CN111233928B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016025382A2 (en) * | 2014-08-09 | 2016-02-18 | Baylor College Of Medicine | Probes for quantitative imaging of thiols in various environments |
| US20180306792A1 (en) * | 2017-04-18 | 2018-10-25 | Amrita Vishwa Vidyapeetham | Flourescent exomarker probes for hydrogen sulfide detection |
Non-Patent Citations (1)
| Title |
|---|
| 岳永康: ""半胱氨酸荧光探针的设计及生物成像应用"", 《中国博士学位论文全文数据库 基础科学辑》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079858A (en) * | 2020-09-24 | 2020-12-15 | 山西大学 | Coumarin derivative Th-HM1, and synthetic method and application thereof |
| CN112079858B (en) * | 2020-09-24 | 2021-09-28 | 山西大学 | Coumarin derivative Th-HM1, and synthetic method and application thereof |
| CN112939918A (en) * | 2021-02-05 | 2021-06-11 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
| CN112939918B (en) * | 2021-02-05 | 2022-07-19 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111233928B (en) | 2021-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108484622B (en) | Synthesis of multi-signal fluorescent probe and application thereof in simultaneous differential detection of Hcy, Cys and GSH | |
| Kang et al. | A novel ratiometric fluorescent H2S probe based on tandem nucleophilic substitution/cyclization reaction and its bioimaging | |
| Chen et al. | A tri-site fluorescent probe for simultaneous sensing of hydrogen sulfide and glutathione and its bioimaging applications | |
| Peng et al. | A novel fluorescent probe for selective detection of hydrogen sulfide in living cells | |
| CN107973787B (en) | Coumarin derivative DMAC (Dimethylacetamide) and preparation method and application thereof | |
| CN110156688B (en) | Fluorescent probe for detecting polarity of targeted endoplasmic reticulum and application thereof | |
| CN107602502B (en) | ESIPT type fluorescent probe for biological mercaptan detection and application | |
| Yang et al. | A novel mitochondria-targeted ratiometric fluorescent probe for endogenous sulfur dioxide derivatives as a cancer-detecting tool | |
| CN109867611B (en) | Water-soluble two-photon hydrogen sulfide fluorescent probe for detecting red wine and hydrogen sulfide in vivo and preparation method and application thereof | |
| CN113121520B (en) | Fluorescent dye and fluorescent probe with AIE + ESIPT + ICT mechanism, and preparation method and application thereof | |
| CN111233928B (en) | Coumarin derivative Mito-Cys and preparation method and application thereof | |
| Hou et al. | A colorimetric and red emissive fluorescent probe for cysteine and its application in bioimaging | |
| CN113185506B (en) | Synthesis of multi-signal fluorescent probe and application thereof in detection of Cys, GSH and Hcy | |
| CN111718319A (en) | Fluorescent probe for distinguishing and detecting mercaptan and monitoring Cys/GSH metabolism and preparation method thereof | |
| CN110257055B (en) | High-selectivity glutathione ratio detection type fluorescent probe, and synthesis method and application thereof | |
| CN110642857B (en) | Difunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof | |
| CN110894193B (en) | Synthesis of novel fluorescent probe and application of novel fluorescent probe in cysteine detection | |
| CN113637048A (en) | Two-photon fluorescent probe of gamma-glutamyl transpeptidase, and preparation method and application thereof | |
| CN111153893A (en) | For detecting SO in cell mitochondria2Derivative ratiometric fluorescent probes and uses thereof | |
| CN114736255B (en) | Fluorescent probe for detecting flavone derivative of beta-galactosidase, preparation method and application thereof, kit and use method thereof | |
| CN114106024B (en) | Fluorescent probe and preparation method and application thereof | |
| CN111087362B (en) | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof | |
| CN105418560B (en) | Long wavelength's hydrazine colorimetric fluorescence probe and preparation method thereof | |
| CN111187289B (en) | Hydrogen peroxide fluorescent probe and preparation method and application thereof | |
| CN110229203B (en) | Hexosamine fluorescent probe and preparation method and application thereof |
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 |