CN110372738A - A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide - Google Patents
A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide Download PDFInfo
- Publication number
- CN110372738A CN110372738A CN201910692990.2A CN201910692990A CN110372738A CN 110372738 A CN110372738 A CN 110372738A CN 201910692990 A CN201910692990 A CN 201910692990A CN 110372738 A CN110372738 A CN 110372738A
- Authority
- CN
- China
- Prior art keywords
- preparation
- fluorescence
- hydrogen sulfide
- fluorescence probe
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/089—Treatments not covered by a preceding group
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- 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
Abstract
The present invention provides a kind of fluorescence probes for detecting hydrogen sulfide:.Above-mentioned fluorescence probe can be used for detecting solution, hydrogen sulfide and fat drips in cell or organism.Fluorescence probe fast response time of the invention, stability is high, and when detecting hydrogen sulfide, 15 min reach stable state；Strong interference immunity.
Description
Technical field
The invention belongs to technical field of analytical chemistry, and in particular to it is a kind of detection hydrogen sulfide and fat drips fluorescence probe and its
Preparation method and application.
Background technique
Hydrogen sulfide is a kind of inorganic compound, is a kind of colourless, inflammable sour gas, band when concentration is low under normal circumstances
Stench, smell such as addled egg；Instead without smell (because the hydrogen sulfide of high concentration can benumb olfactory nerves) when concentration is high.Its energy
It is dissolved in water, is a kind of weak acid, when it is heated, hydrogen sulfide escapes in water again.Hydrogen sulfide (H2It S is) after carbon monoxide and an oxygen
After changing nitrogen, the third can play the endogenous gas signaling molecule of physiological action in life entity.Hydrogen sulfide is a kind of acute
Severe toxicity, sucking a small amount of high-concentration hydrogen sulfide can be in fatal in the short time.Low concentration contact only has the local stimulation of respiratory tract and eye
Effect, general action is more apparent when high concentration, shows as central nervous system symptom and asphyxia symptom.The gas molecule is in painstaking effort
Important physiological and pathological adjustment effect is responsible in pipe and nervous system.Therefore, design and synthesize the good, high sensitivity of specificity,
And the fluorescence probe with good biocompatibility, real-time and accurately the intracorporal concentration of hydrogen sulfide of biology can be detected
It all anticipates with important guidance with imaging for the prevention of disease, diagnosis, detection, treatment and physiopathologic further investigation
Justice.
Currently, mainly passing through the detection means such as spectrophotometry, electrochemical assay, gas chromatography, liquid chromatography
To detect hydrogen sulfide.These methods apply in general to the hydrogen sulfide in detection aqueous solution and food, are not suitable for bioenvironmental
The detection of hydrogen sulfide, because their detection sensitivity is limited and has destructiveness to biological sample.Quickly detection, Yi Guancha
The hydrogen sulfide fluorescence probe of signal intensity is necessary.
Fat drips are an important subcellular organelles, and indispensable role is played in cell, for example, cell membrane is formed,
Lipoprotein is formed and intracellular signal transduction.Fat drips are mainly made of neutral lipid, including triacylglycerol and cholesteryl ester, table
Face is covered by single layer phosphatide, and memebrane protein is embedded in above.Fat drips are not only present in fat cell, and are prevalent in from thin
Bacterium cell is into the most cells of mammalian cell.The storage and consumption of fatty acid are strictly adjusted, if fat drips exist
Unbalance in this adjusting will lead to that metabolic disorder is such as fat and diabetes.Therefore, the real-time dynamic monitoring of fat drips is also mesh
Preceding important research direction.In recent years, extensive concern of the small molecule organic fluorescent probe by scientific circles, it and specific objective divide
After analysis object is had an effect, fluorescence signal can change, to achieve the purpose that detection.Have using the fluorescence analysis of fluorescence probe
There are the features such as specific selectivity, high sensitivity, response time be fast, and non-invasive imaging inspection is carried out to intracellular target molecule
Survey can be monitored in real time, and image is concretely observed signal intensity.So invention can detect H simultaneously2The fluorescence probe of S and fat drips
It is very important.
Summary of the invention
For the problems of the prior art, the present invention provides a kind of fluorescence probe for detecting hydrogen sulfide and fat drips, response speed
Spend fast, strong antijamming capability.
It is a further object of the present invention to provide a kind of above-mentioned fluorescence probe detection solution in or biological cell in hydrogen sulfide
Application.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of fluorescence probe detecting hydrogen sulfide, abbreviation H-LDS, shown in chemical structural formula such as formula (I):
The preparation method of above-mentioned fluorescence probe, comprising the following steps:
(1) in N2Under protection, bromo- 1, the 8- naphthalene acid anhydride of 4- and NaN3In K2CO3Reaction is heated under catalysis in DMF, separating-purifying obtains
Compound 2；
(2) compound 2 and aminopropyl disiloxane obtained by step (1) are protected from light heating reaction, isolate and purify to obtain fluorescence in ethyl alcohol
Probe H-LDS.
In step (1), bromo- 1, the 8- naphthalene acid anhydride of the material 4- and NaN3The mass ratio of the material are as follows: 1:1.5.
In step (1), the reaction time is 2h.
In step (1), the heating temperature is 45 DEG C.
In step (1), the separating-purifying step is to pour into reaction solution in ice water, drying is filtered, with absolute dichloromethane
Column chromatographic purifying is carried out for eluant, eluent, removes methylene chloride with Rotary Evaporators.
In step (2), the compound 2 is 2:1 with aminopropyl disiloxane the mass ratio of the material.
In step (2), the reaction time is 4h.
In step (2), the heating temperature is 65 DEG C.
In step (2), the separating-purifying step is the ethyl alcohol removed in reaction solution, is with volume ratio with silica gel column chromatography
The methylene chloride and methanol of 30:1 is eluant, eluent, and purifying obtains compound 3.
A kind of application of above-mentioned fluorescence probe hydrogen sulfide and fat drips in detection solution, cell or organism.
Mechanism of the invention is as follows:
Fluorescence probe H-LDS main chain of the invention has Si-O-Si and naphthalimide structure simultaneously, and fluorescence probe and hydrogen sulfide are anti-
It answers, azido group is reduced into amino, the fluorescence enhancement at 550nm.Since there are siloxane structures in probe, it is easy in rouge
It is enriched in drop, when there is no H2S there are when probe do not had in fat drips fluorescence exist, work as H2S there are when probe exist
Green fluorescence is shown in fat drips.
The invention has the following advantages that
Fluorescence probe of the invention can be used for detecting solution, cell and the intracorporal hydrogen sulfide of biology.Fast response time, stability
Height, when detecting hydrogen sulfide, 15min reaches stable state；Strong interference immunity.Meanwhile the fluorescence probe can also be used to position cell
Fat drips.
Detailed description of the invention
Fig. 1 is fluorescence probe H-LDS1H NMR spectra；
Fig. 2 is fluorescence probe H-LDS13C NMR spectra；
The fluorescence spectra of the ion selectivity of Fig. 3 fluorescence probe H-LDS；
Fig. 4 fluorescence probe H-LDS is in various concentration H2Fluorescence spectra under the conditions of S；
Fig. 5 fluorescence probe H-LDS is to H2The time response fluorogram of S；
Fig. 6 fluorescence probe H-LDS is in cell to the response diagram of H2S；
Fig. 7 fluorescence probe H-LDS is in cell to the positioning figure of fat drips.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
The synthesis of 1 fluorescence probe H-LDS of embodiment
(1) bromo- 1, the 8- naphthalene acid anhydride of 4- (1.2g, 4mmol) is dissolved in 15ml DMF, NaN is then added3(0.4 g,
6mmol), the K of catalytic amount is added2CO3, in N2It is protected from light 45 DEG C under protection and is heated to return stirring reaction 2 hours；It then will reaction
Liquid pours into ice water, filters drying, is further purified with silica gel column chromatography by eluant, eluent of absolute dichloromethane, uses Rotary Evaporators
Methylene chloride is removed, compound 2 is obtained.
(2) it weighs compound 2 (0.524g, 2mmol) obtained by step (1) to be dissolved in ethyl alcohol, two silicon of aminopropyl is then added
Oxygen alkane (0.249g, 1mmol), is protected from light 68 DEG C and is heated to reflux and be stirred to react 4h, then removes the ethyl alcohol in reaction solution, uses layer of silica gel
Analysis column is further purified to obtain compound 3 as eluant, eluent using volume ratio for the methylene chloride and methanol of 30:1, and gained compound 3 is
Fluorescence probe H-LDS.Its1H NMR spectra such as Fig. 1,13C NMR spectra such as Fig. 2.
1H NMR(400MHz,CDCl3) δ 8.67-8.60 (m, 3H), 8.47-8.40 (dd, J=20.1,8.4Hz, 2H),
8.12 (d, J=8.5Hz, 1H), 7.79-7.67 (m, 1H), 7.46 (dd, J=23.0,8.0Hz, 2H), 6.90 (d, J=
8.5Hz, 1H), 4.22-4.09 (m, 4H), 2.67 (t, J=7.0Hz, 2H), 0.71-0.61 (m, 4H), 0.55-0.47 (m,
2H),0.06(s, 12H).
13C NMR(100MHz,CDCl3)δ(ppm):163.9,163.5,143.4,132.1,131.7,129.2,128.7,
126.8, 124.3,45.4,27.7,15.36,0.32
The fluorescence spectrum of 2 fluorescence probe H-LDS ion selectivity of embodiment
The ethanol solution mother liquor for preparing 1 gained fluorescence probe of 1mmol embodiment is spare.10ul probe mother liquor is taken to be dissolved in 3ml PBS
With the mixed solution (25 μM of PBS buff, pH=7.4,10% ethyl alcohol) of ethyl alcohol, then take 20 equivalents various ionic liquids (1,
Probe；2,Cys,3,D-Cys；4,EtOONH4；5,Glu；6,Gly；7,kNO3；8,NaNO2； 9,Na2S2O3；10,NaBr；11,
NaCl；12,NaClO；13,NaCNS；14,NaF；15,NaHCO3； 16,NaI；17,Na2SO3；18,Na2SO4；19,Na2CO3；
20、Na2S2O4；21, NaHS) enter into mixed liquor, sufficiently after reaction, its fluorescence property (λ is tested with sepectrophotofluorometerex=
405nm, slit width: excitation 5mm emits 2.5mm).Fluorescence spectrum is as shown in Figure 3.From the figure 3, it may be seen that when probe addition is other
In 550nm fluorescence intensity, there is no too big variations when ion, but as addition H2Fluorescence intensity is at 550nm when S
There is apparent enhancing to illustrate probe to H2S has high identification.
4 fluorescence probe H-LDS of embodiment is to various concentration H2The response of S
The ethanol solution mother liquor for preparing 1 gained fluorescence probe of 1mmol embodiment is spare.10ul probe mother liquor is taken to be dissolved in 3ml PBS
With the mixed solution (25 μM of PBS buff, pH=7.4,10% ethyl alcohol) of ethyl alcohol.10mmol H is configured with deionized water2S is same
The H of concentration gradient2What (0,1,2,3,4,5,6,7,8,9,10,12,14,16,18,20,22,24,25 μm) of S addition was uniformly mixed
In ionic liquid, fluorescence probe H-LDS fluorescence property (λ is tested with sepectrophotofluorometerex=405nm, slit width: excitation
5mm emits 2.5mm).As shown in Figure 4, with the H that various concentration gradient is added into probe2S has found glimmering at 550nm
Luminous intensity constantly enhances, and illustrates probe to H2S has good response.
5 fluorescence probe H-LDS of embodiment is to H2The response dynamics of S are tested.
The ethanol solution mother liquor for preparing 1 gained fluorescence probe of 1mmol embodiment is spare.30 μ L probe mother liquors are taken to be dissolved in 3 ml
The mixed solution (25 μM of PBS buff, pH=7.4,10% ethyl alcohol) of PBS and ethyl alcohol.10 mmol are configured with deionized water
NaHS takes 25 μm of H2S and probe reaction, setting spectral temporal interval 1min sweep primary (λexSlit width :=405 nm swash
5mm is sent out, 2.5mm is emitted), fluorescence probe H-LDS is to H2Response dynamics curve such as Fig. 5 of S.As shown in Figure 5, it is sufficiently reacting
Fluorescence intensity no longer changes after 15min, and intensity keeps almost unchanged in 20min, illustrates that fluorescence probe has good light
Stability.
6 fluorescence probe H-LDS of embodiment is in cell to H2The response of S
HeLa cell is in 35mm culture dish with 3 × 105The density culture of cell/ware, HeLa cell is in 37 DEG C, 5%CO2Training
It supports and is cultivated for 24 hours in case, then remove waste liquid, washed 2 times with phosphate buffer solution (PBS, pH=7.4), 1ml cell is added
Culture solution cultivates 15min with 1 μM of ultimate density of probe H-LDS, (λ is then imaged under two-photon fluorescence microscopeex=
405nm).Then in situ on the basis of H is added dropwise2S (25 μM), continues to be imaged, and imaging results are shown in Fig. 6, (a), (b), (c) for not
Add the cell state before NaHS, we it will be clear that do not observe apparent green light in green fluorescence channel,
It (d), (e), (f) is the cell state that NaHS is added, it is apparent green glimmering to observing after 20 μM of NaHS are added in situ
Light, round point shape is presented in shape, this shows that fluorescence probe can be in cell to H2S response.
7 fluorescence probe H-LDS of embodiment is in cell to the positioning of fat drips
Cultured cell addition H-LDS (1 μM) is incubated for 15min jointly, 0.5 μM of commercial dyes Nile red then is added again
It is incubated for 5min, (λ is then imagedex=405nm, λex=561nm), as a result such as Fig. 7, (a) they are the Composite Field of (b) (c) (e),
We are it will be clear that apparent yellow punctate fluorescence in figure, this is because (b) green fluorescence channel (probe and H2S is anti-
Ying Houyong 405nm excitation) and (c) (probe and Nile red business fat drips dyestuff are sharp with 561nm after being incubated for jointly for red fluorescence channel
Hair) can be good coincidence the reason of.As shown in Figure 7, green channel only has faint green light when beginning, and H is added2Green is glimmering after S
Light is gradually increased until maximum, and green round point shape fluorescence is overlapped with the fluorescence height of red Nile red, is redyed index and is said 0.87
We bright probe can position well in fat drips.
Claims (8)
1. a kind of fluorescence probe for detecting hydrogen sulfide, chemical structural formula are as follows:
。
2. a kind of preparation method of fluorescence probe as described in claim 1, which comprises the following steps:
(1) in N2Under protection, bromo- 1, the 8- naphthalene acid anhydride of 4- and NaN3In K2CO3Reaction is heated under catalysis in DMF, separating-purifying obtains
Compound 2:；
(2) compound 2 and aminopropyl disiloxane obtained by step (1) are protected from light heating reaction, isolate and purify to obtain fluorescence in ethyl alcohol
Probe.
3. preparation method according to claim 2, which is characterized in that in step (1), bromo- 1, the 8- naphthoic acid of material 4-
Acid anhydride and NaN3The mass ratio of the material is 1:1.5；The compound 2 is 2:1 with aminopropyl disiloxane the mass ratio of the material.
4. preparation method according to claim 2, which is characterized in that in step (1), the heating temperature is 45 DEG C；
Reaction time is 2 h.
5. preparation method according to claim 2, which is characterized in that in step (1), the separating-purifying step is will be anti-
It answers liquid to pour into ice water, filters drying, carry out column chromatographic purifying by eluant, eluent of absolute dichloromethane, remove two with Rotary Evaporators
Chloromethanes.
6. preparation method according to claim 2, which is characterized in that in step (2), the heating temperature is 65 DEG C；Instead
It is 4 h between seasonable.
7. preparation method according to claim 2, which is characterized in that in step (2), the separating-purifying step is to remove
Ethyl alcohol in reaction solution, with silica gel column chromatography using volume ratio for 30:1 methylene chloride and methanol as eluant, eluent, purifyingization
Close object 3.
8. a kind of fluorescence probe as described in claim 1 is in detection solution, cell or organism in hydrogen sulfide and fat drips
Using.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910692990.2A CN110372738A (en) | 2019-07-30 | 2019-07-30 | A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910692990.2A CN110372738A (en) | 2019-07-30 | 2019-07-30 | A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110372738A true CN110372738A (en) | 2019-10-25 |
Family
ID=68256956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910692990.2A Pending CN110372738A (en) | 2019-07-30 | 2019-07-30 | A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110372738A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110927137A (en) * | 2019-12-31 | 2020-03-27 | 吉林大学 | Single-benzene-ring framework-based cell lipid drop fluorescence imaging probe and application thereof |
| CN112945913A (en) * | 2019-12-10 | 2021-06-11 | 中国科学院大连化学物理研究所 | Application of naphthalimide fluorescent probe in field of lipid drop imaging |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804725A (en) * | 2014-01-28 | 2015-07-29 | 中国科学院大连化学物理研究所 | Fluorescent probe for detecting H2S in lysosome and its synthesis method and use |
| CN106083888A (en) * | 2016-07-12 | 2016-11-09 | 济南大学 | A kind of detect the fluorescent probe of hydrogen sulfide in cancerous cell |
| CN106279278A (en) * | 2016-08-09 | 2017-01-04 | 济南大学 | A kind of have Mitochondrially targeted hydrogen sulfide fluorescence probe with two-phpton property and its preparation method and application |
| CN107298654A (en) * | 2017-05-19 | 2017-10-27 | 济南大学 | The fluorescence probe of hydrogen sulfide in a kind of detection endoplasmic reticulum |
| CN107531908A (en) * | 2015-04-02 | 2018-01-02 | 波利默里克斯有限公司 | Fluorescence silicone elastomer, the method and purposes for synthesizing it |
| CN109320453A (en) * | 2018-11-08 | 2019-02-12 | 山西大学 | The 1,8- naphthalimide derivative and its synthetic method of a kind of symmetrical structure and application |
| CN109932349A (en) * | 2019-04-04 | 2019-06-25 | 济南大学 | A kind of hypochlorous organosilicon small-molecule fluorescent probe of detection |
| CN110031436A (en) * | 2019-04-12 | 2019-07-19 | 济南大学 | A kind of organosilicon fluorescence probe detecting fat drips |
-
2019
- 2019-07-30 CN CN201910692990.2A patent/CN110372738A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804725A (en) * | 2014-01-28 | 2015-07-29 | 中国科学院大连化学物理研究所 | Fluorescent probe for detecting H2S in lysosome and its synthesis method and use |
| CN107531908A (en) * | 2015-04-02 | 2018-01-02 | 波利默里克斯有限公司 | Fluorescence silicone elastomer, the method and purposes for synthesizing it |
| CN106083888A (en) * | 2016-07-12 | 2016-11-09 | 济南大学 | A kind of detect the fluorescent probe of hydrogen sulfide in cancerous cell |
| CN106279278A (en) * | 2016-08-09 | 2017-01-04 | 济南大学 | A kind of have Mitochondrially targeted hydrogen sulfide fluorescence probe with two-phpton property and its preparation method and application |
| CN107298654A (en) * | 2017-05-19 | 2017-10-27 | 济南大学 | The fluorescence probe of hydrogen sulfide in a kind of detection endoplasmic reticulum |
| CN109320453A (en) * | 2018-11-08 | 2019-02-12 | 山西大学 | The 1,8- naphthalimide derivative and its synthetic method of a kind of symmetrical structure and application |
| CN109932349A (en) * | 2019-04-04 | 2019-06-25 | 济南大学 | A kind of hypochlorous organosilicon small-molecule fluorescent probe of detection |
| CN110031436A (en) * | 2019-04-12 | 2019-07-19 | 济南大学 | A kind of organosilicon fluorescence probe detecting fat drips |
Non-Patent Citations (2)
| Title |
|---|
| XIAONI WANG 等: "Triphenylamine Schiff base as a lipid droplet-targeted fluorescent probe using Si-O-Si as a bridge for the detection of Cr6+ applied in bio-imaging", 《ANALYST》 * |
| 高敏 等: "检测硫化氢分子的荧光探针", 《化学进展》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112945913A (en) * | 2019-12-10 | 2021-06-11 | 中国科学院大连化学物理研究所 | Application of naphthalimide fluorescent probe in field of lipid drop imaging |
| CN110927137A (en) * | 2019-12-31 | 2020-03-27 | 吉林大学 | Single-benzene-ring framework-based cell lipid drop fluorescence imaging probe and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106279278B (en) | It is a kind of that there is Mitochondrially targeted and two-phpton property hydrogen sulfide molecule fluorescence probe and its preparation method and application | |
| Zhou et al. | An NBD fluorophore-based colorimetric and fluorescent chemosensor for hydrogen sulfide and its application for bioimaging | |
| CN103805170B (en) | A kind of for identifying specificity fluorescent probe and the application thereof of hydrogen sulfide | |
| CN105524612B (en) | A kind of isophorone class fluorescence probe and its preparation and application | |
| Wang et al. | A highly sensitive and selective near-infrared fluorescent probe for imaging hydrazine in living tissues and mice | |
| Lan et al. | A simple pyrene–hemicyanine fluorescent probe for colorimetric and ratiometric detection of SO2 derivatives in the mitochondria of living cells and zebrafish in vivo | |
| CN106967102B (en) | A kind of enhanced fluorescence probe of hydrogen peroxide based on Rhodamine Derivatives | |
| Yuan et al. | Reaction-based fluorescent probe for hydrogen sulfide with large signal-to-noise ratio in living cells and tissues | |
| JP6281727B2 (en) | Specific fluorescent probe and quantitative method based on pseudoesterase hydrolysis reaction of albumin | |
| CN105542752B (en) | A kind of formaldehyde fluorescence probe and its preparation method and application | |
| CN108844931B (en) | Simultaneous detection of SO with LZQ fluorescent probe2Derivatives and use in HSA | |
| Yin et al. | A dual-emission and mitochondria-targeted fluorescent probe for rapid detection of SO2 derivatives and its imaging in living cells | |
| CN105693703A (en) | Novel rate type fluorescent probe for intracellular lysosome pH imaging | |
| CN108997326A (en) | A kind of mercaptan fluorescence probe and its preparation method and application | |
| CN106939015B (en) | A kind of malonaldehyde fluorescence probe and its preparation method and application | |
| CN105038762A (en) | Ratio-dependent fluorescent probe for detecting hydrogen peroxide and application of ratio-dependent fluorescent probe | |
| CN111253935A (en) | Two-photon fluorescent probe for detecting polarity and viscosity through two channels and preparation method and application thereof | |
| CN109336815A (en) | Hypochlorous two-photon fluorescence probe in a kind of detection endocytoplasmic reticulum | |
| CN110372738A (en) | A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide | |
| Long et al. | An ultralow concentration of two-photon fluorescent probe for rapid and selective detection of lysosomal cysteine in living cells | |
| CN111072648A (en) | Fluorescent probe for detecting biological thiol in lysosome as well as preparation method and application thereof | |
| CN114539183B (en) | Lipid-droplet targeting and biological thiol-sensitive fluorescent probe for cancer cell tissue diagnosis and preparation and application thereof | |
| CN105985769B (en) | A kind of preparation and application of benzenethiol fluorescence probe | |
| Zhou et al. | A highly sensitive fluorescent probe for selective detection of cysteine/homocysteine from glutathione and its application in living cells and tissues | |
| CN112500386A (en) | Near-infrared HClO fluorescent probe based on pyrrazone oxime, and preparation 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 | ||
| AD01 | Patent right deemed abandoned |
Effective date of abandoning: 20221018 |
|
| AD01 | Patent right deemed abandoned |