CN105086998B - A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application - Google Patents
A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application Download PDFInfo
- Publication number
- CN105086998B CN105086998B CN201510565576.7A CN201510565576A CN105086998B CN 105086998 B CN105086998 B CN 105086998B CN 201510565576 A CN201510565576 A CN 201510565576A CN 105086998 B CN105086998 B CN 105086998B
- Authority
- CN
- China
- Prior art keywords
- probe
- hypochlorous acid
- detection
- compound
- yso
- 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.)
- Expired - Fee Related
Links
Abstract
The invention discloses a kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application, belongs to technical field of analytical chemistry.The fluorescent probe molecule formula is：C37H35N5O5S, with showing（Ⅰ）Shown structure：.The synthesis of the probe includes four steps, and last handling process is relatively easy；The selectivity quick detection of hypochlorous acid molecular probe is realized, and selectivity is good, resist other molecule interference performances strong.Additionally, with the naked eye just it is observed that the change of solution colour, along with uviol lamp it has also been observed that fluorescence color change, is a kind of fluorescent probe with the sensing function that adds lustre to.This probe can apply to detect the hypochlorous detection in living things system in intracellular lysosome, used as hypochlorous acid detection probe in intracellular lyase body.The present invention is a kind of simple, and quickly, sensitive hypochlorous acid molecular specificity detectable has broad application prospects in biomolecule detection field.
Description
Technical field
The present invention relates in a kind of quick detection cell in lysosome target hypochlorous fluorescent probe and preparation method thereof and
Using belonging to technical field of analytical chemistry.
Background technology
Active oxygen（ROS）Be in organism many physiology and pathological process play extremely important effect some it is oxygen-containing from
By base（Hydroxyl radical free radical and ultra-oxygen anion free radical etc.）And non-free radical（Hypochlorous acid and hypochlorous acid etc.）General name.Organism
It is interior to pass through enzymatic and the various ROS of non-enzymatic reaction generation under the physiology such as oxidative stress, inflammation and pathologic condition.The biology in modern age
Medical research shows that the ROS of internal generation has close relationship with the generation of some diseases, development and the aging of body.It is secondary
Chloric acid, chemical formula are HClO, are a kind of unstable weak acid, form hypochlorous acid by being passed through chlorine in pure water.In water
In solution hypochlorous acid can partial ionization generate hypochlorite and oxonium ion, in daily life, hypochlorous acid (being usually its sodium salt) is wide
It is general as bleach, deodorizer and disinfectant.In biological cell (such as neutrophil), hypochlorous acid by hypochlorous acid and chlorine from
Son is produced under the catalytic action of myeloperoxidase (MPO) (MPO).Used as a kind of important active oxygen species, hypochlorous acid is remaining thin
The redox equilibrium state of intracellular plays very important effect, but once in cell hypochlorous concentration occur it is abnormal,
Will cause including the various diseases including rheumatic arthritis, cardiovascular disease and cancer, hypochlorous acid in detection living things system
Concentration become an important problem.
But targeting is lacked to hypochlorous detection at present, it is impossible to the secondary chlorine in intracellular a certain specific organelle
Acid detected, especially lacks the hypochlorous acid probe to intracellular lysosome targeting, during lacking research cytopathy
Detection instrument to hypochlorous acid concentration's situation of change in lysosome.
The content of the invention
The present situation of problem encountered is detected for current hypochlorous acid fluorescence probe, the present invention passes through MOLECULE DESIGN,
Synthesize a kind of hypochlorous acid fluorescent probe fast and lysosome-targeting with response time.
Present invention also offers the preparation method of above-mentioned lysosome-targeting hypochlorous acid fluorescent probe and its in water environment
With the application in biological cell system.
