CN111825692B - Hydrogen polysulfide fluorescent probe and preparation method and application thereof - Google Patents
Hydrogen polysulfide fluorescent probe and preparation method and application thereof Download PDFInfo
- Publication number
- CN111825692B CN111825692B CN202010739792.XA CN202010739792A CN111825692B CN 111825692 B CN111825692 B CN 111825692B CN 202010739792 A CN202010739792 A CN 202010739792A CN 111825692 B CN111825692 B CN 111825692B
- Authority
- CN
- China
- Prior art keywords
- hydrogen polysulfide
- fluorescent probe
- polysulfide
- hydrogen
- probe
- 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
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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 fluorescent probes, and particularly relates to a hydrogen polysulfide fluorescent probe as well as a preparation method and application thereof. The preparation method of the hydrogen polysulfide fluorescent probe comprises the following steps: 1) condensing 2-mercaptoacetic acid or 2-mercaptopropionic acid with trityl alcohol to obtain an intermediate; 2) reacting the intermediate obtained in the step 1) with fluorescein to obtain the hydrogen polysulfide fluorescent probe. The hydrogen polysulfide fluorescent probe is used for detecting hydrogen polysulfide, and has high selectivity, high sensitivity and H detection2SnThe concentration is convenient and fast.
Description
Technical Field
The invention belongs to the technical field of fluorescent probes, and particularly relates to a hydrogen polysulfide fluorescent probe as well as a preparation method and application thereof.
Background
Active sulfur species (RSS) are key biological signal molecules in a class of organisms for the regulation of cellular activity, including hydrogen sulfide (H)2S), thiol (RSH), hydrogen polysulfide (H)2Sn,n>1) And the like. Has wide pathophysiological action in nervous system and cardiovascular system, and has close relationship with nerve conduction, vasodilation, blood pressure regulation, mitochondrial protection, apoptosis and the like. In vivo, hydrogen sulfide (H)2S) Signal pathway is associated with posttranslational modification of cysteine residues to form cysteine oversulfides, the signaling of which may be by hydrogen polysulfide (H)2Sn,n>1) And H2And S is realized together. Recent research found H2SnCan activate transient receptor potential protein (TRPA1) channel to regulate intracellular calcium ion concentration, and promote Nrf2 to nucleus by releasing nuclear factor E2-related factor (Nrf2) from hydrated Kelch-like epichlorohydrin-related protein-1 (Keap1)Transport, regulate the activity of PTEN. Endogenous H2SnThe synthesis may be mediated by enzymes in the organism, such as cystathionine beta-synthase and cystathionine gamma-lyase. Recent studies have also found that 3-mercaptopyruvate phosphotransferase is capable of producing H from 3-mercaptopyruvate in the brain2SnAnd modulate the activity of ion channels and protein kinases. Thus, development was made on H2SnThe novel method for accurately detecting the concentration is significant for deeply understanding the related physiological functions. For H in complex biological samples2SnThe accurate detection of the concentration is often limited by various factors, so that the detection result is not ideal. Conventional H2SnThe concentration detection methods include mass spectrometry, ultraviolet spectrometry, and the like, but these methods are limited by long detection time, low sensitivity, and inability to detect in situ in a living body. The fluorescent probe analysis method has the advantages of simplicity, convenience, rapidness, high sensitivity, good selectivity, low cost and the like, so that the fluorescent probe is utilized to realize H2SnThe accurate detection becomes the target pursued by scientific researchers. However, H has been developed2SnFluorescent probes still have the following disadvantages: one is that the probe is easily consumed by biological thiols, e.g. H with 2-fluoro-5-nitrobenzyl ester as the recognition group2SnThe fluorine atom in the molecular structure of the series of fluorescent probes is easily subjected to nucleophilic substitution by the sulfhydryl group of biological thiol to cause probe consumption; secondly, the selectivity in a complex system is poor; and thirdly, the sensitivity is not high. In view of the above, a method for rapidly detecting H with high selectivity, high sensitivity and convenience is developed2SnThe technique of concentration is very important.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a hydrogen polysulfide fluorescent probe and a preparation method and application thereof.
The technical scheme provided by the invention is as follows:
a hydrogen polysulfide fluorescent probe has the following structural general formula:
The inventor finds that the selectivity of the fluorescent probe for hydrogen polysulfide can be remarkably improved by introducing triphenyl alkyl into the molecular structure of the fluorescent probe for hydrogen polysulfide to regulate and control the steric hindrance.
Specifically, the preparation method of the hydrogen polysulfide fluorescent probe comprises the following steps:
1) condensing 2-mercaptoacetic acid or 2-mercaptopropionic acid with trityl alcohol to obtain an intermediate;
2) reacting the intermediate obtained in the step 1) with fluorescein to obtain the hydrogen polysulfide fluorescent probe;
wherein the structural formula of the intermediate is as follows:
According to the technical scheme, the hydrogen polysulfide fluorescent probe can be obtained by synthesizing a short-circuit line through condensation of carboxyl of the intermediate and hydroxyl of a fluorescein closed-loop structure.
Specifically, the synthetic route is as follows:
specifically, in step 1):
the molar use ratio of the 2-mercaptoacetic acid or the 2-mercaptopropionic acid to the trityl alcohol is 25 (20-30);
the solvent is the mixture of chloroform and trifluoroacetic acid, or dichloromethane is also added;
the reaction temperature is 0-30 ℃;
the reaction time is 1.5-2.5 h;
the reaction environment is an anhydrous protective gas environment.
Specifically, in the step 2):
the molar use ratio of the intermediate to the fluorescein is (2-3) to 1;
the solvent is 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, 4-dimethylaminopyridine and dichloromethane, or trichloromethane is also added;
the reaction temperature is 0-30 ℃;
the reaction time is 4-6 h;
the reaction environment is a protective gas environment.
The invention also provides application of the hydrogen polysulfide fluorescent probe to detecting hydrogen polysulfide.
The detection method has high selectivity and high sensitivity, and can detect H2SnThe concentration is convenient and fast.
Drawings
FIG. 1 shows the fluorescence titration of the fluorescent probe TrtS3-FL for detecting hydrogen polysulfide.
FIG. 2 shows the response time of the fluorescent probe TrtS3-FL to hydrogen polysulfide.
FIG. 3 shows the selectivity of the fluorescent probe TrtS3-FL for hydrogen polysulfide.
FIG. 4 is a fluorescent image of intracellular hydrogen polysulfide with the fluorescent probe TrtS 3-FL.
FIG. 5 is a fluorescent image of intracellular hydrogen polysulfide with the fluorescent probe TrtS 3-FL.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1: synthesis of TrtS2-FL
The compound 2-mercaptoacetic acid (2.30g,25mmol) and the compound trityl alcohol (6.5g,25mmol) were dissolved in chloroform (30ml) under anhydrous argon atmosphere, trifluoroacetic acid (5ml) was slowly added over 5 minutes, and after 2 hours at room temperature, the solvent was removed under reduced pressure and dichloromethane-n-hexane was recrystallized to give intermediate TrtS 2. Intermediate TrtS2(0.835g,2.5mmol), fluorescein (0.332g,1mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (0.479g,2.5mmol), 4-dimethylaminopyridine (0.122g,1mmol) and dichloromethane (10ml) were reacted under argon protection and magnetic stirring at room temperature for 5 hours, the solvent was removed under reduced pressure, and column chromatography was performed using dichloromethane as an eluent to give TrtS2-FL as a white solid in 30% yield.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3):δ8.02(d,J＝7.4Hz,1H),7.66(t,J＝7.3Hz,1H),7.62(t,J＝7.4Hz,1H),7.45(d,J＝7.8Hz,12H),7.30(t,J＝7.5Hz,12H),7.25-7.21(m,6H),7.14(d,J＝7.4Hz,1H),6.97(s,2H),6.77(d,J＝8.7Hz,2H),6.68(d,J＝8.7Hz,2H),3.21(s,4H)；13C NMR(100MHz,CDCl3):δ169.0,167.5,152.8,151.8,151.4,143.8,135.2,130.0,129.5,128.8,128.1,127.0,126.0,125.2,124.0,117.4,116.5,110.1,81.5,67.6,34.6；
mass spectrometry characterization data: HRMS Calcd for C62H44O7S2[M+H]+965.2607,found965.2600.
Example 2: synthesis of TrtS3-FL
The compound 2-mercaptopropionic acid (2.65g,25mmol) and the compound trityl alcohol (6.5g,25mmol) were dissolved in chloroform (30ml) under an anhydrous argon atmosphere, and trifluoroacetic acid (5ml) was slowly added over 5 minutes to react at room temperature for 2 hours, after which the solvent was removed under reduced pressure and dichloromethane-n-hexane was recrystallized to give intermediate TrtS 3. Intermediate TrtS3(1.74g,5mmol), fluorescein (0.664g,2mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (0.958g,5mmol), 4-dimethylaminopyridine (0.244g,2mmol) and dichloromethane (20ml) were reacted under magnetic stirring under argon atmosphere at room temperature for 5 hours, the solvent was removed under reduced pressure and column chromatography was performed using dichloromethane as eluent to give TrtS3-FL as a white solid in 82% yield.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3):δ8.01(d,J＝7.5Hz,1H),7.66(t,J＝7.4Hz,1H),7.61(t,J＝7.3Hz,1H),7.44(d,J＝7.7Hz,12H),7.28(t,J＝7.6Hz,12H),7.24-7.19(m,6H),7.15(d,J＝7.4Hz,1H),7.04(d,J＝2.1Hz,2H),6.81-6.74(m,4H),2.56(t,J＝7.1Hz,4H),2.44(t,J＝7.1Hz,4H)；13C NMR(100MHz,CDCl3):δ169.7,169.0,152.9,151.8,151.4,144.4,135.2,130.0,129.5,128.8,127.9,126.7,126.0,125.1,123.9,117.6,116.4,110.2,81.5,66.9,33.6,26.7；
mass spectrometry characterization data: HRMS Calcd for C64H48O7S2[M+H]+993.2920,found993.2901.
Example 3: fluorescence titration of hydrogen polysulfide was detected with the fluorescent probe TrtS 3-FL.
As shown in FIG. 1, a fluorescent probe TrtS3-FL (10. mu.M) was added to a phosphate buffer solution (pH 7.4) containing 100. mu.M of cetyltrimethylammonium bromide at 37 ℃. When hydrogen polysulfide of different concentrations is added into the probe solution, the fluorescence intensity of the probe is gradually increased. The fluorescence intensity of the probe at 514nm and the concentration of hydrogen polysulfide (0-50 mu M) show good linear relation (R)20.997), from which a detection limit of 185nM can be calculated. This example demonstrates that probe TrtS3-FL is capable of highly sensitive detection of hydrogen polysulfide.
Example 4: the response time of the fluorescent probe TrtS3-FL to hydrogen polysulfide.
As shown in FIG. 2, at 37 ℃ the fluorescence probe TrtS3-FL (10. mu.M) was added to a phosphate buffer solution (pH 7.4) containing 100. mu.M of cetyltrimethylammonium bromide, and hydrogen polysulfide (100. mu.M) was added thereto, and the change in fluorescence intensity at 514nm with time was recorded, and it was found that the fluorescence intensity of TrtS3-FL was almost saturated at 20 minutes. This example demonstrates that probe TrtS3-FL can rapidly detect hydrogen polysulfide. The time of the bottom-up curves in the graph increases in sequence.
Example 5: and (3) selective experiment of a fluorescent probe TrtS3-FL for hydrogen polysulfide.
As shown in fig. 3, in each group of phosphate buffer solutions (pH 7.4) containing 100 μ M of cetyltrimethylammonium bromide, the fluorescent probe TrtS3-FL (10 μ M) was added at 37 ℃, and then the different physiologically active sulfur interferents were added: cysteine (200. mu.M), glutathione (1mM), homocysteine (100. mu.M), sodium sulfide (100. mu.M), dimethyltrithiol (200. mu.M), reduced glutathione (100. mu.M), sodium thiosulfate (100. mu.M), sodium sulfite (100. mu.M), sodium thiosulfate (100. mu.M), sodium sulfate (100. mu.M). This example demonstrates that probe TrtS3-FL is highly selective for hydrogen polysulfide, only hydrogen polysulfide causing a significant increase in the fluorescence intensity of the probe at 514nm, while other physiologically active sulfur species are hardly changed.
Example 6: fluorescence imaging of intracellular hydrogen polysulfide by the fluorescent probe TrtS 3-FL.
As shown in fig. 4, human lung adenocarcinoma cells a549 were selected to verify the ability of probe trs 3-FL to image exogenous/endogenous hydrogen polysulfide at the cellular level. The cell imaging experiments were divided into three groups: 1. a control group, wherein the probe TrtS3-FL and A549 cells are incubated for 1 hour at 37 ℃; 2. in the exogenous hydrogen polysulfide cell imaging experiment, at 37 ℃, hydrogen polysulfide and A549 cells are incubated for 2 hours, and then a probe TrtS3-FL is added for incubation for 1 hour; 3. endogenous hydrogen polysulfide cell imaging experiments were performed by first treating cells with Lipopolysaccharide (LPS) for 12 hours, followed by 1 hour incubation with probe TrtS 3-FL. The results show that fluorescence was enhanced to a different extent compared to the control, whether exogenous addition of hydrogen polysulfide or endogenous hydrogen polysulfide production was stimulated by LPS. This example demonstrates the ability of probe TrtS3-FL to image endogenous/exogenous hydrogen polysulfide at the cellular level.
Example 7: fluorescence imaging of hydrogen polysulfide in zebra fish is performed by a fluorescent probe TrtS 3-FL.
As shown in fig. 5, zebrafish was selected to verify the ability of probe trs 3-FL to image exogenous/endogenous hydrogen polysulfide at the living level. In vivo imaging experiments were divided into three groups: 1. a control group, wherein the probe TrtS3-FL is incubated with zebrafish for 1 hour at 37 ℃; 2. in an exogenous hydrogen polysulfide in-vivo imaging experiment, at 37 ℃, firstly, incubating hydrogen polysulfide and zebra fish for 2 hours, and then, adding a probe TrtS3-FL for co-incubation for 1 hour; 3. in the endogenous hydrogen polysulfide in-vivo imaging experiment, zebrafish are treated by Lipopolysaccharide (LPS) for 12 hours and then incubated by a probe TrtS3-FL for 1 hour. The results show that fluorescence was enhanced to a different extent compared to the control, whether exogenous addition of hydrogen polysulfide or endogenous hydrogen polysulfide production was stimulated by LPS. This example demonstrates the ability of probe TrtS3-FL to image endogenous/exogenous hydrogen polysulfide at the living level.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (5)
1. A hydrogen polysulfide fluorescent probe is characterized in that the structural general formula is as follows:
2. A method for preparing a hydrogen polysulfide fluorescent probe according to claim 1, comprising the steps of:
1) condensing 2-mercaptoacetic acid and trityl alcohol to obtain an intermediate;
2) reacting the intermediate obtained in the step 1) with fluorescein to obtain the hydrogen polysulfide fluorescent probe;
wherein the structural formula of the intermediate is as follows:
3. The method for preparing a hydrogen polysulfide fluorescent probe of claim 2, wherein in step 1):
the molar use ratio of the 2-mercaptoacetic acid to the trityl alcohol is 25 (20-30);
the solvent is the mixture of chloroform and trifluoroacetic acid;
the reaction temperature is 0-30 ℃;
the reaction time is 1.5-2.5 h;
the reaction environment is an anhydrous protective gas environment.
4. The method for preparing a hydrogen polysulfide fluorescent probe of claim 2, wherein in step 2):
the molar use ratio of the intermediate to the fluorescein is (2-3) to 1;
the solvent is the mixture of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, 4-dimethylaminopyridine and dichloromethane;
the reaction temperature is 0-30 ℃;
the reaction time is 4-6 h;
the reaction environment is a protective gas environment.
