CN119264072A - Fluorescent probe for cell imaging and its synthesis method and application - Google Patents
Fluorescent probe for cell imaging and its synthesis method and application Download PDFInfo
- Publication number
- CN119264072A CN119264072A CN202411782828.7A CN202411782828A CN119264072A CN 119264072 A CN119264072 A CN 119264072A CN 202411782828 A CN202411782828 A CN 202411782828A CN 119264072 A CN119264072 A CN 119264072A
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- substituted
- group
- imaging
- formula
- 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.)
- Pending
Links
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a fluorescent probe for cell imaging, a synthesis method and application thereof, wherein the fluorescent probe is a compound with a structure shown in a formula (I), wherein R 1、R2、R3 groups are respectively and independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, X groups are O, S or NH, Y groups are O, S or N, Z groups are O, S or N, and Ar groups are substituted or unsubstituted aryl or heteroaryl. The fluorescent probe can target mitochondrial fluorescence imaging, and has potential application to imaging other organelles.
Description
Technical Field
The invention relates to the technical field of fluorescent labeling, in particular to a fluorescent probe for imaging cells, and a synthesis method and application thereof.
Background
As a subcellular organelle, mitochondria play a vital role in many cellular processes, such as metabolism and apoptosis. As an energy source plant for cells, mitochondria mainly supply ATP required for life through oxidative phosphorylation. Furthermore, the intrinsic pathway of apoptosis is mainly triggered by cytochrome C release activated caspase proteins, which are the result of changes in mitochondrial outer membrane permeability. Many disease pathologies associated with mitochondrial metabolic disorders have been discovered in the last decades, and mitochondria have also become a critical therapeutic target, just as many cellular activities are closely related to mitochondria. For example, inhibiting mitochondrial respiration may limit the energy supply to cancer cells. Therefore, the method has important significance for the localization and distribution of mitochondria in cells.
Fluorescent probes are a class of fluorescent molecules that exhibit characteristic fluorescence in the ultraviolet-visible-near infrared region, and whose fluorescent properties (excitation and emission wavelengths, intensities, lifetimes, polarizations, etc.) can sensitively change as the properties of the environment, such as polarity, refractive index, viscosity, etc., change. Fluorescent probes are typically composed of three parts, a fluorescent group, a recognition group, and a linking group. The fluorescent group and the recognition group are assembled into a probe through the connecting group, and the fluorescent signal change is realized by utilizing the specific reaction of the recognition group and the detected substance.
In recent years, fluorescent probes play a vital role in scientific research and industrial applications. The fluorescent probe can detect substances with extremely low concentration and simultaneously maintain high selectivity and specificity, so that the fluorescent probe can be used for researching the action mechanism inside cell molecules and developing novel molecular probes and biological imaging technologies. And provides accurate detection and analysis in pharmaceutical analysis, environmental analysis, and food safety detection. In short, the fluorescent probe is used as a high-efficiency analysis tool, plays an irreplaceable role in scientific research, and provides strong technical support in the industrial and medical fields.
Most of the currently commercialized mitochondrial targeting probes are lipophilic and cationic, and toxicity resulting from accumulation within the mitochondrial matrix is one of the most important drawbacks. The self-quenching phenomenon and spectrum overlap caused by the narrow Stokes shift limit the practical application of the fluorescent probe (such as rhodamine 123, JC-1, the Stokes shift of less than 30 nm).
In recent years, fluorescent probes for detecting various objects to be detected have been sequentially designed, and the types of fluorophores used are various, and among them, 2- (2' -hydroxyphenyl) benzothiazole has been receiving attention because of its strong photostability, large stokes shift, and high quantum yield. However, the existing 2-phenylbenzoxazoles have the disadvantages that the emission and absorption wavelength is short, the absorption and emission wavelength of unsubstituted 2-phenylbenzoxazoles is lower than 365nm, and the probe emitting at a short wavelength has a large damage to cells in cell imaging. In addition, most 2-phenylbenzoxazoles use Excited State Intramolecular Proton Transfer (ESIPT) process to display fluorescence, which has the defect that the ESIPT process in a proton solvent is easily influenced by a solute-solvent intermolecular hydrogen bond, and the proton transfer capability in an aqueous solution is weaker, so that the detection in living cells is not facilitated.
Therefore, the development of a class of small molecule fluorescent probes which can be simply synthesized to target mitochondria is of great significance.