The present invention is employed the following technical solutions：
A kind of lysosome targeting hypochlorous acid fluorescence probe, it is characterised in that the probe molecule formula is：C37H35N5O5S,
Structural formula is as follows：
。
The preparation method of above-mentioned fluorescent probe, it is characterised in that it comprises the following steps：
1）4- benzothiazole -1,3- resorcinol of the 4- lignocaines keto acid of 1.0mg with 776mg is dissolved in into 5ml methyl
In sulfonic acid, nitrogen protection, 90 DEG C are heated to reflux, and react 24 h；Reacted with the detection of TCL plates, after reaction completely, reactant liquor is cooled down
To room temperature, reactant liquor is poured slowly in 50ml frozen water, with ethanol/methylene=1:10 extractions, anhydrous sodium sulfate drying subtract
Pressure is spin-dried for solvent and obtains crude product silicagel column carrying out eluting separation, and compound L yso-1 is obtained, and Lyso-1 structural formulas are as follows：
；
2）300mg compound L yso-1 are dissolved in 10ml dehydrated alcohol, add 2ml hydrazine hydrates, nitrogen to protect, 100 DEG C
It is heated to reflux, reacts 30 min, is reacted with the detection of TCL plates, after reaction completely, reactant liquor is cooled to into room temperature, is spin-dried for, and use silicon
Glue post carries out eluting separation, can obtain compound L yso-2, and structural formula is as follows：
；
3）150mg compound L yso-2 are dissolved in 5ml chloroforms, 15 L triethylamines and 64mg chloracetyls are added at 0 DEG C
Chlorine, is gradually increased to room temperature, and 24 h are stirred at room temperature, and is reacted with the detection of TCL plates, after reaction completely, adds 1mL water quenchings to go out instead
Should, reacted with 50 mL diluted ethyl acetates, with the saturated common salt water washing of 20 mL*1 after being washed with 20 mL*2 of water, anhydrous sulfur
Sour sodium is dried, and decompression is spin-dried for solvent and obtains crude product, and carries out eluting separation with silicagel column, can obtain compound L yso-3, ties
Structure formula is as follows：
；
4）100mg compound L yso-3 are dissolved in after 5ml DMF, 34mg potassium carbonate and 41mg potassium iodide is added, under room temperature
Stirring 30min, is then added dropwise over 43mg morpholines, is stirred at room temperature overnight, and is reacted with the detection of TCL plates, after reaction completely, plus
Enter 1mL water quenchings to go out reaction, reacted with 50 mL dchloromethanes, with the saturated common salt of 20 mL*1 after being washed with 20 mL*2 of water
Water washing, anhydrous sodium sulfate drying, decompression are spin-dried for solvent and obtain crude product, and carry out eluting separation with silicagel column, can obtain mesh
Mark probe compound, is abbreviated as Lyso-ClO.
The synthetic route of above-mentioned hypochlorous acid fluorescent probe is as follows：
The step 1）Middle silicagel column elution agent proportioning is methanol：Dichloromethane=1:30.
The step 2）Middle silicagel column elution agent proportioning is ethyl acetate：Petroleum ether=1:1.
The step 3）Middle silicagel column elution agent proportioning is methanol：Dichloromethane=1:30.
The step 4）Middle silicagel column elution agent proportioning is methanol：Dichloromethane=1:30.
Present invention also offers the application of above-mentioned fluorescent probe, it is characterised in that the probe is used in water environment and biological
Hypochlorous content sensing detection in cell system；Described sensing detection include fluoroscopic examination, visual qualitative detection, cell into
As detection.
The fluorescent probe is used to detect the hypochlorous detection in living things system in intracellular lysosome, with commercialization lyase
Body is green to carry out common location experiment, and its common location coefficient is 0.98, thus this probe can be used as hypochlorous acid in intracellular lyase body
Detection probe.
It is an advantage of the invention that：（1）The synthesis of probe is easier, and last handling process is relatively easy；（2）It is of the invention real
Show the selectivity quick detection of hypochlorous acid molecular probe, and selectivity is good, resist other molecule interference performances strong.Additionally, using
Naked eyes just it is observed that the change of solution colour, along with uviol lamp it has also been observed that fluorescence color change, is one
Plant the fluorescent probe with the sensing function that adds lustre to.(3) this probe is can apply to detect in living things system in intracellular lysosome
Hypochlorous detection, by being compared with commercialization lysosome dyestuff, find this fluorescent probe to hypochlorous acid in lyase body
The coincidence factor of imaging is high, and the common location coefficient of two kinds of dyestuffs is 0.98, illustrates that this probe can be used as in intracellular lyase body times
Chloric acid detection probe.Specificity and significant color change based on this probe, its reagent also can be secondary in aqueous solution as showing
The specificity indicator that chloric acid molecule is present, can carry out real-time qualitative and quantitative optical colorimetry detection.So, the present invention is
A kind of simple, quickly, sensitive hypochlorous acid molecular specificity detectable has wide application in biomolecule detection field
Prospect.
