CN104946248A - Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof - Google Patents
Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof Download PDFInfo
- Publication number
- CN104946248A CN104946248A CN201510400148.9A CN201510400148A CN104946248A CN 104946248 A CN104946248 A CN 104946248A CN 201510400148 A CN201510400148 A CN 201510400148A CN 104946248 A CN104946248 A CN 104946248A
- Authority
- CN
- China
- Prior art keywords
- bisulfite
- acid hydrogen
- probe
- sulphurous acid
- fluorescent 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.)
- Granted
Links
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
The invention discloses a water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe. The probe is 3-((3'-benzimidazole)-carbonyl propylene)-7-diethylin coumarin containing alpha, beta-unsaturated ketone, and the chemical structural formula is displayed as a first formula. The probe and a sulphurous acid hydrogen root can be selectively acted, red color is changed into blue color, and naked eye distinguishment can be achieved, a fluorescent ratio response effect is obtained, and analysis can be conducted through ultraviolet absorption and the fluorospectrophotometry. Sulphurous acid hydrogen root ions can be detected in a ratio mode, ratio imaging inside cells is achieved, and the content of the sulphurous acid hydrogen root in a liquid sample can rapidly detected by made test strips. The probe is expected to play a role in industrial manufacture and food detection and biological science, a wide application prospect is obtained.
Description
Technical field
The present invention relates to a kind of bisulfite fluorescent probe, particularly relate to a kind of water-soluble bisulfite ratio fluorescent probe and application thereof; Belong to organic molecule fluorescent probe field.
Background technology
Coumarin fluorescent group itself has larger molar extinction coefficient and quantum yield, can reach near-infrared luminous after modifying, and can be used for luminescent material, chemical sensor and mark biomolecules.Utilized ratio fluorescent effect detection bisulfite in recent years, and the research of imaging obtains development in active somatic cell.
Sulphite is worldwide widely used foodstuff additive, and can be used as food preservatives and SYNTHETIC OPTICAL WHITNER, be highly effective antiseptic-germicide.Human body is from also producing sulfurous acid ion in metabolic process, but the sulphite of high density can cause people to suffer from diarrhoea, allergy, blood pressure reduction, asthma etc., WHO specifies that the permission intake of everyone sulphite every day is 0-0.7mg/kg (in sulfurous gas).Now discharge a large amount of sulfurous gas in the industrial production, the acid rain heavy corrosion buildings of formation and crops, and the excessive acidifying in rivers and lakes can be caused.Therefore in biology and actual sample, convenient and swift detection sulphite needs keeping punching of scientific researcher.
The detection method of the sulphite existed at present has chromatography, sensor method, electrochemical process, capillary electrophoresis and zymotechnic coupling etc., but these methods have very large limitation, as complicated, time-consuming in expensive equipment, process etc., is unfavorable for detection.[CN102072901B] in the patent of having applied for, [CN103743726A] can not use large-scale instrument to detect sulphite in food, but can only be used for the detection of liquid-like.And emerging fluorescent method has easy to operate, sensitivity high.The patent [CN102924530B] of having authorized, [CN102659677B] illustrate the probe of specific detection sulphite, but there is single signal respectively detects and cannot the shortcoming of cell imaging.Based on this, exploitation there is cell imaging ability, and can ratio test, bore hole identification bisulfite fluorescent probe become problem urgently to be resolved hurrily at present.
Summary of the invention
For the deficiencies in the prior art, the problem to be solved in the present invention is to provide a kind of water-soluble bisulfite ratio fluorescent probe and application thereof.
Water-soluble bisulfite ratio fluorescent probe of the present invention, it is characterized in that: described fluorescent probe is containing α, 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin of alpha, beta-unsaturated ketone, its chemical structural formula is such as formula shown in (I)
The preparation method of above-mentioned water-soluble bisulfite ratio fluorescent probe is: synthesize 3-aldehyde radical-7-diethylaminocoumarin and 5-ethanoyl benzoglyoxaline by currently known methods; then the two is obtained by reacting 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin, and single crystal structure is as Fig. 1.
Above-mentioned water-soluble bisulfite ratio fluorescent probe is detecting containing the application in bisulfite sample.
In above-mentioned application: the described bisulfite sample that contains is preferably biomass cells, the food containing bisulfite or the solution containing bisulfite.
The application in bisulfite open hole detection test paper prepared by water-soluble bisulfite ratio fluorescent probe of the present invention.
Probe 3-of the present invention ((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin can occur to step gram addition reaction with bisulfite in aqueous, block conjugated system, as shown in Figure 2, discharge tonka bean camphor blue-fluorescence, thus reach the effect of detection.