5. The application of the hydrogen polysulfide fluorescent probe in preparing the hydrogen polysulfide fluorescent probe reagent is characterized in that the structural general formula of the hydrogen polysulfide fluorescent probe is as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010739792.XA CN111825692B (en) | 2020-07-28 | 2020-07-28 | Hydrogen polysulfide fluorescent probe and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010739792.XA CN111825692B (en) | 2020-07-28 | 2020-07-28 | Hydrogen polysulfide fluorescent probe and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111825692A CN111825692A (en) | 2020-10-27 |
| CN111825692B true CN111825692B (en) | 2021-10-26 |
Family
ID=72920268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010739792.XA Active CN111825692B (en) | 2020-07-28 | 2020-07-28 | Hydrogen polysulfide fluorescent probe and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111825692B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022084531A (en) * | 2020-11-26 | 2022-06-07 | キヤノン株式会社 | Novel compound and structural body for detecting hydrogen sulfide |
| CN113234039B (en) * | 2021-03-25 | 2022-04-29 | 徐州医科大学 | Hydrogen polysulfide fluorescent probe and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974169A (en) * | 2014-04-09 | 2015-10-14 | 中国科学院大连化学物理研究所 | Fluorescein H2S fluorescent probe as well as preparation and application thereof |
| CN107501221A (en) * | 2017-09-05 | 2017-12-22 | 中国科学院合肥物质科学研究院 | It is a kind of to fluorescence probe of hydrogen sulfide quick response and its production and use in organism |
-
2020
- 2020-07-28 CN CN202010739792.XA patent/CN111825692B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974169A (en) * | 2014-04-09 | 2015-10-14 | 中国科学院大连化学物理研究所 | Fluorescein H2S fluorescent probe as well as preparation and application thereof |
| CN107501221A (en) * | 2017-09-05 | 2017-12-22 | 中国科学院合肥物质科学研究院 | It is a kind of to fluorescence probe of hydrogen sulfide quick response and its production and use in organism |
Non-Patent Citations (1)
| Title |
|---|
| Polymer chain editing: functionality "knock-in","knock-out" and replacement via cross metathesis reaction and thiol-Michael addition;Jie Ren,et al.,;《Polym. Chem.》;20200706;第11卷;第4807-4817页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111825692A (en) | 2020-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109836394B (en) | Near-infrared fluorescent probe for identifying hydrogen sulfide and preparation method and application thereof | |
| CN108997326B (en) | Thiol fluorescent probe and preparation method and application thereof | |
| CN111825692B (en) | Hydrogen polysulfide fluorescent probe and preparation method and application thereof | |
| CN111592504B (en) | Fluorescent probe for detecting butyrylcholine esterase activity and synthetic method and application thereof | |
| Peng et al. | A novel fluorescent probe for selective detection of hydrogen sulfide in living cells | |
| CN109336835B (en) | Fluorescent probe for detecting activity of myeloperoxidase and preparation method and application thereof | |
| CN109336815B (en) | Two-photon fluorescent probe for detecting hypochlorous acid in intracellular endoplasmic reticulum | |
| Yang et al. | A simple fluorescent probe with two different fluorescence signals for rapid sequence distinguishing of Cys/Hcy/GSH and intracellular imaging | |
| Fang et al. | An instantaneous fluorescent probe for detecting hydrogen sulfide in biological systems | |
| CN109180716B (en) | Multi-signal ratio type distinguishing detection H2O2And H2Design, synthesis and application of fluorescent probe of S | |
| CN111217798A (en) | Coumarin-quinoline derivative and synthesis method and application thereof | |
| CN112694471B (en) | Benzondolium-phenothiazine derivative, and preparation and application thereof | |
| KR101845926B1 (en) | compound for detecting reactive oxygen species using rearrangement of amin-thiol and Method for manufacturing thereof | |
| CN117164575A (en) | Single excitation detection ONOO - Near infrared ratio fluorescent probe of (2), preparation method and application thereof | |
| CN114736199B (en) | Methylene blue-based near-infrared fluorescent probe and synthetic method and application thereof | |
| CN109485627B (en) | Coumarin derivative, synthesis method thereof and application of coumarin derivative in detection of hydrogen sulfide | |
| CN113637048A (en) | Two-photon fluorescent probe of gamma-glutamyl transpeptidase, and preparation method and application thereof | |
| CN114106024B (en) | 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 | |
| CN114230494A (en) | Synthesis of large Stokes shift near-infrared fluorescent probe and application thereof in detecting hydrogen sulfide | |
| CN110563609B (en) | Preparation method and application of near-infrared fluorescent probe for detecting selenious acid roots | |
| CN109781678B (en) | Preparation and application of ratiometric fluorescent probe applied to intramitochondrial hypochlorous acid detection | |
| CN109134483B (en) | Hydrogen sulfide fluorescent probe and preparation method and application thereof | |
| CN108760697B (en) | BODIPY derivative BDP-N3And synthesis method and application thereof | |
| CN112110903A (en) | Quantitative differential detection of Cys, Hcy, GSH and H2Fluorescent probe of S 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 |