Description of the drawings
Fig. 1 is 1 middle probe Lyso-ClO of embodiment1H NMR spectras；
Fig. 2 is probe Lyso-ClO with the hypochlorous situation of change for adding fluorogram；
Fig. 3 is selectivity fluorograms of the probe Lyso-ClO to different ions and molecule；
Fig. 4 is selectivity histogram datas of the probe Lyso-ClO to different ions and molecule, wherein 1, blank; 2、Co2 +; 3、Cu2+; 4、Ni2+; 5. Br-; 6. I-,; 7. NO2 -; 8. NO3 2-; 9. OH-; 10、S2-; 11、Cys; 12、
GHS; 13、Hcy;14th, tert-Butanol peroxide;15th, the tertiary butyl ether of peroxide; 16、 H2O2; 17、 NO; 18、HClO；
Fig. 5 is the variation diagram of probe Lyso-ClO solution solution colour before and after hypochlorous acid addition；
Fig. 6 is the change of probe Lyso-ClO solution fluorescence color after solution ultra violet lamp before and after hypochlorous acid addition
Figure；
Fig. 7 is that probe Lyso-ClO hypochlorous acid fluorescent probe detects exogenous hypochlorous acid fluorescence imaging figure, wherein a）Only
Probe ion Lyso-ClO（5μM）Fluorescence imaging light field figure；B) there was only probe ion Lyso-ClO（5μM）Blue channel is imaged
Figure；C) there was only the red passage images of probe ion Lyso-ClO, d) light field and fluorescence imaging figure overlay chart；e）Concentration and probe concentration is
5 μM be added in SiHa cells cultivate 30min after add light field figure after 20 μM of 3 min of hypochlorous acid, f）It is blue after hypochlorous acid to adding
Channel fluorescence image；g）To adding red channel fluorescence image after hypochlorous acid；H) light field e and fluorescence imaging h, g figure overlay charts
Piece；
Fig. 8 is that probe Lyso-ClO hypochlorous acid fluorescent probe detects exogenous hypochlorous acid fluorescence imaging figure and commercialization dyestuff
The red common location image of lysosome, wherein a) concentration and probe concentration is cultivated for 5 μM of red being added in A549 cells green with lyase
Light field figure after 30min, b) the red fluorescence imaging of probe molecule after commercial dyes lysosome green fluorescence image c) additions hypochlorous acid
Scheme, d) green passage and red passage stacking chart, e) green passage is compared with red passage superposition arrow head part fluorescence intensity, it is f) green logical
Road and red passage Overlapping intensities scatterplot.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail.
Embodiment 1
The preparation of target-probe compound L yso-ClO
（1）The synthesis of compound L yso-1
4- lignocaine keto acids（1.0 g, 3.19 mmol, 1 eq）With 4- benzothiazole -1,3- resorcinol（776
Mg, 3.19 mmol, 2 eq）It is dissolved in 5 mL pyrovinic acid solution, nitrogen protection, 24 h are reacted in 90 DEG C of heating.Use TCL plates
Reactant liquor, after reaction completely, is cooled to room temperature, reactant liquor is poured slowly in 50 mL frozen water, with methanol/bis- by detection reaction
Chloromethanes=1:10 extractions, anhydrous sodium sulfate drying, decompression are spin-dried for solvent and obtain crude product, and are separated with silicagel column, silica gel
Grain size is 200-300 mesh, and eluant proportioning is ethanol/methylene=1:30, yield is 64%.Synthetic route is as follows：
（2）The synthesis of compound L yso-2
Compound L yso-1（300 mg, 0.574 mmol, 1eq）It is dissolved in 10mL dehydrated alcohol, adds 2mL hydrazine hydrates,
Nitrogen is protected, and 100 DEG C are heated to reflux, and reacts 30 min, is reacted with the detection of TCL plates, after reaction completely, reactant liquor is cooled to room
Temperature, is spin-dried for, and is separated with silicagel column, and silica gel particle size is 200-300 mesh, and eluant proportioning is ethyl acetate/oil
Ether=1:1, yield is 85%.Synthetic route is as follows：
（3）The synthesis of compound L yso-3
Compound L yso-2（150 mg, 0.41 mmol, 1 eq）Be dissolved in 5 mL chloroform, three are added at 0 DEG C
15 L of ethamine and chloracetyl chloride（64 mg, 0.62 mmol, 1.5 eq）, room temperature is gradually increased to, 24 h, TLC is stirred at room temperature
Detection reaction is complete, adds 1mL water quenchings to go out reaction, with the reaction of 50 mL diluted ethyl acetates, with 20 after being washed with 20 mL*2 of water
The saturated common salt water washing of mL*1, anhydrous sodium sulfate drying, decompression are spin-dried for solvent and obtain crude product, and are separated with silicagel column,
Silica gel particle size is 200-300 mesh, and eluant proportioning is ethanol/methylene=1:30, compound L yso-3 is obtained, yield is
72%.Synthetic route is as follows：
（4）The synthesis of compound L yso-ClO
Compound L yso-3（100 mg, 0.164 mmol, 1 eq）It is dissolved in 5 mL DMF, adds K at room temperature2CO3
（34 mg, 0.245mmol, 1.5eq）And KI（41 mg, 0.245mmol, 1.5eq）Add after 30min is stirred at room temperature
Morpholine（43 mg, 0.49 mmol, 3eq）It is stirred at room temperature overnight.TLC detection reactions are complete, add 1mL water quenchings to go out instead
Should, reacted with 50 mL dchloromethanes, with the saturated common salt water washing of 20 mL*1 after being washed with 20 mL*2 of water, anhydrous sulfur
Sour sodium is dried, and decompression is spin-dried for solvent and obtains crude product, and is separated with silicagel column, and silica gel particle size is 200-300 mesh, eluting
Agent proportioning is ethanol/methylene=1:30, obtain compound L yso-ClO, yield 67%.Synthetic route is as follows：
Embodiment 2
Compound L yso-ClO hypochlorous acid fluorescent probe adds the change of the increase fluorogram of equivalent with hypochlorous acid
Lyso-ClO hypochlorous acid fluorescent probes prepared by Example 1 are dissolved in dimethyl sulfoxide（DMSO）In, make 1mmol/L
Storing solution.30 μ L are taken out from storing solution to be added in the middle of the centrifuge tube of 5mL, different equivalents are added（0-30 eq）Secondary chlorine
Sour standard solution, uses PBS buffer solution（0.1mol/L, pH=7.5）It is 1 with DMSO volume ratios:1 solution is diluted to 3 mL, with
365nm is exciting light, measures its photoluminescent property.Fluorescence spectrum is as shown in Fig. 2.From Figure 2 it can be seen that as hypochlorous acid adds equivalent
Fluorescence of the increase at 450 nm gradually weaken and the fluorescence at 585nm gradually strengthens.
Embodiment 3
Compound L yso-ClO hypochlorous acid fluorescent probe is to different molecular or the selectivity of ion
30 μ L are taken out from fluorescent probe storing solution in embodiment 2 to be added in the middle of the centrifuge tube of 5mL, is separately added into
The competition molecular criteria solution of equimolar amountss, one of hypochlorous acid standard solution for adding equimolar amountss, after 30min with
PBS:DMF (1:1) it is solvent, 365nm is exciting light, detects the fluorescence emission spectrum change of solution, as a result as shown in Figure 3.
It is investigated impact of other metal ions to fluorescence probe intensity of the present invention simultaneously, with PBS:DMF (1:1) it is solvent,
410 nm are exciting light, as a result as shown in Figure 4.Comprehensively seen by Fig. 3 and Fig. 4 it is found that other metal ions are to compound
Fluorescence of the Lyso-ClO at 585nm has little to no effect, and the addition of hypochlorite solution makes compound L yso-ClO in 585nm
The fluorescence at place is significantly increased.
Embodiment 4
Compound L yso-ClO fluorescent probes are to hypochlorous Visual retrieval
30 μ L are taken out from fluorescent probe storing solution in embodiment 2 to be added in the middle of the sample cell of 5mL, adds 80 to rub
The hypochlorous acid standard solution of your amount, hypochlorous acid can make the PBS of compound Lyso-ClO fluorescent probes：DMSO volume ratios are 1:1
There is obvious color change in buffer solution solution, solution colour becomes red from colourless, as shown in Figure 5.Along with uviol lamp
The fluorescent probe of the hypochlorous acid induction of lower macroscopic is transformed into bright red fluorescence by light blue light（Fig. 6）, explanation is one
Plant the fluorescent probe with the sensing function that adds lustre to.
Embodiment 5
Compound L yso-ClO hypochlorous acid fluorescent probe is to the exogenous hypochlorous acid fluorescence imaging of cell
The hypochlorous acid of probe application of the present invention exogenous in SiHa cells is carried out fluorescence imaging by us.Concrete operations
Step is as follows：5 μM of Lyso-ClO hypochlorous acid probe DMSO solutions are added in the culture fluid for give birth to HeLa cells in titanium dioxide
It is imaged with Laser Scanning Confocal Microscope after 30 min are cultivated in carbon incubator.Imaging results are as shown in Figure 7.Carry out first light field into
Picture, it can be seen that cell profile substantially.Then carried out exciting fluorescence imaging feelings of the observation before hypochlorous acid is not added with blue light
Condition, does not now observe fluorescent emission.After 20 μM of hypochloric acid water solution is added in system, entered with blue light after waiting 5min
Row is excited and is observed that have green glow to send, and illustrates that this fluorescent probe can carry out fluorescence imaging with the hypochlorous acid of exogenous.
Embodiment 6
Compound L yso-ClO hypochlorous acid fluorescent probe is contaminated with business lysosome to the exogenous hypochlorous acid fluorescence imaging of cell
Material common location compares
Probe application of the present invention is carried out common location experiment with business-like lysosome dyestuff in A549 cells by us, is said
Bright probe can be navigated in lysosome, and carries out fluorescence imaging application to the ectogenic hypochlorous acid in lyase body（Fig. 8）.
Concrete operation step is as follows：By 5 μM of Lyso-ClO hypochlorous acid probe DMSO solutions and commercialization lysosome dyestuff-lysosome red 5
After 30 min are cultivated in CO2 gas incubator in μM being added to the culture fluid for giving birth to A549 cells, 20 μM are added in system
Hypochloric acid water solution after, then be imaged with Laser Scanning Confocal Microscope after waiting 10 min, now used（Ex=405 nm）Swashed
Send out it is observed that having blue light to send, this is the light launched after Lyso-ClO hypochlorous acid probe is responded with hypochlorous acid, is used up（Ex =
561 nm）Carry out exciting it is observed that having HONGGUANG to send, this is the red HONGGUANG for sending of commercialization dyestuff lysosome, is entered with software
Row process can show that the common location coefficient of two kinds of dyestuffs is 0.98.
Claims (7)
1. a kind of lysosome targeting hypochlorous acid fluorescence probe, it is characterised in that the probe molecule formula is：C37H35N5O5S, knot
Structure formula is as follows：
2. the preparation method of the fluorescent probe described in a kind of claim 1, it is characterised in that it comprises the following steps：
1) the 4- benzothiazole -1,3- resorcinol by the 4- lignocaines keto acid of 1.0mg with 776mg is dissolved in 5ml pyrovinic acids
In, nitrogen protection, 90 DEG C are heated to reflux, and react 24h；Reacted with the detection of TCL plates, after reaction completely, reactant liquor is cooled to into room
Temperature, reactant liquor is poured slowly in 50ml frozen water, with ethanol/methylene=1:10 extractions, anhydrous sodium sulfate drying, decompression rotation
Dry solvent obtains crude product silicagel column and carries out eluting separation, and compound L yso-1 is obtained, and Lyso-1 structural formulas are as follows：
2) 300mg compound L yso-1 are dissolved in 10ml dehydrated alcohol, add 2ml hydrazine hydrates, nitrogen protection, 100 DEG C of heating
Backflow, reacts 30min, is reacted with the detection of TCL plates, after reaction completely, reactant liquor is cooled to room temperature, is spin-dried for, and use silicagel column
Eluting separation is carried out, compound L yso-2 can be obtained, structural formula is as follows：
3) 150mg compound L yso-2 are dissolved in 5ml chloroforms, 15 μ L triethylamines and 64mg chloracetyl chlorides are added at 0 DEG C, gradually
It is warmed to room temperature, 24h is stirred at room temperature, reacted with the detection of TCL plates, after reaction completely, adds 1mL water quenchings to go out reaction, use 50mL
Diluted ethyl acetate reacts, and the saturated common salt water washing of 20mL*1, anhydrous sodium sulfate drying, decompression are used after being washed with water 20mL*2
Being spin-dried for solvent and obtaining crude product, and eluting separation is carried out with silicagel column, can obtain compound L yso-3, structural formula is as follows：
4) 100mg compound L yso-3 are dissolved in after 5ml DMF, add 34mg potassium carbonate and 41mg potassium iodide, stirred under room temperature
30min, is then added dropwise over 43mg morpholines, is stirred at room temperature overnight, and is reacted with the detection of TCL plates, after reaction completely, adds
1mL water quenchings are gone out reaction, are reacted with 50mL dchloromethanes, with the saturated common salt washing of 20mL*1 after wash with water 20mL*2
Wash, anhydrous sodium sulfate drying, decompression is spin-dried for solvent and obtains crude product, and eluting separation is carried out with silicagel column, can obtain target spy
Pin compound.
3. the preparation method of fluorescent probe according to claim 2, it is characterised in that the step 1) in silicagel column elution
Agent proportioning is methanol：Dichloromethane=1:30.
4. the preparation method of fluorescent probe according to claim 2, it is characterised in that the step 2) in silicagel column elution
Agent proportioning is ethyl acetate：Petroleum ether=1:1.
5. the preparation method of fluorescent probe according to claim 2, it is characterised in that the step 3) in silicagel column elution
Agent proportioning is methanol：Dichloromethane=1:30.
6. the preparation method of fluorescent probe according to claim 1, it is characterised in that the step 4) in silicagel column elution
Agent proportioning is methanol：Dichloromethane=1:30.
7. the application of the fluorescent probe described in a kind of claim 1, it is characterised in that the probe is used in water environment and biology is thin
Hypochlorous sensing detection in cell space system；Described sensing detection includes fluoroscopic examination, visual qualitative detection, cell imaging inspection
Survey.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510565576.7A CN105086998B (en) | 2015-09-08 | 2015-09-08 | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510565576.7A CN105086998B (en) | 2015-09-08 | 2015-09-08 | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105086998A CN105086998A (en) | 2015-11-25 |
| CN105086998B true CN105086998B (en) | 2017-03-29 |
Family
ID=54568348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510565576.7A Expired - Fee Related CN105086998B (en) | 2015-09-08 | 2015-09-08 | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105086998B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586473A (en) * | 2018-05-30 | 2018-09-28 | 济南大学 | A kind of high selection hypersensitive peroxynitrite ratio fluorescent probe |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777768B (en) * | 2016-04-26 | 2018-03-27 | 济南大学 | It is a kind of to detect hydrogen sulfide and hypochlorous fluorescence probe and its preparation method and application in cytase body at the same time or separately |
| CN106810561A (en) * | 2017-01-04 | 2017-06-09 | 济南大学 | A kind of lysosome targeting hypochlorous acid ratio fluorescent probe and preparation method and application |
| CN106967078B (en) * | 2017-03-17 | 2019-03-15 | 济南大学 | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation and application |
| CN108218898A (en) * | 2017-06-13 | 2018-06-29 | 泰山医学院 | The preparation and application of a kind of hypochlorous acid ratio fluorescent probe of novel targeted lysosome |
| CN109781678B (en) * | 2017-11-14 | 2022-03-18 | 山东第一医科大学(山东省医学科学院) | Preparation and application of ratiometric fluorescent probe applied to intramitochondrial hypochlorous acid detection |
| CN108516980A (en) * | 2018-05-24 | 2018-09-11 | 泰山医学院 | A kind of preparation and application of the rhodamine hypochlorous acid fluorescence probe that can target lysosome |
| CN108530459B (en) * | 2018-05-30 | 2020-09-15 | 杭州佰迈贝生物科技有限公司 | Preparation method of fluorescent probe |
| CN108732150A (en) * | 2018-05-30 | 2018-11-02 | 杭州佰迈贝生物科技有限公司 | The method for detecting peroxynitrite in sample |
| CN108717055A (en) * | 2018-05-30 | 2018-10-30 | 杭州佰迈贝生物科技有限公司 | The purposes of high selection hypersensitive peroxynitrite ratio fluorescent probe |
| CN109232615A (en) * | 2018-11-02 | 2019-01-18 | 泰山医学院 | Across the key energy transfer hypochlorous acid fluorescence probe of one kind and its lysosome hypochlorous acid detection in apply |
| CN109851622B (en) * | 2019-01-22 | 2021-08-31 | 济南大学 | Hypochlorite fluorescent probe targeting lysosome |
| CN112920157B (en) * | 2021-02-03 | 2023-03-07 | 山西大学 | Benzene coupling benzopyran derivative and synthesis method and application thereof |
| CN113354618B (en) * | 2021-06-02 | 2022-12-20 | 济南大学 | Hypochlorous acid fluorescent probe capable of targeting cell lysosome, preparation method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101302220A (en) * | 2007-05-08 | 2008-11-12 | 中国科学院化学研究所 | N-benzoyl rhodamine B hydrazine, preparation and use thereof |
| CN102994072A (en) * | 2012-12-12 | 2013-03-27 | 东华大学 | Fluorescent probe for detecting hypochlorite aions, and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101096654B1 (en) * | 2009-04-16 | 2011-12-21 | 이화여자대학교 산학협력단 | Novel rhodamine derivatives and sensor for detecting hypochlorous acid comprising the same |
-
2015
- 2015-09-08 CN CN201510565576.7A patent/CN105086998B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101302220A (en) * | 2007-05-08 | 2008-11-12 | 中国科学院化学研究所 | N-benzoyl rhodamine B hydrazine, preparation and use thereof |
| CN102994072A (en) * | 2012-12-12 | 2013-03-27 | 东华大学 | Fluorescent probe for detecting hypochlorite aions, and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| A rhodamine hydrazide-based fluorescent probe for sensitive and selective detection of hypochlorous acid and its application in living cells;Zhen Zhang等;《Anal. Methods》;20141016;第7卷;107–114 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586473A (en) * | 2018-05-30 | 2018-09-28 | 济南大学 | A kind of high selection hypersensitive peroxynitrite ratio fluorescent probe |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105086998A (en) | 2015-11-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105086998B (en) | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation method and application | |
| CN106281310B (en) | A kind of Mitochondrially targeted hydrogen peroxide molecule fluorescence probe and its preparation method and application | |
| CN105777768B (en) | It is a kind of to detect hydrogen sulfide and hypochlorous fluorescence probe and its preparation method and application in cytase body at the same time or separately | |
| CN105419788B (en) | A kind of small-molecule fluorescent probe for identifying hydrogen sulfide and its preparation method and application | |
| 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 | |
| CN107056774B (en) | A kind of hypochlorous acid fluorescence probe and its preparation method and application | |
| CN106967078A (en) | A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation and application | |
| CN106967102B (en) | A kind of enhanced fluorescence probe of hydrogen peroxide based on Rhodamine Derivatives | |
| CN105694857B (en) | A kind of Mitochondrially targeted nitrosyl hydrogen molecule fluorescence probe and its preparation method and application | |
| CN108117544A (en) | A kind of reversible sulfur dioxide/sulfurous acid（Hydrogen）The fluorescence probe of salt | |
| CN104949946B (en) | A kind of application of fluorescence probe in hydrogen peroxide molecule detection | |
| CN109053791A (en) | A kind of hypochlorous acid near infrared fluorescent probe and its preparation method and application based on silicon rhodamine | |
| CN106810561A (en) | A kind of lysosome targeting hypochlorous acid ratio fluorescent probe and preparation method and application | |
| Ding et al. | Design, synthesis and bioimaging application of a novel two-photon xanthene fluorescence probe for ratiometric visualization of endogenous peroxynitrite in living cells and zebrafish | |
| CN109266331A (en) | A kind of near infrared fluorescent probe, preparation method and application for surveying hypochlorite ion based on half flower cyanines structure | |
| CN111072648A (en) | Fluorescent probe for detecting biological thiol in lysosome as well as preparation method and application thereof | |
| CN107987049A (en) | A kind of Fluorescence Increasing type two-photon hypochlorous acid fluorescence probe and its preparation method and application | |
| CN109608474A (en) | A kind of compound and its preparation method and application detecting tyrosinase | |
| CN109503515A (en) | A kind of methylene blue derivatives object and its synthetic method and application | |
| CN114539183A (en) | Lipid drop targeting and biological thiol sensitive fluorescent probe for cancer cell tissue diagnosis, preparation and application | |
| CN106543251A (en) | Nitric oxide production water-soluble fluorescent probe and its application in a kind of detection hepatocyte | |
| Zheng et al. | Development of fast-response turn-on phosphorescent probes for biothiols based on ruthenium (II) complexes | |
| CN106103430A (en) | For detecting the fluorescent probes based on double triflate of superoxide anion radical | |
| US8187825B2 (en) | Thiol detection method | |
| Wu et al. | A highly selective and sensitive fluorescence probe based on Rhodol for imaging of endogenous peroxynitrite in living cells |
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: 20170329 Termination date: 20200908 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |