CN109503515A - A kind of methylene blue derivatives object and its synthetic method and application - Google Patents
A kind of methylene blue derivatives object and its synthetic method and application Download PDFInfo
- Publication number
- CN109503515A CN109503515A CN201811364038.1A CN201811364038A CN109503515A CN 109503515 A CN109503515 A CN 109503515A CN 201811364038 A CN201811364038 A CN 201811364038A CN 109503515 A CN109503515 A CN 109503515A
- Authority
- CN
- China
- Prior art keywords
- solution
- added
- methylene blue
- molar equivalent
- fluorescence
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/30—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with acyl radicals attached to the ring nitrogen atom
-
- 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
- G01N21/6428—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
- C09K2211/1007—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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Pathology (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention provides a kind of methylene blue derivatives object and its synthetic method and applications, the methylene blue derivatives object is: 4-azidobenzyl-3,7-bis (dimethylamino) -10H-phenothiazine-10-carboxylate, Chinese is bis- (the dimethylamino) -10H- phenthazine -10- carboxylates (MB1) of 4- azido benzyl -3,7-.Detection method is to pass through sepectrophotofluorometer quantitative detection H using the methylene blue derivatives object as detection reagent2The content of S.The detection process high sensitivity, selectivity is good, detection process is easy, testing result is accurate.
Description
Technical field
The present invention relates to azido compounds and sulfurated hydrogen detection, and in particular to a kind of methylene blue derivatives object and its synthesis side
Method and the derivative are in H2Application in S detection.
Background technique
Hydrogen sulfide (H2S) be a kind of colourless gas for having rotten egg smell, be considered as a long time it is toxic, to environment
It is harmful.But in recent ten years, a large amount of research discovery hydrogen sulfide is being widely present in the mammalian body, and is played extremely
Important physiological action.Research shows that hydrogen sulfide is the third gas letter after nitric oxide (NO) and carbon monoxide (CO)
Number molecule has different physiological roles.The effect of hydrogen sulfide includes modulation blood pressure, alleviates ischemic damage and reperfusion damage, is played anti-
Inflammation effect, adjust Cellular Oxidation stress pressure, reduce metabolic rate etc..The exception of hydrogen sulfide levels is related to a variety of diseases, such as
Down syndrome and Alzheimer's disease and cardiovascular disease etc..Up to the present, many methods are used to detect body
Outer and internal vulcanization hydrogen radical concentration, such as: gas-chromatography, spectrophotometry, electrochemical assay, methylene blue laws and small molecule are glimmering
Light probe.Wherein, small-molecule fluorescent probe preparation is easy, is easy to modify, various structures, may be implemented to small point of intracellular reactive
Highly sensitive, highly selective, the quick and real-time detection of son, has been considered to be most promising detection technique.Especially near-infrared
Region photon has smaller radiation energy, can reduce damage of the light to cell and biological living sample, and the luminous energy in the region is worn
Thoroughly into deeper living tissue, the imaging analysis in living animal body is realized.In addition, the biomolecule in the wave-length coverage
Autofluorescence is weaker, can avoid biological context interference.Therefore, near-infrared fluorescent molecular probe obtains the pass of more people in recent years
Note.
In the present invention, bis- (the dimethylamino) -10H- phenthazine -10- carboxylates of 4- azido benzyl -3,7- have been synthesized
(MB1), pass through H2The variation of S reaction front and back fluorescence intensity, realizes H2The detection of S.
Summary of the invention
The object of the present invention is to provide a kind of methylene blue derivatives object and its synthetic method, the methylene blue derivatives object is closed
At simple, it can be used near infrared detection H2S, and easy to operate, selectivity height.
