CN109232379B - For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof - Google Patents
For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof Download PDFInfo
- Publication number
- CN109232379B CN109232379B CN201811079424.6A CN201811079424A CN109232379B CN 109232379 B CN109232379 B CN 109232379B CN 201811079424 A CN201811079424 A CN 201811079424A CN 109232379 B CN109232379 B CN 109232379B
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- detecting
- preparation
- carrying
- detection
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- 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
- C09K2211/1011—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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention belongs to the technical field of synthesis of fluorescent probes, and provides a method for detecting CN (CN) to solve the problems of high detection limit, poor light stability and the like of the existing fluorescent probes‑The enhanced fluorescent probe is 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone, and the preparation method comprises the following steps: dissolving 1-acetylpyrene and N-ethylcarbazole-3-formaldehyde in absolute ethyl alcohol, then adding sodium hydroxide, continuously stirring for 4 hours at room temperature, separating out yellow solid, and tracking reaction by TLC; and after the reaction is finished, carrying out suction filtration, carrying out v/v washing on absolute ethyl alcohol and water 1/1, and carrying out vacuum drying to obtain yellow powder. The fluorescent probe is directed to Cyanide (CN)‑) The detection is enhanced, the reaction is rapid, the selectivity and the sensitivity are high, and the detection can be used for detecting the cyanide in organisms by combining the laser confocal scanning microscopy.
Description
Technical Field
The invention belongs to the technical field of synthesis of fluorescent probes, and particularly relates to a method for detecting CN-The enhanced fluorescent probe and the preparation method and the biological application thereof are applied to the detection of cyanide in organisms.
Background
Cyanide is a well-known highly toxic substance and is very harmful to human health. The small amount of cyanide causes extremely fatal poisoning due to the fact that cyanide ions are precipitated in the human body after cyanide is absorbed by living cells through the gastrointestinal tract, skin or lung, and the respiration of the living cells is inhibited by the binding with ferric iron of oxidative cytochrome oxidase in the mitochondria of the cells. However, cyanide is still widely used in various fields such as gold mining, electroplating, metallurgy, synthetic fiber and resin industries. Therefore, it is necessary to develop a method for conveniently and rapidly detecting cyanide ions.
The fluorescence spectrum detection technology has the advantages of quick real-time response, high resolution, high sensitivity, simple and convenient operation and the like, so that the fluorescence spectrum detection technology is widely used for detecting CN-The fluorescent probe of (2) has been reported. These probes are mainly based on mechanisms such as nucleophilic addition, hydrogen bonding interaction, formation of cyanide complex, and the like. The method urgently needs to synthesize the CN for detecting the biological sample by using the fluorescent probe with simplicity, high sensitivity, good selectivity, low detection limit and good light stability-。
Disclosure of Invention
The invention provides a method for detecting CN (CN) to solve the problems of high detection limit, poor light stability and the like of the existing fluorescent probe-The enhanced fluorescent probe, the preparation method and the biological application thereof, wherein the enhanced fluorescent probe is the enhanced fluorescent probe and is used for CN in organisms-And (6) detecting and imaging. The probe has the advantages of high sensitivity, high selectivity, low detection limit, good light stability and the like. And successfully applied to intracellular CN-Detection of (3).
The invention is realized by the following technical scheme: for detecting CN-The enhanced fluorescent probe is 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone, and the chemical structural formula of the enhanced fluorescent probe is as follows:
preparing the detection CN-The method for enhancing the fluorescent probe comprises the steps of mixing 1-acetylpyrene serving as a starting material with N-ethyl carbazole-3-formaldehyde according to a molar ratio of 1:1, then adding NaOH, stirring at room temperature for reacting for 4 hours, and obtaining 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone.
The method comprises the following specific steps:
(1) 1-acetylpyrene and N-ethylcarbazole-3-formaldehyde are mixed according to a molar ratio of 1:1, dissolving in absolute ethyl alcohol, and stirring at room temperature until reactants are completely dissolved to form a light yellow solution;
(2) according to the molar ratio of sodium hydroxide to 1-acetylpyrene of 18: 1, adding sodium hydroxide, continuously stirring for 4 hours at normal temperature, separating out a large amount of yellow precipitates, tracking the reaction by TLC, and performing reaction by using ethyl acetate: a solution of petroleum ether =1:3 is used as a developing solvent;
(3) and after the reaction is finished, carrying out suction filtration, washing with absolute ethyl alcohol and water 1/1 by v/v, and carrying out vacuum drying to obtain a yellow powdery product, namely the fluorescent probe.
The invention also provides the enhanced fluorescent probe at CN-The use in a quantitative detection process. The fluorescent probe is in vivo CN-To the use of (1) in the detection of (3).
The fluorescent probe can be used for quantitatively detecting CN-The method comprises the following steps:
(1) preparing 1mM fluorescent probe stock solution by using DMSO (dimethyl sulfoxide);
(2) adding a 2.0 mL DMSO system and 20.0 muL fluorescent probe stock solution into a fluorescent cuvette, performing a titration experiment on a fluorescence spectrophotometer, and carrying out a titration experiment with CN-The fluorescence intensity at 488nm is enhanced;
(3) with CN-Concentration is plotted on the abscissa as fluorescence intensity I488Plotting a chart for ordinate to obtain CN-The linear regression equation of the working curve of the concentration is as follows: i is488 = 6.74*[ CN-] + 100.72，CN-The unit of concentration is 10-6 mol/L; linear correlation coefficient of R2 = 0.9903, the optimal linear response range is 0-20 μ M, and the detection Limit (LOD) is 0.79 μ M.
The synthetic route of the fluorescent probe is as follows:
。
time response experiments prove that the fluorescent probe has good light stability and is used for CN-The response time is short, and experiments prove that the common anion does not interfere the CN system-The measurement of (1). The fluorescent probe provided by the invention is combined with a fluorescent confocal microscope imaging technology to prove that the fluorescent probe can be used for detecting CN in cells-。
Compared with the existing fluorescent probe, the fluorescent probe synthesized by the inventionThe optical probe has the following advantages: the fluorescent probe provided by the invention has the advantages of simple synthesis steps, low cost and good light stability. The detection method is simple and can be realized only by means of a fluorescence spectrometer. Fluorescence pair CN-The response has the advantages of good selectivity, high sensitivity, low detection limit and the like, and is not interfered by common metal ions. The probe can be used for detecting cyanogen in cells.
Drawings
FIG. 1 shows example 2 fluorescent probes with CN- A varying ultraviolet absorption spectrum; FIG. 2 shows example 3 fluorescent probes with CN- A varied fluorescence titration plot; FIG. 3 shows example 3 fluorescent probe pairs CN- A responsive operating curve; FIG. 4 is the response of the fluorescent probe of example 4 to common anions; FIG. 5 is an image of mouse mononuclear macrophage (RAW 264.7) in example 5.
Detailed Description
Example 1: for detecting CN- The fluorescent probe is 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone, and the chemical structural formula is as follows:
。
preparation of the assay CN-The method for enhancing the fluorescent probe comprises the steps of taking 1-acetylpyrene as an initial raw material, adding N-ethyl carbazole-3-formaldehyde according to the molar ratio of 1:1, then adding a proper amount of NaOH, and stirring at room temperature for reaction to obtain 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone.
The method comprises the following specific steps:
in a dry 50mL single-neck flask, 0.2461g (1 mmol) of 1-acetylpyrene and 0.2231g (1 mmol) of N-ethylcarbazole-3-carbaldehyde were added, stirred with 15mL of anhydrous ethanol until completely dissolved as a pale yellow solution, 0.75g of NaOH was added, the reaction was stirred at room temperature for about 4 hours (a large amount of yellow precipitate precipitated), and followed by TLC (V tracing)Ethyl acetate：VPetroleum ether=1: 3) after the reaction is finished, performing suction filtration, washing a filter cake for three times by using absolute ethyl alcohol and water (1/1, v/v), and performing vacuum drying to obtain 0.1701g of a yellow product; the yield was 37.87%.
For fluorescent probes1H NMR characterization, results are as follows:
1H NMR (600 MHz, DMSO, δ/ppm) 8.67 (s, 1H), 8.58 (d, J = 9.3 Hz, 1H), 8.46 (s, 2H), 8.43 – 8.39 (m, 2H), 8.35 – 8.32 (m, 3H), 8.20 – 8.16 (m, 2H), 7.97 (d, J = 7.5 Hz, 1H), 7.81 (d, J = 15.8 Hz, 1H), 7.75 (d, J = 15.8 Hz, 1H), 7.65 – 7.70 (m, 2H), 7.50 (t, J = 7.7 Hz, 1H), 7.25 (t, J = 7.5 Hz, 1H), 4.49 (m, 2H), 1.33 (t, J = 7.1 Hz, 3H).
13C NMR (150 MHz, DMSO, δ/ppm) 195.42, 148.05, 141.68, 140.57, 134.75, 132.94, 131.22, 130.64, 129.43, 129.33, 128.88, 127.80, 127.33, 127.24, 126.84, 126.72, 126.41, 125.80, 125.00, 124.98, 124.65, 124.49, 124.14, 123.21, 122.86, 122.73, 121.20, 120.07, 110.17, 110.10, 37.68, 14.23.
example 2: preparing 1mM fluorescent probe stock solution by using DMSO (dimethyl sulfoxide); adding a 2.0 mL DMSO system and 20.0 muL fluorescent probe stock solution into a fluorescent cuvette, and performing CN (fluorescence spectroscopy) on a fluorescence spectrophotometer-Ultraviolet titration experiment, and record its ultraviolet absorption spectrum, the ultraviolet absorption spectrogram is shown in figure 1. As can be seen from FIG. 1, with CN-The increase in the amount decreased the absorption peak at 324nm, while the UV absorption at 398 nm increased and the fluorescence intensity at 488nm increased.
Example 3: fluorescent probe with CN-Varied fluorescence titration map
CN was performed by adding 20.0 μ L of fluorescent probe stock solution to a 2.0 mL system of DMSO-Fluorescence titration experiment, detected on a fluorescence spectrophotometer, the probe itself has an emission peak at 545nm, as shown in FIG. 2, with CN-The increase in (c) shows a new peak at 488nm and gradually increases. The instrument parameters are that the slit widths of the excitation wavelength and the emission wavelength are respectively 2.5 nm and 2.5 nm, the voltage is 600V, and the maximum excitation wavelength of the fluorescent probe solution is as follows: lambda [ alpha ]ex415 nm and a maximum emission wavelength λem545 nm. As shown in FIG. 3, with CN-Concentration is on the abscissa in orderFluorescence intensity I488Plotting a chart for ordinate to obtain CN- The linear regression equation of the working curve of the concentration is as follows: i is488 = 6.74*[ CN-] + 100.72，CN-The unit of concentration is 10-6 mol/L; linear correlation coefficient of R2 = 0.9903, the optimal linear response range is 0-20 μ M, and the detection Limit (LOD) is 0.79 μ M.
Example 4: response of fluorescent probes to common anions
Adding 20.0 muL of fluorescent probe stock solution into a 2.0 mL DMSO system, and respectively adding other anions (F)-、Cl-、Br-、I-、CO3 2-、NO3 -、SO4 2-、AcO-、SCN-、SO3 2-、S2O3 2-、S2-) Making the final concentration of the solution to be 100 mu M, and adding CN-The final concentration is made to be 100 mu M, the fluorescence spectra are respectively measured, and the corresponding fluorescence intensity I of different anions is drawn488nmIs shown in the figure. The test proves that the result is shown in figure 4, other anions do not interfere the system to CN-Detection of (3).
Example 5: imaging of mouse mononuclear macrophage (RAW 264.7)
RAW264.7 cells (mouse monocyte macrophage leukemia cells) were cultured in DMEM medium containing 10% Fetal Bovine Serum (FBS) and 1% antibiotics at 37 deg.C in 5% CO2Culturing in an incubator. It was placed in a petri dish and grown adherent for 24 hours prior to use. In the experiment, the culture solution in the two dishes was extracted and washed with PBS buffer solution with pH =7.40, and then the dishes were incubated with 2.0 ml PBS (pH 7.40) buffer solution containing 20.0 μ L of the probe (1 mM, dissolved in DMSO) for about 15min, and then extracted and washed three times with PBS buffer solution with pH = 7.40. 10.0 μ L (1X 10) was added to one of the culture dishes-2M）CN- The cells were incubated with 2.0 mL of PBS buffer solution with pH =7.4 for about 10min and 25min, and then extracted, followed by washing with PBS buffer solution with pH = 7.40. Finally, only the incubated probe and the incubated probeThe cells with the probes incubated with cyanide ions were placed in a petri dish and observed under a laser confocal microscope with 2.0 mL of PBS solution with pH = 7.40. The fixed excitation wavelength is 405nm, and the collection emission band is a yellow channel (525-660 nm). As shown in FIG. 5, it can be seen from FIG. 5 that when only the probe was added, the fluorescence was slightly yellow (A1-A3) in the cells, and CN was added-The yellow color increased after 10min incubation (B1-B3), and the yellow fluorescence increased when the incubation time increased to 25min (C1-C3).
Claims (6)
1. For detecting CN-The enhanced fluorescent probe of (1), characterized in that: the fluorescent probe is 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) acrylketone, and the chemical structural formula is as follows:
2. preparation of a composition for detecting CN according to claim 1-The method of (3), wherein: 1-acetylpyrene is used as an initial raw material and is mixed with N-ethyl carbazole-3-formaldehyde according to the molar ratio of 1:1, then NaOH is added, and the mixture is stirred and reacts for 4 hours at room temperature to obtain 1- (pyrene-1-yl) -3- (N-ethyl carbazole-3-yl) propenone.
3. The preparation according to claim 2 for detecting CN-The method of (3), wherein: the method comprises the following specific steps:
(1) dissolving 1-acetylpyrene and N-ethylcarbazole-3-formaldehyde in absolute ethyl alcohol, and stirring at room temperature until reactants are completely dissolved to form a light yellow solution;
(2) according to the molar ratio of sodium hydroxide to 1-acetylpyrene of 18: 1, adding sodium hydroxide, continuously stirring for 4 hours at normal temperature, separating out yellow precipitate, and tracking the reaction by TLC, wherein the volume ratio is ethyl acetate: a solution of petroleum ether =1:3 is used as a developing solvent;
(3) and after the reaction is finished, carrying out suction filtration, washing with absolute ethyl alcohol and water 1/1 by v/v, and carrying out vacuum drying to obtain a yellow powdery product, namely the fluorescent probe.
4. A method for detecting CN as claimed in claim 1-In the preparation of CN-The use of the reagent for quantitative determination of (1).
5. A method for detecting CN according to claim 4-In the preparation of CN-The use of the reagent for quantitative detection of (1), characterized in that: the fluorescent probe is in vivo CN-To the use of (1) in the detection of (3).
6. A method for detecting CN according to claim 4-In the preparation of CN-The use of the reagent for quantitative detection of (1), characterized in that: the fluorescent probe can be used for quantitatively detecting CN-The method comprises the following steps:
(1) preparing 1mM fluorescent probe stock solution by using DMSO (dimethyl sulfoxide);
(2) adding a 2.0 mL DMSO system and 20.0 muL fluorescent probe stock solution into a fluorescent cuvette, performing a titration experiment on a fluorescence spectrophotometer, and carrying out a titration experiment with CN-The fluorescence intensity at 488nm is enhanced;
(3) with CN-Concentration is plotted on the abscissa as fluorescence intensity I488Plotting a chart for ordinate to obtain CN-The linear regression equation of the working curve of the concentration is as follows: i is488 = 6.74*[ CN-] + 100.72，CN-The unit of concentration is 10-6 mol/L; linear correlation coefficient of R2 = 0.9903, the optimal linear response range is 0 mu M-20 mu M, and the detection limit LOD is 0.79 mu M.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811079424.6A CN109232379B (en) | 2018-09-17 | 2018-09-17 | For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811079424.6A CN109232379B (en) | 2018-09-17 | 2018-09-17 | For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109232379A CN109232379A (en) | 2019-01-18 |
| CN109232379B true CN109232379B (en) | 2022-01-28 |
Family
ID=65059412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811079424.6A Active CN109232379B (en) | 2018-09-17 | 2018-09-17 | For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109232379B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478221A (en) * | 2022-02-25 | 2022-05-13 | 西华师范大学 | Pyrene-based AIE fluorescent probe and preparation method and application thereof |
| CN117088845B (en) * | 2023-08-25 | 2024-08-09 | 浙江工业大学 | Chemiluminescent probe for detecting cyanide and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105092553A (en) * | 2015-09-16 | 2015-11-25 | 山西大学 | Ratio type fluorescence probe for determining CN<-> as well as preparation method and application thereof |
| CN105203512A (en) * | 2015-09-16 | 2015-12-30 | 山西大学 | Carbazole fluorescent probe and preparation method and application thereof |
-
2018
- 2018-09-17 CN CN201811079424.6A patent/CN109232379B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105092553A (en) * | 2015-09-16 | 2015-11-25 | 山西大学 | Ratio type fluorescence probe for determining CN<-> as well as preparation method and application thereof |
| CN105203512A (en) * | 2015-09-16 | 2015-12-30 | 山西大学 | Carbazole fluorescent probe and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 咔唑类荧光探针的合成及其性能研究;刘瑜红;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20170615(第6期);全文 * |
| 咔唑类荧光探针的合成及应用研究;李志清;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20180315(第3期);全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109232379A (en) | 2019-01-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108398409B (en) | Method for detecting hypochlorite by fluorescence ratio | |
| CN108047060B (en) | Pyrene derivative fluorescent probe molecule for identifying and detecting formaldehyde and preparation method and application thereof | |
| CN106279124B (en) | A kind of fluorescence probe and the preparation method and application thereof for detecting tyrosinase | |
| CN110092773B (en) | Xanthene derivative and preparation method and application thereof | |
| CN113045596B (en) | Peroxynitroso anion and viscosity dual-response type fluorescent probe and preparation and application thereof | |
| CN109232379B (en) | For detecting CN-Enhanced fluorescent probe and preparation method and biological application thereof | |
| CN114181204B (en) | Near infrared fluorescent probe for detecting viscosity and preparation and application thereof | |
| CN111205220B (en) | Fluorescent probe and preparation method and application thereof | |
| CN110878085B (en) | Rapid high-selectivity hypobromous acid fluorescent probe, preparation method and application | |
| CN113354627B (en) | Near-infrared fluorescent compound for detecting viscosity and preparation and application thereof | |
| CN112794857A (en) | Preparation and application of novel fluorescent probe for high-selectivity detection of ferrous ions | |
| CN112624960B (en) | NTR-1 response type fluorescent probe based on benzindole, preparation method and application | |
| CN110642857B (en) | Difunctional fluorescent probe for detecting viscosity and pH, and preparation and application thereof | |
| CN112457360B (en) | Liver-targeted peroxynitrite fluorescent probe, and preparation method and application thereof | |
| CN110950877B (en) | Double-detection fluorescent probe, preparation method and application thereof in detection of hydrogen sulfide and copper ions | |
| CN115594672A (en) | Methylene blue near-infrared fluorescent probe and preparation method and application thereof | |
| CN112159377B (en) | Near infrared emission and simultaneous identification H 2 S、HSO 3- Fluorescent probe of (2) and use thereof | |
| CN111087362B (en) | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof | |
| CN109134483B (en) | Hydrogen sulfide fluorescent probe and preparation method and application thereof | |
| CN108840818B (en) | Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide | |
| CN108383819B (en) | Cysteine fluorescent probe based on coumarin ketone aldehyde and preparation and application thereof | |
| CN113121541A (en) | Synthesis and application of fluorescent probe capable of distinguishing gold ions and palladium species simultaneously | |
| CN114507204B (en) | Golgi apparatus targeted superoxide anion fluorescent probe, preparation method and application thereof | |
| CN111233909B (en) | Reagent for detecting cyanide ions and synthetic method and application thereof | |
| CN113979996B (en) | Phthalimide fluorescent probe for detecting copper ions, preparation method and application thereof, and copper ion detection method |
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 |