Disclosure of Invention
The invention provides a fluorescent probe for imaging cells, a synthesis method and application thereof, and the fluorescent probe can target mitochondrial fluorescent imaging and also has potential application of imaging other organelles.
The technical scheme of the invention is as follows:
A fluorescent probe for imaging cells, said fluorescent probe being a compound of the structure of formula (I):
;
Wherein each R 1、R2、R3 group is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
the X group is O, S or NH;
y is O, S or N;
Z is O, S or N;
Ar is a substituted or unsubstituted aryl or heteroaryl group.
Preferably, each R 1、R2 group is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
r 3 is 。
Preferably, the X group is O;
y is N;
the Z group is O, S or N.
Preferably, the Ar group is selected from:
。
preferably, the fluorescent probe is a compound with a structure shown in a formula (I-1), a formula (I-2) or a formula (I-3):
。
the invention also provides application of the fluorescent probe in live cell mitochondrial fluorescence microscopy imaging.
The fluorescent probe is a compound with a structure shown in the formula (I-1), the excitation wavelength is 453 nm, and the emission wavelength is 524 nm.
The fluorescent probe is a compound with a structure shown in the formula (I-2), the excitation wavelength is 466 nm, and the emission wavelength is 616 nm.
The fluorescent probe is a compound with a structure shown in the formula (I-3), the excitation wavelength is 440 nm, and the emission wavelength is 495nm.
Compared with the prior art, the invention has the beneficial effects that:
the method can lead the absorption and emission wavelength of the original 2-phenylbenzoxazole to be obviously red-shifted.
The method has the advantages of simple and easily obtained raw materials, mild reaction conditions, wide substrate applicability and the like, and meets the requirement of developing green environment-friendly chemistry.
Compared with the traditional fluorescent dye (such as fluorescein, rhodamine and cyanine), the small molecular fluorescent probe has larger Stokes shift, and can obviously change the excited emission wavelength by selecting different aromatic ring methylamines, thereby having great significance for the small molecular fluorescent dye.
Drawings
FIG. 1 is a nuclear magnetic H spectrum of a fluorescent probe Dye-1 prepared in example 1 of the present invention;
FIG. 2 is a nuclear magnetic C-spectrum of the fluorescent probe Dye-1 prepared in example 1 of the present invention;
FIG. 3 is a nuclear magnetic H spectrum of fluorescent probe Dye-2 prepared in example 2 of the present invention;
FIG. 4 is a nuclear magnetic C-spectrum of fluorescent probe Dye-2 prepared in example 2 of the present invention;
FIG. 5 is a nuclear magnetic H spectrum of fluorescent probe Dye-3 prepared in example 3 of the present invention;
FIG. 6 is a nuclear magnetic C-spectrum of fluorescent probe Dye-3 prepared in example 3 of the present invention;
FIG. 7 is a graph showing the maximum absorption wavelength and the maximum emission wavelength of the fluorescent probe Dye-1 prepared in example 1 of the present invention;
FIG. 8 is a graph showing the maximum absorption wavelength and the maximum emission wavelength of the fluorescent probe Dye-2 prepared in example 2 of the present invention;
FIG. 9 is a graph showing the maximum absorption wavelength and the maximum emission wavelength of the fluorescent probe Dye-3 prepared in example 3 of the present invention;
FIG. 10 is a confocal spectrum of fluorescent probe Dye-1 to MDA-MB-231 cells prepared in example 1 of the present invention.
Detailed Description
The invention will be described in further detail below with reference to the drawings and examples, it being noted that the examples described below are intended to facilitate an understanding of the invention and are not intended to limit the invention in any way.
Example 1
S1 (0.2 mmol) and sodium periodate (1.0 mmol) were added to a 20 ml reaction flask equipped with a magnetic stirrer and dissolved in 3 mL water and 1 mL acetonitrile. After sufficient dissolution, S2-1 (1.0 mmol) was added, and if a viscous liquid was stained with wall, 2: 2 mL acetonitrile was added. The reaction was stirred at room temperature 3 h. After the completion of the reaction, stirring was stopped, extraction was performed with ethyl acetate, and after crude separation by column chromatography (petroleum ether: ethyl acetate=3:1), a preparative plate (dichloromethane: ethyl acetate=10:1) was separated to give Dye-1 (6 mg, 5%) as a pale yellow solid. The nuclear magnetic H-spectrum and the nuclear magnetic C-spectrum of Dye-1 are shown in FIG. 1 and FIG. 2, respectively.
1H NMR (400 MHz, Chloroform-d) δ 8.24 – 8.17 (m, 2H), 7.78 – 7.71 (m, 2H), 7.65 (d,J= 8.3 Hz, 2H), 7.55 (d,J= 8.1 Hz, 2H), 7.33 (s, 1H), 6.59 (s, 1H), 6.11 (s, 1H), 5.47 (d,J= 6.9 Hz, 1H), 4.56 (d,J= 5.1 Hz, 2H), 4.50 – 4.44 (m, 1H), 3.70 (s, 3H), 3.21 (d,J= 14.6 Hz, 1H), 3.04 (dd,J= 14.7, 9.2 Hz, 1H), 1.40 (s, 9H).
Example 2
S1 (0.2 mmol) and sodium periodate (0.8 mmol) were added to a 20ml reaction flask equipped with a magnetic stirrer and dissolved in 3mL water and 1mL acetonitrile. After sufficient dissolution, S2-2 (0.8 mmol) was added, and if a viscous liquid was stained with wall, 2: 2 mL acetonitrile was added. The reaction was stirred at room temperature 3 h. After the completion of the reaction, stirring was stopped, extraction was performed with ethyl acetate, and after crude separation by column chromatography (petroleum ether: ethyl acetate=3:1), a preparative plate (dichloromethane: ethyl acetate=10:1) was separated to give Dye-2 (15.4 mg, 11%) as a pale yellow solid. The nuclear magnetic H-spectrum and the nuclear magnetic C-spectrum of Dye-2 are shown in FIG. 3 and FIG. 4, respectively.
1H NMR (400 MHz, Chloroform-d) δ 8.27 – 8.20 (m, 2H), 7.93 – 7.87 (m, 2H), 7.86 – 7.77 (m, 6H), 7.64 – 7.44 (m, 8H), 7.35 (s, 1H), 6.70 (s, 1H), 5.94 (s, 1H), 5.47 (d,J= 6.9 Hz, 1H), 4.60 (d,J= 4.9 Hz, 2H), 4.54 (td,J= 7.4, 4.2 Hz, 1H), 3.70 (s, 3H), 3.24 (d,J= 14.6 Hz, 1H), 3.08 (dd,J= 14.7, 8.7 Hz, 1H), 1.41 (s, 9H).
Example 3
S1 (0.2 mmol) and sodium periodate (1.0 mmol) were added to a 20ml reaction flask equipped with a magnetic stirrer and dissolved in 3mL water and 1mL acetonitrile. After sufficient dissolution, S2-3 (1.0 mmol) was added, and if a viscous liquid was stained with wall, 2: 2 mL acetonitrile was added. The reaction was stirred at room temperature 3 h. After the completion of the reaction, stirring was stopped, extraction was performed with ethyl acetate, and after crude separation by column chromatography (petroleum ether: ethyl acetate=4:1), a preparative plate (dichloromethane: ethyl acetate=15:1) was separated to give Dye-3 (21.5 mg, 20%) as a pale yellow solid. The nuclear magnetic H-spectrum and the nuclear magnetic C-spectrum of Dye-3 are shown in FIG. 5 and FIG. 6, respectively.
1H NMR (400 MHz, Chloroform-d) δ 8.11 – 8.04 (m, 2H), 7.59 – 7.55 (m, 2H), 7.50 – 7.46 (m, 2H), 7.39 (d,J= 8.2 Hz, 2H), 7.29 (s, 1H), 6.64 (s, 1H), 5.70 (s, 1H), 5.44 (d,J= 7.0 Hz, 1H), 4.54 – 4.43 (m, 3H), 3.68 (s, 3H), 3.21 (s, 2H), 3.06 (s, 2H), 1.40 (s, 9H).
Performance testing
The excitation wavelength of Dye-1 detected by Hitachi F-4700 in solvent acetonitrile was 453 nm and the emission wavelength was 524 nm (as shown in FIG. 7). The excitation wavelength of Dye-2 detected in solvent acetonitrile was 466 nm and the emission wavelength was 616 nm (as shown in fig. 8). The excitation wavelength of Dye-3 detected in the solvent acetonitrile was 440 nm and the emission wavelength was 495 nm (as shown in FIG. 9). In addition to these three examples, different fluorescent probes of different wavelengths can be obtained using different aromatic methylamines. And respectively taking the emission wavelength as an abscissa and the fluorescence intensity as an ordinate to obtain a wavelength-fluorescence intensity correlation map.
The fluorescent probe Dye-1 was co-localized with a commercial organelle probe for MDA-MB-231 cells, comprising the steps of:
(1) Preparing a dimethyl sulfoxide solution (simply called a storage culture solution) with the concentration of a fluorescent probe Dye-1 of 200 mu M, and preparing a dimethyl sulfoxide solution with the concentration of a mitochondrial deep red fluorescent probe (Mito-TRACKER DEEP RED FM) of 200 mu M.
(2) Cell culture, in which recovered MDA-MB-231 cells are cultured in a medium containing 10% bovine embryo serum, 1% diabody, 89% DMEM and 24h in an environment of 37 ℃ and 5% CO 2, and MDA-MB-231 cells cultured in the medium in an amount of 24h are placed in a confocal dish, and 24h is continuously cultured in an environment of 37 ℃ and 5% CO 2 in an inoculation amount of 3×10 5 cells/mL with the medium containing 10% bovine embryo serum, 1% diabody and 89% DMEM for later use.
(3) Mito-TRACKER DEEP RED FM at 200. Mu.M was prepared by adding 2. Mu.L of the mixture to 1 mL medium to prepare 400 nM probe working solution, and incubating the cells 20min in an environment of 5% CO 2 at 37 ℃. The medium was discarded and washed 2-3 times with PBS. Then, 2. Mu.L of the stock culture solution of Dye-1 was added to 1 mL medium to prepare 400. Mu.M probe working solution, and the solution was further incubated at 37℃in 5% CO 2 for 1 further h, and the medium was discarded. And washing with PBS for 2-3 times. 1 mL medium was added and fluorescence imaging was performed under confocal microscopy. The commercial mitochondrial probe was a red channel with excitation wavelength 640 nm and collection wavelength 665 nm. Dye-1 probe is the green channel, excitation wavelength 405 nm, collection wavelength 524 nm.
The imaging of mitochondria in MDA-MB-231 cells by fluorescent probe is shown in FIG. 10 (a) showing Dye-1 imaging the mitochondria in MDA-MB-231 cells, (b) showing commercial dark red mitochondrial Dye imaging the mitochondria in MDA-MB-231 cells, and (c) showing superposition of the first two signal channels. This suggests that Dye-1 can precisely localize the mitochondria in the cell, and that the linear mitochondria in MDA-MB-231 cells are clearly visible.
The foregoing embodiments have described the technical solutions and advantages of the present invention in detail, and it should be understood that the foregoing embodiments are merely illustrative of the present invention and are not intended to limit the invention, and any modifications, additions, substitutions and the like that fall within the principles of the present invention should be included in the scope of the invention.
Claims (9)
1. A fluorescent probe for imaging cells, wherein the fluorescent probe is a compound with a structure shown in a formula (I):
;
Wherein each R 1、R2、R3 group is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
the X group is O, S or NH;
y is O, S or N;
Z is O, S or N;
Ar is a substituted or unsubstituted aryl or heteroaryl group.
2. The fluorescent probe for cell imaging of claim 1, wherein each R 1、R2 group is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
r 3 is 。
3. The fluorescent probe for imaging cells of claim 1, wherein the X group is O;
y is N;
the Z group is O, S or N.
4. The fluorescent probe for imaging cells of claim 1, wherein the Ar group is selected from the group consisting of:
。
5. The fluorescent probe for imaging a cell according to claim 1, wherein the fluorescent probe is a compound having a structure represented by formula (I-1), formula (I-2) or formula (I-3):
。
6. Use of a fluorescent probe according to any one of claims 1-5 in live intracellular mitochondrial fluorescence microscopy imaging.
7. The use according to claim 6, wherein the fluorescent probe is a compound of the structure represented by formula (I-1), the excitation wavelength is 453 nm, and the emission wavelength is 524 nm;
。
8. The use according to claim 6, wherein the fluorescent probe is a compound of the structure represented by formula (I-2), the excitation wavelength is 466 nm, and the emission wavelength is 616 nm;
。
9. The use according to claim 6, wherein the fluorescent probe is a compound of the structure represented by formula (I-3), the excitation wavelength is 440 nm, and the emission wavelength is 495 nm;
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202411782828.7A CN119264072A (en) | 2024-12-06 | 2024-12-06 | Fluorescent probe for cell imaging and its synthesis method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202411782828.7A CN119264072A (en) | 2024-12-06 | 2024-12-06 | Fluorescent probe for cell imaging and its synthesis method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN119264072A true CN119264072A (en) | 2025-01-07 |
Family
ID=94125301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202411782828.7A Pending CN119264072A (en) | 2024-12-06 | 2024-12-06 | Fluorescent probe for cell imaging and its synthesis method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN119264072A (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120122136A1 (en) * | 2010-11-16 | 2012-05-17 | Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. | Self-immolative probes for enzyme activity detection |
| WO2015020281A1 (en) * | 2013-08-06 | 2015-02-12 | 아주대학교산학협력단 | Variable color two-photon fluorescent probe for detecting hydrogen sulfate, method for manufacturing same, and method for quantitatively imaging in vivo hydrogen sulfate using same |
| KR20160139527A (en) * | 2015-05-28 | 2016-12-07 | 고려대학교 산학협력단 | Two photon probe compound for imaging mitochondria and lysosomes and composition comprising the same |
| US20190187144A1 (en) * | 2016-07-20 | 2019-06-20 | East China University Of Science And Technology | Fluorescent probe and preparation method and use thereof |
| US20200248069A1 (en) * | 2017-09-29 | 2020-08-06 | East China University Of Science And Technology | Fluorescent probe, preparation method therefor and use thereof |
| CN111825629A (en) * | 2020-08-12 | 2020-10-27 | 江西理工大学 | A kind of benzoxazole fluorescent probe and preparation method and application |
| CN112079771A (en) * | 2020-09-23 | 2020-12-15 | 华中科技大学 | Water-soluble red fluorescent mitochondrial targeting probe and application thereof |
| CN114729927A (en) * | 2019-11-12 | 2022-07-08 | 梨花女子大学校产学协力团 | Cell imaging composition and cellular material imaging method using the same |
| CN116655618A (en) * | 2014-08-29 | 2023-08-29 | Chdi基金会股份有限公司 | Probes for imaging huntingtin |
-
2024
- 2024-12-06 CN CN202411782828.7A patent/CN119264072A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120122136A1 (en) * | 2010-11-16 | 2012-05-17 | Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. | Self-immolative probes for enzyme activity detection |
| WO2015020281A1 (en) * | 2013-08-06 | 2015-02-12 | 아주대학교산학협력단 | Variable color two-photon fluorescent probe for detecting hydrogen sulfate, method for manufacturing same, and method for quantitatively imaging in vivo hydrogen sulfate using same |
| CN116655618A (en) * | 2014-08-29 | 2023-08-29 | Chdi基金会股份有限公司 | Probes for imaging huntingtin |
| KR20160139527A (en) * | 2015-05-28 | 2016-12-07 | 고려대학교 산학협력단 | Two photon probe compound for imaging mitochondria and lysosomes and composition comprising the same |
| US20190187144A1 (en) * | 2016-07-20 | 2019-06-20 | East China University Of Science And Technology | Fluorescent probe and preparation method and use thereof |
| US20200248069A1 (en) * | 2017-09-29 | 2020-08-06 | East China University Of Science And Technology | Fluorescent probe, preparation method therefor and use thereof |
| CN114729927A (en) * | 2019-11-12 | 2022-07-08 | 梨花女子大学校产学协力团 | Cell imaging composition and cellular material imaging method using the same |
| CN111825629A (en) * | 2020-08-12 | 2020-10-27 | 江西理工大学 | A kind of benzoxazole fluorescent probe and preparation method and application |
| CN112079771A (en) * | 2020-09-23 | 2020-12-15 | 华中科技大学 | Water-soluble red fluorescent mitochondrial targeting probe and application thereof |
Non-Patent Citations (6)
| Title |
|---|
| "A Mitochondrial-Targeted Two-Photon Probe for Zinc Ion", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》, vol. 133, 30 March 2011 (2011-03-30), pages 5698 * |
| CHANG SU LIM ET AL.: "Two-Photon Probes for Lysosomes and Mitochondria: Simultaneous Detection of Lysosomes and Mitochondria in Live Tissues by Dual-Color Two-Photon Microscopy Imaging", 《CHEM. ASIAN J.》, vol. 10, 9 June 2015 (2015-06-09), pages 2241 * |
| JUSTIN P. PENNINGTON ET AL.: "Selective Fluorogenic Derivatization with Isotopic Coding of Catechols and 2-Amino Phenols with Benzylamine: A Chemical Basis for the Relative Determination of 3-Hydroxy- tyrosine and 3-Nitro-tyrosine Peptides", 《CHROMATOGRAPHIA》, vol. 66, 9 October 2007 (2007-10-09), pages 649 - 659, XP037841456, DOI: 10.1365/s10337-007-0410-8 * |
| KAILASH RATHORE ET AL.: "Dual-color imaging of cytosolic and mitochondrial zinc ions in live tissues with two-photon fluorescent probes", 《ORGANIC & BIOMOLECULAR CHEMISTRY》, vol. 12, 25 March 2014 (2014-03-25), pages 3407 * |
| SUNG KEUN BAE ET AL.: "A Ratiometric Two-Photon Fluorescent Probe Reveals Reduction in Mitochondrial H2S Production in a Parkinson’s Disease Gene Knockout Astrocytes", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》, 7 June 2013 (2013-06-07), pages 4 * |
| 姜娜 等: "线粒体荧光探针最新研究进展", 《化工学报》, vol. 67, no. 01, 31 January 2016 (2016-01-31), pages 176 - 190 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108069902A (en) | The fluorescence probe of fat drips and its preparation and application in one kind mark and/or detection cell | |
| CN107098923A (en) | One class feux rouges targets fluorescent dye and preparation method thereof and purposes near infrared emission lysosome | |
| CN103382313B (en) | A kind of naphthalimide fluorescent dye and its preparation and application | |
| Jiao et al. | A highly selective and pH-tolerance fluorescent probe for Cu2+ based on a novel carbazole-rhodamine hybrid dye | |
| CN110229120B (en) | Long-wavelength fluorescent dye molecule and preparation method thereof | |
| CN112321527A (en) | Lipid drop targeted fluorescent probe and synthetic method and application thereof | |
| CN104744453B (en) | Semicyanines for the detection of mitochondrial polarity | |
| CN113999254A (en) | A kind of benzothiadiazolimidazole fluorescent dye and its synthesis method | |
| CN101149374A (en) | Fluorescent probe for detecting intracellular hydrogen ions, synthesis method and application | |
| CN106432312A (en) | Mitochondria target fluorescence probe, as well as preparation method and application thereof | |
| CN112010838B (en) | A Fluorescent Probe for Endoplasmic Reticulum Based on Naphthalimide-Indole Derivatives and Its Application | |
| CN110031436B (en) | A Silicone Fluorescent Probe for Detecting Lipid Droplets | |
| US20240353433A1 (en) | Amino-substituted chromenoquinoline-based fluorescent marker, and preparation and use thereof | |
| CN105399775A (en) | Preparation method and application of phosphorescence iridium complexes with mitochondrial targeting function | |
| CN108484479B (en) | A kind of carbazole-based two-photon fluorescent probe and its preparation method and use | |
| CN112980431B (en) | A kind of fluorescent material based on cyclotripolyphosphazene and its preparation method and application | |
| CN110256339B (en) | Organic fluorescent dye molecule and preparation method thereof | |
| CN119264072A (en) | Fluorescent probe for cell imaging and its synthesis method and application | |
| CN111333649B (en) | A kind of cell membrane fluorescent probe based on SNAP-tag technology and its preparation and application | |
| CN116283966B (en) | A novel [1,8]-naphthyridine derivative and its preparation method and application in organelle fluorescence imaging and organelle polarity detection | |
| CN115477654B (en) | Near-infrared rhodamine dye with large Stokes displacement and synthesis method thereof | |
| CN114702447B (en) | Naphthalimide derivative and preparation method and application thereof | |
| CN105348268A (en) | Substituted carbazole-indole sulfonate derivative, and preparation method therefor and use thereof | |
| CN109503550A (en) | 2- azepine aryl-6-substituted-amino quinazolinones and its preparation method and application | |
| CN110845361B (en) | Compounds based on excited state intramolecular proton transfer type and their preparation methods and applications |
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 |