A kind of methylene blue derivatives object provided by the invention is bis- (the dimethylamino) -10H- phenos of 4- azido benzyl -3,7-
Thiazine -10- carboxylate (MB1), English name are 4-azidobenzyl-3,7-bis (dimethylamino) -10H-
Phenothiazine-10-carboxylate, structural formula are as follows:
The synthetic method of bis- (the dimethylamino) -10H- phenthazine -10- carboxylates (MB1) of 4- azido benzyl -3,7-, step
Suddenly are as follows:
(1) in N2Under protection, condition of ice bath, 1 molar equivalent 4- aminobenzene methanol is dissolved in 10% hydrochloric acid solution；It will
1-1.5 molar equivalent sodium nitrite is dissolved in water, and is added dropwise in previous solu in 30min；Then 1-1.5 moles is worked as
Amount sodium azide is added portionwise wherein, and mixture is stirred to react 2h；It is extracted with ethyl acetate and water washing, collected organic layer is used
Anhydrous sodium sulfate dries, filters, filtrate on a rotary evaporator after rotary evaporation yellow oily compound 4- triazobenzene first
Alcohol；
(2) by 1-1.2 molar equivalent 4- triazobenzene methanol, 1 molar equivalent 3, bis- (the dimethylamino) -10H- pheno thiophenes of 7-
Piperazine -10- phosgene, 2.9-3.1 molar equivalent sodium carbonate and 1 molar equivalent 4-dimethylaminopyridine are dissolved in methylene chloride,
N215h is stirred to react under protection, condition of ice bath；It removes solvent and crude product is subjected to silica gel chromatography, it is solid to obtain white
Bis- (the dimethylamino) -10H- phenthazine -10- carboxylates (MB1) of body 4- azido benzyl -3,7-.
A kind of near infrared detection H2The method of S, step are as follows:
(1), it prepares pH=7.4, the PBS buffer solution that concentration is 10mM, prepares the DMSO solution of the MB1 of 2mM, prepare
The Na of 6.5mM2The aqueous solution of S；
(2), the DMSO solution of the PBS buffer solution of 1mL pH 7.4,1mL DMSO solution and 5 μ L MB1 is added to ultraviolet
It in cuvette and fluorescence cuvette, detects on UV detector and Fluorescence spectrophotometer, adds with to test sample respectively
The fluorescence intensity of the increase of the angle of incidence, 687nm gradually increases；
(3), in addition the DMSO solution of 1mL pH 7.4 PBS buffer solution, 1mL DMSO solution and 5 μ L MB1 is added to
In 10 fluorescence cuvettes, the H that volume is 1,2,3,4,5,6,7,8,9,10 μ L is added respectively2S(65×10-4M) solution,
Corresponding intensity at 687nm is measured on Fluorescence spectrophotometer, with Na2The concentration of S solution is abscissa, is vertical with fluorescence intensity
Coordinate draws figure, obtains H2The working curve of S concentration；Equation of linear regression are as follows: the unit of y=7.7529c+115.9933, c is
μM；
(4) DMSO solution of the PBS buffer solution of 1mL pH 7.4,1mL DMSO solution and 5 μ L MB1 is added to completely
Fluorescence cuvette in, draw V μ L testing sample solution with microsyringe, be added in this fluorescence cuvette, in fluorescence point
It is detected on light photometer, the ratio measured is substituted into the equation of linear regression of step (3), obtains concentration c, sample to be tested CTo test sample=
2000μL×c×10-6/ V μ L, can acquire H2The concentration of S.
Compared with prior art, the invention has the advantages that and effect: 1, detection method of the invention, to H2S is shown
High selectivity；2, to H2S realizes near infrared detection.
Detailed description of the invention:
The nucleus magnetic hydrogen spectrum figure of methylene blue derivatives object MB1 prepared by Fig. 1 embodiment 1
The mass spectrogram of methylene blue derivatives object MB1 prepared by Fig. 2 embodiment 1
Fig. 3 methylene blue derivatives object MB1 and H2The UV absorption figure of S effect
Fig. 4 methylene blue derivatives object MB1 and H2The fluorescent emission figure of S effect
The fluorescence histogram of Fig. 5 methylene blue derivatives object MB1 and various analytes
Fig. 6 measures H with methylene blue derivatives object MB12The working curve of S
Fig. 7 measures H with methylene blue derivatives object MB12The living cells laser confocal imaging figure of S
Specific embodiment:
Embodiment 1
The synthesis and characterization of bis- (the dimethylamino) -10H- phenthazine -10- carboxylates (MB1) of 4- azido benzyl -3,7-.
(1) in N2It protects, 4- aminobenzene methanol (317.72mg, 2.58mmol) is dissolved in the salt of 8mL10% under condition of ice bath
In acid solution.By sodium nitrite (NaNO2, 211.4mg, 3.06mmol) and it is dissolved in 3.2mL water, it is added dropwise in 30min
In previous solu.Then by sodium azide (NaN3, 200.7mg, 3.08mmol) and it is added portionwise wherein, mixture is stirred to react
2h.It is washed with ethyl acetate (3 × 50mL) extraction and water (3 × 50mL), collected organic layer, with anhydrous sodium sulfate (Na2SO4) dry
It is dry, filtering, filtrate on a rotary evaporator after rotary evaporation yellow oily compound 4- triazobenzene methanol.
(2) by 4- triazobenzene methanol (70mg, 0.47mmol), 3,7- bis- (dimethylamino) -10H- phenthazine -10-
Phosgene (140.1mg, 0.40mmol), sodium carbonate (Na2CO3, 124.4mg, 1.17mmol) and 4-dimethylaminopyridine (DMAP,
50.7mg, 0.4mmol) it is dissolved in 20mL methylene chloride, in N2It protects, is stirred to react 15h under condition of ice bath.Removing solvent simultaneously will
Crude product carries out silica gel chromatography, obtains bis- (the dimethylamino) -10H- pheno thiophenes of white solid 4- azido benzyl -3,7-
Piperazine -10- carboxylate (MB1).
Embodiment 2
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the solution of 2mM MB1 with DMSO, prepare
The Na of 65mM2The aqueous solution of S；The DMSO solution of PBS (pH 7.4) solution of 1mL, 1mL DMSO solution and 5 μ L MB1 are added to
In ultraviolet cuvette and fluorescence cuvette, H is taken2The solution of S, is added in cuvette with microsyringe, respectively in ultraviolet spectrometry
It is detected on photometer and Fluorescence spectrophotometer, with S2-The increase of time is added, the fluorescence intensity of 687nm gradually increases.It is purple
Outer absorption figure and fluorescent emission figure, are shown in Fig. 3 and Fig. 4.
Embodiment 3
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the MB1 solution of 2mM with DMSO, prepare 65mM
Na2The aqueous solution of S；In 15 fluorescence cuvettes, each PBS (pH 7.4) solution, 1mL DMSO solution and 5 μ that 1mL is added
The DMSO solution of L MB1, then it is separately added into 5 μ L H2S and 5 μ L (2 × 10-1M various analytes): SO4 2-、S2O3 2-、
SCN-、Ca2+、Mg2+、K+、Na+、GSH、L-Me、L-Cys、L-Ala、L-Hcy、H2O2And HClO, it is examined on Fluorescence spectrophotometer
It surveys, draws the histogram of the fluorescence intensity at the corresponding 687nm of different analytes, (see Fig. 4).H2S makes at the 687nm of reagent
Fluorescence intensity obviously increases, and other analytes do not cause the variation of reagent fluorescence intensity substantially, sees Fig. 5.
The experiment proved that other analytes not interference system to H2The measurement of S.
Embodiment 4
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the MB1 solution of 2mM with DMSO, prepare
The Na of 6.5mM2The aqueous solution of S；The DMSO solution of PBS (pH 7.4) solution of 1mL, 1mL DMSO solution and 5 μ L MB1 are added
Into fluorescence cuvette, the Na that volume is 1,2,3,4,5,6,7,8,9,10 μ L is added respectively2S(65×10-4M) solution is molten
Liquid measures corresponding intensity at 687nm, on Fluorescence spectrophotometer with Na2The concentration of S solution is abscissa, strong with fluorescence
Degree is that ordinate draws figure, obtains H2The working curve of S concentration；Equation of linear regression are as follows: y=7.7529c+115.9933, c's
Unit be μM, see Fig. 6；
Embodiment 5
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the MB1 solution of 2mM with DMSO, use distilled water
Preparing SNP, (donor of business NO is used for stimulation of endogenous H2The generation of S) and 6.5mM Na2S solution；First by Hela cell with
5 μM of MB1 are incubated for 15min at 37 DEG C；Cell is washed with PBS buffer solution, then adds 100 μM SNP and 160 μM respectively
Na2S solution is incubated for 30min at 37 DEG C, finally observes on laser confocal imaging instrument, obtained 690 with 633nm excitation ±
Living cells laser confocal imaging figure in 30nm red channel, is shown in Fig. 7.
Claims (4)
1. a kind of methylene blue derivatives object, which is characterized in that be bis- (the dimethylamino) -10H- pheno thiophenes of 4- azido benzyl -3,7-
Piperazine -10- carboxylate (MB1), structural formula are as follows:
2. a kind of synthetic method of methylene blue derivatives object as described in claim 1, which is characterized in that step are as follows:
(1) in N2Under protection, condition of ice bath, 1 molar equivalent 4- aminobenzene methanol is dissolved in 10% hydrochloric acid solution；By 1-1.5
Molar equivalent sodium nitrite is dissolved in water, and is added dropwise in previous solu in 30min；Then 1-1.5 molar equivalent is folded
Sodium nitride is added portionwise wherein, and mixture is stirred to react 2h；It is extracted with ethyl acetate and water washing, collected organic layer, use is anhydrous
Sodium sulphate dries, filters, filtrate on a rotary evaporator after rotary evaporation yellow oily compound 4- triazobenzene methanol；
(2) by 1-1.2 molar equivalent 4- triazobenzene methanol, 1 molar equivalent 3, bis- (the dimethylamino) -10H- phenthazine-of 7-
10- phosgene, 2.9-3.1 molar equivalent sodium carbonate and 1 molar equivalent 4-dimethylaminopyridine are dissolved in methylene chloride, in N2It protects
15h is stirred to react under shield, condition of ice bath；It removes solvent and crude product is subjected to silica gel chromatography, obtain white solid 4-
Bis- (the dimethylamino) -10H- phenthazine -10- carboxylates (MB1) of azido benzyl -3,7-.
3. methylene blue derivatives object as described in claim 1 is in H2Application in S detection.
4. a kind of detect H with methylene blue derivatives object MB1 described in claim 12The method of S, which is characterized in that step are as follows:
(1), it prepares pH=7.4, the PBS buffer solution that concentration is 10mM, prepares the DMSO solution of the MB1 of 2mM, prepare 6.5mM
Na2The aqueous solution of S；
(2), the DMSO solution of the PBS buffer solution of 1mL pH 7.4,1mL DMSO solution and 5 μ L MB1 is added to ultraviolet colorimetric
It in ware and fluorescence cuvette, is detected on UV detector and Fluorescence spectrophotometer respectively, with when test sample is added
Between increase, the fluorescence intensity of 687nm gradually increases；
(3), the DMSO solution of the PBS buffer solution of 1mL pH 7.4,1mL DMSO solution and 5 μ L MB1 is added to other 10
In fluorescence cuvette, the Na that volume is 1,2,3,4,5,6,7,8,9,10 μ L is added respectively2S(65×10-4M) solution, glimmering
Corresponding fluorescence intensity at 687nm is measured on light spectrophotometer, with Na2The concentration of S solution is abscissa, is with fluorescence intensity
Ordinate draws figure, obtains H2The working curve of S concentration；Equation of linear regression are as follows: the unit of y=7.7529c+115.9933, c
For μM；
(4) DMSO solution of the PBS buffer solution of 1mL pH 7.4,1mL DMSO solution and 5 μ L MB1 is added to clean glimmering
In light cuvette, V μ L testing sample solution is drawn with microsyringe, is added in this fluorescence cuvette, in fluorescence spectrophotometer light
It is detected on degree instrument, the ratio measured is substituted into the equation of linear regression of step (3), obtains concentration c, sample to be tested CTo test sample=2000
μL×c×10-6/ V μ L, can acquire H2The concentration of S.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811364038.1A CN109503515A (en) | 2018-11-16 | 2018-11-16 | A kind of methylene blue derivatives object and its synthetic method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811364038.1A CN109503515A (en) | 2018-11-16 | 2018-11-16 | A kind of methylene blue derivatives object and its synthetic method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109503515A true CN109503515A (en) | 2019-03-22 |
Family
ID=65748637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811364038.1A Pending CN109503515A (en) | 2018-11-16 | 2018-11-16 | A kind of methylene blue derivatives object and its synthetic method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109503515A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111748005A (en) * | 2020-06-24 | 2020-10-09 | 河北大学 | GalNAc modified methylene blue derivative, preparation method and application thereof, liver-targeting fluorescent probe and HClO detection method |
| CN112939886A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
| CN112939887A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe based on basic dye and preparation method and application thereof |
| CN114478629A (en) * | 2021-11-24 | 2022-05-13 | 徐州医科大学 | Superoxide anion radical near-infrared fluorescent probe and preparation method and application thereof |
| CN116217515A (en) * | 2022-12-20 | 2023-06-06 | 华南师范大学 | Compound, preparation method thereof and application thereof in detection of cysteine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
| CN106749365A (en) * | 2017-01-04 | 2017-05-31 | 山西大学 | A kind of H2S detection reagents and its synthetic method and application |
| CN107290312A (en) * | 2017-06-09 | 2017-10-24 | 山西大学 | A kind of Ratio-type fluoroscopic examination H2S reagent and its synthetic method and application |
| CN107417714A (en) * | 2017-07-06 | 2017-12-01 | 南开大学 | A kind of highly sensitive fluorescence probe and its synthetic method and application based on BODIPY |
| CN108760697A (en) * | 2018-05-23 | 2018-11-06 | 山西大学 | A kind of two azole derivatives BDP-N of fluorine boron3And its preparation method and use |
-
2018
- 2018-11-16 CN CN201811364038.1A patent/CN109503515A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
| CN106749365A (en) * | 2017-01-04 | 2017-05-31 | 山西大学 | A kind of H2S detection reagents and its synthetic method and application |
| CN107290312A (en) * | 2017-06-09 | 2017-10-24 | 山西大学 | A kind of Ratio-type fluoroscopic examination H2S reagent and its synthetic method and application |
| CN107417714A (en) * | 2017-07-06 | 2017-12-01 | 南开大学 | A kind of highly sensitive fluorescence probe and its synthetic method and application based on BODIPY |
| CN108760697A (en) * | 2018-05-23 | 2018-11-06 | 山西大学 | A kind of two azole derivatives BDP-N of fluorine boron3And its preparation method and use |
Non-Patent Citations (4)
| Title |
|---|
| BIFENG CHEN,等: "Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
| JUNGEUN BAE,等: "Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue", 《CHEMICAL COMMUNICATIONS》 * |
| TATSUYA TACHIKAWA,等: "Novel color formers having a phenothiazine moiety", 《JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY,》 * |
| YING WEN，等: "Molecular isomerization triggered by H2S to an NIR accessible first direct visualization of Ca2+-dependent production in living HeLa cells", 《JOURNAL OF MATERIALS CHEMISTRY B MATERIALS FOR BIOLOGY AND MEDICINE》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111748005A (en) * | 2020-06-24 | 2020-10-09 | 河北大学 | GalNAc modified methylene blue derivative, preparation method and application thereof, liver-targeting fluorescent probe and HClO detection method |
| CN112939886A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
| CN112939887A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe based on basic dye and preparation method and application thereof |
| CN112939887B (en) * | 2021-02-04 | 2022-05-27 | 山西大学 | Near-infrared fluorescent probe based on basic dye and preparation method and application thereof |
| CN112939886B (en) * | 2021-02-04 | 2022-05-31 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
| CN114478629A (en) * | 2021-11-24 | 2022-05-13 | 徐州医科大学 | Superoxide anion radical near-infrared fluorescent probe and preparation method and application thereof |
| CN114478629B (en) * | 2021-11-24 | 2023-09-26 | 徐州医科大学 | Super-oxygen anion free radical near infrared fluorescent probe and preparation method and application thereof |
| CN116217515A (en) * | 2022-12-20 | 2023-06-06 | 华南师范大学 | Compound, preparation method thereof and application thereof in detection of cysteine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109503515A (en) | A kind of methylene blue derivatives object and its synthetic method and application | |
| Zhong et al. | A simple H2S fluorescent probe with long wavelength emission: application in water, wine, living cells and detection of H2S gas | |
| CN110540837B (en) | Preparation and application of hydrogen peroxide near-infrared fluorescent probe | |
| Li et al. | A ratiometric fluorescent probe for fast detection of hydrogen sulfide and recognition of biological thiols | |
| Geng et al. | An aqueous methylated chromenoquinoline-based fluorescent probe for instantaneous sensing of thiophenol with a red emission and a large Stokes shift | |
| CN108398409B (en) | Method for detecting hypochlorite by fluorescence ratio | |
| CN105017196B (en) | A kind of near-infrared ratio fluorescent probe of detection hydrazine and its application | |
| Yang et al. | BODIPY-based fluorescent probe for cysteine detection and its applications in food analysis, test strips and biological imaging | |
| Han et al. | Colorimetric hydrazine detection and fluorescent hydrogen peroxide imaging by using a multifunctional chemical probe | |
| CN109761978A (en) | A kind of near infrared fluorescent probe detecting benzenethiol and its synthetic method and application | |
| CN109761853A (en) | A kind of near infrared fluorescent probe detecting benzenethiol and its synthetic method and application | |
| CN107488147A (en) | A kind of fluorescence probe and preparation method and application | |
| CN109608474A (en) | A kind of compound and its preparation method and application detecting tyrosinase | |
| CN101118236A (en) | Near-infrared fluorescent detecting probe for detecting charged hydrogen in cell, synthetic method and use thereof | |
| Wang et al. | A fast-responsive two-photon fluorescent probe for detecting palladium (0) with a large turn-on fluorescence signal | |
| Liang et al. | A camphor-based fluorescent probe with high selectivity and sensitivity for formaldehyde detection in real food samples and living zebrafish | |
| Zhu et al. | An ICT-PET dual-controlled strategy for improving molecular probe sensitivity: Application to photoactivatable fluorescence imaging and H2S detection | |
| CN114539183A (en) | Lipid drop targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis, preparation and application | |
| CN110092773A (en) | A kind of oxa anthracenes derivative and its preparation method and application | |
| Sheng et al. | Cyanine IR-780 for distinguishing 2-amino thiophenols from position isomers | |
| CN110172070A (en) | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide | |
| CN106608862A (en) | Long-wavelength fluorescent probe for detecting hydrazine and synthetic method and application of long-wavelength fluorescent probe | |
| CN106008510A (en) | Hg2+ detecting aggregation-induced emission type fluorescent sensor and production method and application thereof | |
| CN110669503B (en) | Preparation and application of carbon monoxide near-infrared fluorescent probe | |
| CN109053711A (en) | A kind of probe compound and its preparation method and application for mercury ion detecting |
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 | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190322 |