Concrete: the solution of the PBS damping fluid (CTAB 1mM, pH=7.4) of preparation 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin, quantitatively adds the Cys of micro updating respectively, GSH, mercaptoethanol, PA, HSO
3 -, CH
3cO
2 -, ClO
3 -, CN
-, CO
3 2-, H
2pO
4 -, HCO
3 2-, HPO
4 2-, F
-, Cl
-, Br
-, I
-, IO
3-, NO
2-, NO
3 -, S
2-, S
2o
3 2-, SO
3 2-, SO
4 2-the aqueous solution.It is tried to the selectivity of different mercaptan, Common Anions and responding ability by ultraviolet-visible spectrophotometry and Tissue with Spectrofluorometric.Result display probe 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin has good selectivity to bisulfite, add the blue shift that bisulfite cross-reference display fluorescence emission wavelengths there occurs 147nm, there is extraordinary rate responsive.See Fig. 3,4.
Add 1.0 μMs 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin A549 viable cell in do not add NaHSO
3with add NaHSO
3compared with control cells fluorescent staining micro-imaging changes.Fluorescence imaging display 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin penetrates in cell.Control group A cell blue channel unstressed configuration, red channel light tone fluorescence.Control group B blue channel shows fluorescence, red channel fluorescent quenching.See Fig. 5.
At different concns NaHSO
3add 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin filter paper of 0.01mg/mL in the aqueous solution, observe change in fluorescence under visible ray and ultraviolet lamp.Result display increases with concentration of sodium bisulphite, and under visible ray, test paper is become light blue from incarnadine, and under ultraviolet lamp, test paper becomes blueness from redness.See Fig. 6.
Water-soluble bisulfite ratio fluorescent probe 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin provided by the invention can optionally with bisulfite effect, become light blue from redness, can discernable by eye, there is ratio fluorescent response effect, also can be analyzed by uv-absorbing and fluorimetry.Not only can ratio test sulfurous acid hydrogen radical ion, realize intracellular ratio imaging, and the test strip made can open hole detection liquid-like sulfite hydrogen radical content rapidly.Be expected to play a role in industrial production and food inspection and bio-science, have broad application prospects.
Accompanying drawing explanation
Fig. 1 is 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin single crystal structure schematic diagram.
Fig. 2 is the high resolution mass spectrum of 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin and sodium bisulfite adduct.
Fig. 3 is the ultraviolet absorpting spectrum that the solution of the PBS damping fluid (CTAB 1mM, pH=7.4) of 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin adds Common Anions and multiple mercaptan.
Fig. 4 is the fluorescent emission collection of illustrative plates that the solution of the PBS damping fluid (CTAB 1mM, pH=7.4) of 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin adds Common Anions and multiple mercaptan.
Fig. 5 is that 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin is at A549 intracellular Fluorescence micro-imaging figure.
Wherein: A group is under 37 DEG C of conditions, A549 cell add 1.0 μMs 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin cell culture fluid in cultivate 1 hour; B group be A549 cell add 1.0 μMs 2-(3-ethanoyl) tonka bean camphor base acrylate cell culture fluid in cultivate 1 hour, after PBS buffered soln washs three times, and then containing 5mM NaHSO
3cell culture fluid in soak the image of 0.5 hour.
Fig. 6 is the photo that 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin obtains under visible ray and ultraviolet lamp as the test paper detecting bisulfite.
Wherein: with 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin solution soaking filter paper of 0.01mg/mL, test strip is made in oven dry, then aqueous solution of sodium bisulfite (a:0, b:1 × 10 of different concns are immersed
-5m, c:1 × 10
-4m, d:1 × 10
-3m, e:1 × 10
-2m, f:1 × 10
-1m), take pictures under visible ray and ultraviolet lamp.
Embodiment
Embodiment 1
Synthesize 3-aldehyde radical-7-diethylaminocoumarin and 5-ethanoyl benzoglyoxaline by currently known methods, then the two is obtained by reacting 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin with red fluorescence.Specifically:
By 3-aldehyde radical-7-diethylaminocoumarin (1; 5.0mmol); 5-ethanoyl benzoglyoxaline (2; 7.5mmol) join in 100mL dehydrated alcohol with 1mL piperidines; be heated to backflow; react and be chilled to room temperature after 9 hours; red solid is had to separate out; suction filtration; ethanol washes three times; thick product ethyl alcohol recrystallization obtains bright red solid and is 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin (BICO), fusing point: 287-292 DEG C, productive rate 61%.Fig. 1 is shown in by monocrystalline.
Infrared analysis (KBr, cm
-1): 3250 (NH), 3063 (ArH), 2969 (CH
2cH
3), 1721 (C=O), 1563 (C=C).
Nuclear magnetic resonance hydrogen spectruming determining:
1h NMR (400MHz, DMSO-d
6): δ=1.09 (t, J=7.0Hz, 6H, CH
3), 3.47 (q, J=7.0Hz, 4H, CH
2), 6.60 (d, J=2.0Hz, 1H, ArH), 6.78 (dd, J=2.0and 9.0Hz, 1H, ArH), 7.35-7.37 (m, 2H, ArH), 7.54 (d, J=9.0Hz, 1H, ArH), 7.59 (s, 1H, ArH), 7.83 (d, J=15.8Hz, 1H ,-CO-CH=), 7.88 (s, 1H, ArH), 8.40 (d, J=15.8Hz, 1H ,=CH-Ar), 8.45 (s, 1H, 4-H of coumarin), 13.39 (s, 1H, NH).
Carbon-13 nmr spectra measures:
13c NMR (100MHz, DMSO-d
6): 12.83,44.85,96.67,108.99,110.43,113.46,121.27,131.43,140.31,147.25,149.83,152.62,175.04,160.15,181.51.
High resolution mass spectrum: m/z [M+H]
+calcd for C
23h
22n
3o
3: 388.1661, found 388.1670.
3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin can occur to step gram addition reaction with bisulfite in aqueous, blocks conjugated system, discharges tonka bean camphor blue-fluorescence.Its reaction process is shown below:
Embodiment 2
With microsyringe respectively to PBS damping fluid (the CTAB 1mM filling 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin that 10mL prepares, pH=7.4) in solution, quantitatively add the Cys of 10 equivalents respectively, GSH, mercaptoethanol, PA, HSO
3 -, CH
3cO
2 -, ClO
3 -, CN
-, CO
3 2-, H
2pO
4 -, HCO
3 2-, HPO
4 2-, F
-, Cl
-, Br
-, I
-, IO
3-, NO
2-, NO
3 -, S
2-, S
2o
3 2-, SO
3 2-, SO
4 2-the aqueous solution, act on after 1 hour and carry out ultraviolet-visible spectrophotometry and Tissue with Spectrofluorometric examination, display probe 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin has good selectivity to bisulfite, add the blue shift that bisulfite cross-reference display fluorescence emission wavelengths there occurs 147nm, there is extraordinary rate responsive.See Fig. 3,4.
Embodiment 3
Intracellular Fluorescence imaging test:
A, B two groups is control group, control group A: under 37 DEG C of conditions, A549 cell add 1.0 μMs 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin cell culture fluid in cultivate 1 hour; Control group B:A549 cell add 1.0 μMs 2-(3-ethanoyl) tonka bean camphor base acrylate cell culture fluid in cultivate 1 hour, after PBS buffered soln washs three times, and then containing 5mM NaHSO
3cell culture fluid in soak 0.5 hour.
Fluorescence imaging display 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin penetrates in cell.Control group A cell blue channel unstressed configuration, red channel light tone fluorescence.Control group B blue channel shows fluorescence, red channel fluorescent quenching.See Fig. 5.
Embodiment 4
Probe of the present invention is tested as bisulfite test paper:
With 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin solution soaking filter paper of 0.01mg/mL, dry and make test strip, then immerse aqueous solution of sodium bisulfite (a:0, b:1 × 10 of different concns
-5m, c:1 × 10
-4m, d:1 × 10
-3m, e:1 × 10
-2m, f:1 × 10
-1m), take pictures under visible ray and ultraviolet lamp.
Result: increase with concentration of sodium bisulphite, under visible ray, test paper is become light blue from incarnadine, and under ultraviolet lamp, test paper becomes blueness from redness.See Fig. 6.
Claims (4)
1. a water-soluble bisulfite ratio fluorescent probe, it is characterized in that: described fluorescent probe is containing α, 3-((3 '-benzoglyoxaline)-carbonyl propylene)-7-diethylaminocoumarin of alpha, beta-unsaturated ketone, its chemical structural formula is such as formula shown in (I)
2. water-soluble bisulfite ratio fluorescent probe according to claim 1 contains the application in bisulfite sample in open hole detection.
3. apply as claimed in claim 2, it is characterized in that: described is biomass cells, the food containing bisulfite or the solution containing bisulfite containing bisulfite sample.
4. the application in bisulfite open hole detection test paper prepared by water-soluble bisulfite ratio fluorescent probe according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510400148.9A CN104946248B (en) | 2015-07-09 | 2015-07-09 | Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510400148.9A CN104946248B (en) | 2015-07-09 | 2015-07-09 | Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104946248A true CN104946248A (en) | 2015-09-30 |
| CN104946248B CN104946248B (en) | 2017-04-26 |
Family
ID=54161321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510400148.9A Expired - Fee Related CN104946248B (en) | 2015-07-09 | 2015-07-09 | Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104946248B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749142A (en) * | 2016-11-15 | 2017-05-31 | 山西大学 | A kind of SO32‑/HSO3‑Detection reagent and its synthetic method and application |
| CN106946902A (en) * | 2017-04-11 | 2017-07-14 | 济南大学 | A kind of sulfur dioxide Near-infrared Double photon ratio fluorescent probe and preparation method thereof |
| CN107474044A (en) * | 2017-08-10 | 2017-12-15 | 河北大学 | A kind of coumarin derivatives, its preparation method and application and a kind of bisulfite detection kit |
| CN108102647A (en) * | 2018-03-06 | 2018-06-01 | 泰山医学院 | Imidazopyridine cyanofuran class inferior sulfate radical fluorescence probe and its application |
| CN108285448A (en) * | 2017-10-12 | 2018-07-17 | 泰山医学院 | Pyrido [1,2-a] the benzimidazole SO of benzimidazole modification32-Ratio fluorescent probe and its application |
| CN108484625A (en) * | 2018-05-30 | 2018-09-04 | 济南大学 | A kind of colorimetric fluorescence probe of quick high-selectivity sensitive analysis bisulfite |
| CN108623575A (en) * | 2017-03-21 | 2018-10-09 | 泰山医学院 | A kind of fluorescence probe that is simple and effectively detecting sulphite |
| CN109187455A (en) * | 2018-08-13 | 2019-01-11 | 天津理工大学 | It is a kind of detect sulphite in foods content kit and its application |
| CN110655510A (en) * | 2019-09-12 | 2020-01-07 | 山东大学 | Sulfite ratiometric fluorescent probe targeting lipid droplets and application thereof |
| CN111380845A (en) * | 2020-03-06 | 2020-07-07 | 谭锐 | Application of coumarin probe in quantitative detection of sulfur dioxide |
| CN113372282A (en) * | 2021-07-01 | 2021-09-10 | 齐齐哈尔大学 | Fluorescent probe for detecting bisulfite ions in real time and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659677A (en) * | 2012-04-28 | 2012-09-12 | 中南大学 | Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof |
| CN102924530A (en) * | 2012-11-22 | 2013-02-13 | 中山大学 | Iridium complex as well as preparation method and application thereof to detection of sulfur dioxide |
-
2015
- 2015-07-09 CN CN201510400148.9A patent/CN104946248B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659677A (en) * | 2012-04-28 | 2012-09-12 | 中南大学 | Fluorescent molecular probe for detecting sulfite ions through naked eyes and fluorescence ratio as well as synthesis and application thereof |
| CN102924530A (en) * | 2012-11-22 | 2013-02-13 | 中山大学 | Iridium complex as well as preparation method and application thereof to detection of sulfur dioxide |
Non-Patent Citations (2)
| Title |
|---|
| HAIYU TIAN ET AL.: "Colorimetric and ratiometric fluorescent detection of sulfite in water via cationic surfactant-promoted addition of sulfite to α,β-unsaturated ketone", 《ANALYTICA CHIMICA ACTA》 * |
| 齐海萍: "苯并咪唑类比率型荧光探针的合成及应用研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749142B (en) * | 2016-11-15 | 2019-01-25 | 山西大学 | A kind of SO32-/HSO3-Detection reagent and its synthetic method and application |
| CN106749142A (en) * | 2016-11-15 | 2017-05-31 | 山西大学 | A kind of SO32‑/HSO3‑Detection reagent and its synthetic method and application |
| CN108623575B (en) * | 2017-03-21 | 2020-04-10 | 山东第一医科大学(山东省医学科学院) | Simple and effective fluorescent probe for detecting sulfite |
| CN108623575A (en) * | 2017-03-21 | 2018-10-09 | 泰山医学院 | A kind of fluorescence probe that is simple and effectively detecting sulphite |
| CN106946902B (en) * | 2017-04-11 | 2019-03-01 | 济南大学 | A kind of sulfur dioxide near-infrared-two-photon ratio fluorescent probe and preparation method thereof |
| CN106946902A (en) * | 2017-04-11 | 2017-07-14 | 济南大学 | A kind of sulfur dioxide Near-infrared Double photon ratio fluorescent probe and preparation method thereof |
| CN107474044A (en) * | 2017-08-10 | 2017-12-15 | 河北大学 | A kind of coumarin derivatives, its preparation method and application and a kind of bisulfite detection kit |
| CN107474044B (en) * | 2017-08-10 | 2019-12-06 | 河北大学 | Coumarin derivative, preparation method and application thereof, and bisulfite detection kit |
| CN108285448A (en) * | 2017-10-12 | 2018-07-17 | 泰山医学院 | Pyrido [1,2-a] the benzimidazole SO of benzimidazole modification32-Ratio fluorescent probe and its application |
| CN108102647A (en) * | 2018-03-06 | 2018-06-01 | 泰山医学院 | Imidazopyridine cyanofuran class inferior sulfate radical fluorescence probe and its application |
| CN108484625A (en) * | 2018-05-30 | 2018-09-04 | 济南大学 | A kind of colorimetric fluorescence probe of quick high-selectivity sensitive analysis bisulfite |
| CN109187455A (en) * | 2018-08-13 | 2019-01-11 | 天津理工大学 | It is a kind of detect sulphite in foods content kit and its application |
| CN109187455B (en) * | 2018-08-13 | 2021-10-15 | 天津理工大学 | Kit for detecting content of sulfite in food and application thereof |
| CN110655510A (en) * | 2019-09-12 | 2020-01-07 | 山东大学 | Sulfite ratiometric fluorescent probe targeting lipid droplets and application thereof |
| CN110655510B (en) * | 2019-09-12 | 2021-12-10 | 山东大学 | Sulfite ratiometric fluorescent probe targeting lipid droplets and application thereof |
| CN111380845A (en) * | 2020-03-06 | 2020-07-07 | 谭锐 | Application of coumarin probe in quantitative detection of sulfur dioxide |
| CN113372282A (en) * | 2021-07-01 | 2021-09-10 | 齐齐哈尔大学 | Fluorescent probe for detecting bisulfite ions in real time and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104946248B (en) | 2017-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104946248A (en) | Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof | |
| 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 | |
| CN105017196B (en) | A kind of near-infrared ratio fluorescent probe of detection hydrazine and its application | |
| Peng et al. | A novel fluorescent probe for selective detection of hydrogen sulfide in living cells | |
| CN105038766A (en) | Visible and reversible ratiometric fluorescent probe as well as preparation method and application thereof | |
| CN106946902B (en) | A kind of sulfur dioxide near-infrared-two-photon ratio fluorescent probe and preparation method thereof | |
| CN108129428B (en) | Ratiometric fluorescent probe for detecting bisulfite and application thereof | |
| CN108003869B (en) | Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof | |
| CN105885831B (en) | Thiosemicarbazides contracting umbelliferone -8- aldehyde probe reagent and its preparation and application | |
| CN107021953A (en) | A kind of coumarin fluorescent probe and preparation method and its application on detection hypochlorite ion | |
| CN113121513B (en) | Carbazole-coumarin hydrazone compound as well as preparation method and application thereof | |
| CN113999219B (en) | Double-site fluorescent probe and synthetic method and application thereof | |
| CN109336815A (en) | Hypochlorous two-photon fluorescence probe in a kind of detection endocytoplasmic reticulum | |
| CN107286151B (en) | Carbazole-based two-photon fluorescent probe and preparation method and application thereof | |
| CN106518855B (en) | It is a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen and its application | |
| CN108329301B (en) | Two-photon pH ratio measurement fluorescent probe for monitoring autophagy of cells and preparation method and application thereof | |
| CN106749142B (en) | A kind of SO32-/HSO3-Detection reagent and its synthetic method and application | |
| CN111205220B (en) | Fluorescent probe and preparation method and application thereof | |
| CN107488446A (en) | A kind of colorimetric Ratio-type soda acid fluorescence probe and its preparation method and application | |
| CN114835636B (en) | Naphthalene-vinyl pyridyl dual-response fluorescent probe and preparation method and application thereof | |
| CN108373464B (en) | Formaldehyde fluorescent probe based on formaldehyde-induced catalysis of succinimide hydrolysis and preparation method and application thereof | |
| CN110669503A (en) | Preparation and application of carbon monoxide near-infrared fluorescent probe | |
| CN113307763B (en) | Amino acid derivative, preparation method thereof and application of amino acid derivative as acid-base indicator and fluorescent probe | |
| Yang et al. | Ratiometric fluorescence sensing of endogenous sulfur dioxide derivatives: Bio-imaging application in lipid droplets | |
| CN105777591B (en) | A kind of curcumin derivate and its preparation and the application in benzenethiol is detected |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20170426 Termination date: 20210709 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |