CN107915680A - ATP fluorescence probes based on tetraphenyl ethylene and its preparation method and application - Google Patents
ATP fluorescence probes based on tetraphenyl ethylene and its preparation method and application Download PDFInfo
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- CN107915680A CN107915680A CN201610878175.1A CN201610878175A CN107915680A CN 107915680 A CN107915680 A CN 107915680A CN 201610878175 A CN201610878175 A CN 201610878175A CN 107915680 A CN107915680 A CN 107915680A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- 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
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- 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"
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- 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
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The present invention relates to fluorescence probe shown in a kind of logical formula (I) and preparation method thereof.The probe is with tetraphenyl ethylene (TPE) for fluorescent parent, and when probe is completely dissolved in aqueous, fluorescence signal is faint；When its aggregation or formation solid-state, fluorescence signal significantly increases.The probe has good selectivity to atriphos (ATP), can be used as ATP fluorescence probes.Fitted in aqueous solution or buffer solution, available for detecting external ATP.Such compound does not have to, by any carrier, can independently permeation cell film enter in cell, and is imaged available for intracellular ATP.The fluorescence probe of the present invention has the advantages that efficient specificity, photostability, response range are wide.
Description
Technical field
The present invention relates to a kind of tetraphenyl ethylene class ATP fluorescence probes and its preparation method and application, belong to organic molecule
Fluorescent probe technique field.
Background technology
Atriphos (ATP) is energy unit minimum in organism, directly participates in various vital movements, it is referred to as
Intracellular molecule currency.ATP is the energy source that living cells is depended on for existence, and the content of ATP is with cell metabolism and carefully in body
Born of the same parents' apoptosis has critically important relation, and the generation of many diseases such as angiocardiopathy, parkinsonism and alzheimer's disease is all
It is abnormal with ATP contents.Therefore, the detection to ATP is of great significance in life science and medicine clinical research.
At present the detection method of ATP have high performance liquid chromatography, capillary electrophoresis, bioluminescence method, electrochemistry and
Biological sensor detection etc..High performance liquid chromatography needs to expend substantial amounts of organic solvent, causes serious pollution to the environment, check fee
With height, and it is difficult to reach trace detection level；And the widely used ATP detection methods based on luciferase are although sensitive at present
Spend higher but accuracy having a great influence of being quenched of ingredient fluorescence in by matrix；And low specificity and muting sensitivity are also always electrification
Problem in Biosensors design.In short, how easier, high specific and high sensitivity detection ATP are one and grind
Study carefully hot spot.
Due to fluorescent optical sensor have the advantages that high sensitivity, selectivity it is strong, with sample amount is few, method is easy, its is fast
Short-term training is the research frontier of modern chemistry.The combination of the ATP fluorescent optical sensors and ATP studied at present depends on electrostatic
Effect, hydrogen bond action and π-π interactions, by these effects, ATP changes the structure of fluorescence molecule, the light so that it shines
Spectrum changes, and ATP is detected with this.
The content of the invention
It is an object of the invention to provide water-soluble ATP fluorescence probe of the one kind based on tetraphenyl ethylene.
Another object of the present invention is to provide the preparation method of above-mentioned water soluble compound.
A further object of the present invention is in the application in providing above-mentioned water soluble compound and being detected in ATP.
The present invention provides a kind of water miscible ATP fluorescence probes, its structure is shown in below formula (I)：
Wherein R1-R8Independent optionally H, C1-3Alkyl, C1-3Alkoxy, F, Cl, Br, I；Optionally C independent R '1-8Alkane
Base ,-(CH2CH2O)nCH3, wherein n be 1-6 integer, Z-Optionally F-、Cl-、Br-、I-。
The alkyl can be straight or branched alkyl, for example, methyl, ethyl, propyl group, butyl, isobutyl group, the tert-butyl group
Deng.
Preferably, the R1-R8Independent optionally H, CH3-、CH3O-、F。
Preferably, the group R ' it is independent optionally
It is further preferred that the logical formula (I) compound can be following particular compound：
Present invention also offers a kind of method for preparing above-mentioned logical formula (I) compound, including：By logical formula (II) compound with
Logical formula (III) compound reacts to obtain logical formula (I) compound：
Wherein, R1-R8, R ' it is as defined above.
In logical formula (II), logical formula (III), X is optionally F, Cl, Br, I, and Y is optionally F, Cl, Br, I, and X, Y can be phase at the same time
It is same or different.
According to the present invention, above-mentioned reaction carries out under solvent environment, and the solvent is preferably n,N-Dimethylformamide
(DMF) solvent.
According to the present invention, the logical formula (I) compound that above-mentioned reaction obtains can carry out separating-purifying by ion exchange method.
Such as change ammonium using Potassium Hexafluorophosphate and tetrabutyl halogen (chlorine, fluorine, bromine or iodine) and carry out ion exchange twice.
According to the present invention, the logical formula (II) compound can be prepared via a method which, including：
Wherein, R1-R8As defined above, X is optionally F, Cl, Br, I；
(a) by compound (A), palladium catalyst (II) (such as bi triphenyl phosphorus palladium chloride (II)), cuprous iodide, triphen
Base phosphorus is dissolved in solvent (preferably tetrahydrofuran), is added triethylamine and trimethyl silicane ethyl-acetylene, is obtained compound (C)；
(b) compound (B), potassium carbonate are dissolved in solvent (preferably DMF), add CH2CH2X2, wherein X be optionally F, Cl,
Br, I, obtain compound (D) after isolating and purifying；
(c) compound (C) and compound (D), zinc powder are dissolved in solvent (preferably tetrahydrofuran), add titanium tetrachloride,
Compound (E) is obtained after isolating and purifying；
(d) compound (E), tetrabutyl ammonium fluoride are dissolved in solvent (preferably dichloromethane), general formula is obtained after isolating and purifying
(II) compound.
According to the present invention, compound (A) presses 1 with trimethyl silicane ethyl-acetylene in the step (a):4 molar ratios feed intake, and double three
Phenyl phosphorus palladium chloride (II), cuprous iodide, triphenyl phosphorus, triethylamine make catalyst, and tetrahydrofuran makees solvent, and reaction temperature is
70 DEG C, reaction time 12h.
According to the present invention, compound (B) and CH in the step (b)2CH2X2By 1:6 molar ratios feed intake, and potassium carbonate is urged
Agent, DMF make solvent, and reaction temperature is 80 DEG C, reaction time 24h.
According to the present invention, compound (C) presses 1 with compound (D) in the step (c):1.2 molar ratios feed intake, zinc powder, four
Titanium chloride makees catalyst, and tetrahydrofuran makees solvent, and reaction temperature is 65 DEG C, reaction time 12h.
According to the present invention, compound (E) presses 1 with tetrabutyl ammonium fluoride in the step (d):4 molar ratios feed intake, dichloromethane
Alkane makees solvent, and reaction temperature is room temperature, reaction time 3h.
According to the present invention, the logical formula (III) compound can be prepared by the following method, including：
By two miaow methylmethanes (compound (III ')), R ' Y, reaction obtains in solvent (preferably acetonitrile), wherein, R ', Y are such as
It is defined over.
Logical formula (I) compound synthesis step of the present invention is few, and the reaction time is short, and purification is convenient, and technique is simple.
The compounds of this invention with tetraphenyl ethylene (TPE) for fluorescent parent, it is glimmering when compound is completely dissolved in aqueous
Optical signal is faint；When its aggregation or formation solid-state, fluorescence signal significantly increases.The probe has very atriphos (ATP)
Good selectivity, can be used as the fluorescence probe of ATP.
Invention further provides the purposes of above-mentioned logical formula (I) compound, it is visited as atriphos (ATP) fluorescence
Pin.
According to the present invention, detection of the logical formula (I) compound for ATP can in aqueous, can also be a variety of
Carried out in buffer solution, such as HEPES buffer solutions, Tris-HCl buffer solutions, phosphate buffer solution etc..Its luminous power with
ATP concentration increases and becomes strong.
Logical formula (I) compound of the present invention identifies ATP in aqueous solution or buffer solution, and applicable pH range is preferably
6.0-7.5, the response range to ATP are preferably 2-5000uM.
Logical formula (I) compound of the present invention, the selection to ATP have specificity, the ADP (adenosine similar with ATP structures
Diphosphonic acid), AMP (adenosine monophosphate) on the luminous power of compound of the present invention almost without influence, other same negative and positive from
The sub luminous power for compound of the present invention is almost also without influence.
Logical formula (I) compound of the present invention can independently permeation cell film enter carefully in the case where being carried without any carrier
In born of the same parents.
Logical formula (I) compound of the present invention is imaged available for intracellular ATP, after the compound enters cell,
It is observed that ATP decomposes zymolytic process by ATP by fluorescence probe under fluorescence microscope.
Brief description of the drawings
Fig. 1 be embodiment 6 prepare TPE-BIMEG in HEPES buffer solutions, with ATP concentration change and change it is glimmering
Light spectrogram.
Fig. 2 be embodiment 6 prepare TPE-BIMEG in HEPES buffer solutions, take respectively concentration be 5000uM ATP,
The fluorescence spectrum mapping of ADP, AMP probe solution.
Embodiment
The present invention is described in detail by following embodiments.But skilled in the art realises that following embodiments are not
Limiting the scope of the invention.Any improvement and change made on the basis of the present invention, all the protection model in the present invention
Within enclosing.
Embodiment 1
Prepare 4,4 '-two (trimethyl acetenyl)-benzophenone (compound 3)
Under argon gas protection, by bi triphenyl phosphorus palladium chloride (619mg, 0.88mmol), cupric iodide (223mg,
1.17mmol), triphenyl phosphorus (154mg, 0.59mmol), 4,4 '-dibromobenzo-phenone (10.0g, 29.4mmol), is dissolved in tetrahydrochysene
Furans and triethylamine in the mixed solvent, add trimethyl acetenyl silicon (16.6mL, 117.6mmol) and react 12h at 70 DEG C.So
Afterwards, reaction is quenched with 200ml saturated aqueous ammonium chlorides.Extracted with dichloromethane, organic phase is spin-dried for.Crude product solvent stone
Oily ether/dichloromethane crosses silica gel chromatographic column, obtains white solid (10.8g, 98%) MALDI-TOF (C23H26OSi2):[M]=
374.1。1H-NMR(400MHz,CDCl3,TMS):δ:7.71 (d, J=8.4Hz, 4H), 7.56 (d, J=8.4Hz, 4H),
0.27ppm(s,18H,Si(CH3)3)。
Embodiment 2
Prepare 4,4 '-two (bromine oxethyl)-benzophenone (compound 4)
Under argon gas protection, by 1,2- Bromofumes (35.1g, 186.7mmol), 4,4'-Dihydroxybenzophenone (10.0g,
46.7mmol), K2CO3(38.7g, 280.1mmol) is dissolved in DMF.48h is reacted at 90 DEG C.Reacting liquid filtering, organic phase rotation
Dry, crude product crosses silica gel chromatographic column with solvent dichloromethane/petroleum ether, obtains white solid (8g, 40%).MALDI-TOF
(C17H16Br2O3):[M-1]=427.1.1HNMR(400MHz,DMSO):δ:7.70 (d, J=8.4Hz, 4H), 7.10 (d, J=
8.4Hz, 4H), 4.43 (t, J=5.2Hz, 4H), 3.84ppm (t, J=5.2Hz, 4H).
Embodiment 3
Prepare 1,2- bis- (4,4 '-bromine oxethyl)-diphenyl -1,2- two (4,4 '-trimethyl silicane ethyl-acetylene base)-diphenyl
Ethene.(compound 5)
Under argon gas protection, by compound 3 (2.37g, 6.3mmol), compound 4 (4.51g, 10.5mmol), zinc powder
(10.95g, 168.5mmol), titanium tetrachloride (9.5mL, 84.3mol) are dissolved in tetrahydrofuran, and 12h is reacted at 65 DEG C, are used
10% saturation K2CO3Reaction is quenched in aqueous solution, and reacting liquid filtering, extracts organic phase, organic phase is spin-dried for dichloromethane.Crude product
Silica gel chromatographic column is crossed with solvent petroleum ether/dichloromethane, obtains yellow solid (1.47g, 30%).MALDI-TOF
(C40H42Br2O2Si2):[M-1]=770.1HNMR(400MHz,C3D6O),δ:7.21 (d, 4H, J=4Hz), 7.00-6.94 (m,
8H), 6.74 (d, 4H, J=8.8Hz), 4.30 (t, 4H, J=5.6Hz), 3.74 (t, 4H, J=5.6Hz), 0.20 (s, 18H).
Embodiment 4
Prepare 1,2- bis- (4,4 '-bromine oxethyl)-diphenyl -1,2- two (4,4 '-acetenyl)-diphenylethlene (chemical combination
Thing 6)
Under argon gas protection, compound 5 (2.36g, 3.1mmol), tetrabutyl ammonium fluoride (12mL, 12.4mmol) are dissolved in two
In chloromethanes, 3h is stirred at room temperature, then, adds water quenching and goes out reaction, organic phase is extracted with dichloromethane, and organic phase is spin-dried for, and is slightly produced
Thing crosses silica gel chromatographic column with solvent petroleum ether/dichloromethane, obtains yellow solid (0.78g, 40%).MALDI-TOF
(C34H26Br2O2):[M]=626.1.1HNMR(400MHz,C3D6O),δ:7.26 (d, 4H, J=8Hz), 7.04-6.95 (m,
8H), 6.75 (d, 4H, J=8Hz), 4.3 (t, 4H, J=5.6Hz), 3.74 (t, 4H, J=5.6Hz), 3.62 (s, 2H).
Embodiment 5
Prepare IMI-EG (compound 8)
Under argon gas protection, 7.4g diimidazoles methylmethane (50mmol) is dissolved in 50mL acetonitriles, is heated to 80 DEG C, adds 0.2
Ethylene glycol -2- the Bromoethyl methyl ethers of equivalent, react 48h, and cooling, solution is spin-dried for, and add acetone solution, add ethyl acetate and separate out
Clear yellow viscous thing, outwells supernatant, and ethyl acetate agitator treating 4h, outwells supernatant, obtains clear yellow viscous thing IMI-EG
(3.66g, 98%).ESI-MS(C14H23N4O3Br):[M-Br]+=295.1.1H-NMR(400MHz,DMSO),δ:9.42(s,
1H),8.04(s,1H),8.00(s,1H),7.80(s,1H),7.50(s,1H),6.99(s,1H),6.51(s,2H),4.40(t,
2H, J=12.8Hz), 3.79 (t, 2H, J=12.8Hz), 3.55-3.53 (m, 2H), 3.49-3.45 (m, 4H), 3.41-3.38
(m,2H),3.23(s,3H)。
Embodiment 6
Prepare TPE-BIMEG (compound 9)
Under argon gas protection, compound 6 (0.7g, 1.1mmol) is dissolved in DMF, adds the IMI-EG (compounds of 4 equivalents
8) 48h, is reacted at 80 DEG C, is spin-dried for, is dissolved in water, is added it in excessive hexafluorophosphoric acid aqueous solutions of potassium, by sediment
Be dissolved in acetone, be then added in excessive tetrabutylammonium chloride acetone soln, filter yellow powder TPE-BIMEG (0.4g,
30%).ESI-MS(C62H72Cl4N8O8):[M-4Cl]4+/ 4=264.4.1H-NMR (400MHz, DMSO), δ:8.27-8.15(m,
4H), 7.85 (d, 4H, J=28Hz), 7.24 (d, 4H, J=8Hz), 6.94-6.76 (m, 16H), 4.63-4.60 (m, 4H),
(4.41 t, 4H, J=4Hz), 4.29 (s, 4H), 4.18 (s, 2H), 3.79 (t, 4H, J=4Hz), 3.49-3.33 (m, 16H),
3.22(s,6H)。
Embodiment 7
TPE-BIMEG in embodiment 6 is detected for ATP：TPE-BIMEG is dissolved in 10mmolHEPES buffer solutions
In, the concentration for obtaining TPE-BIMEG is 10-5M.The ATP aqueous solutions of various concentrations are added into the solution, make that ATP's is final dense
Degree scope is 0-5000uM.Finally measure under different ATP concentration (0,5uM, 10uM, 50uM, 100uM, 1000uM, 5000uM)
The fluorescence spectrum (see attached drawing 1) of TPE-BIMEG, in Fig. 1 it can be seen from ATP concentration increase, solution fluorescence enhancing.Will
The probe solution containing 5000uM ATP, ADP, AMP measured makees fluorescence spectra (see attached drawing 2) respectively, by that can be seen in Fig. 2
Go out, fluorescence intensity of the solution at 512nm is influenced very little by ADP, AMP.
Embodiment 8
TPE-BIMEG in embodiment 6 is imaged for intracellular ATP：Two groups of HeLa cells are taken, one group is used as experimental group
ATP catabolic enzymes are added, one group is not added with ATP catabolic enzymes as a control group, cultivates 30min.TPE- is added into two tissue culture nutrient solutions
BIMEG aqueous solutions, the ultimate density for making TPE-BIMEG are 10-6M, continues to cultivate 30min.It is imaged, compares under fluorescence microscope
Group intracellular Fluorescence is very strong, and experimental group intracellular Fluorescence is very weak, this is because caused by intracellular ATP is consumed by ATP catabolic enzymes.
Claims (10)
1. the compound shown in logical formula (I)：
Wherein R1-R8Independent optionally H, C1-3Alkyl, C1-3Alkoxy, F, Cl, Br, I；Optionally C independent R '1-8Alkyl ,-
(CH2CH2O)nCH3, wherein n be 1-6 integer, Z-Optionally F-、Cl-、Br-、I-。
2. compound as claimed in claim 1, wherein, the R1-R8Independent optionally H, CH3-、CH3O-、F；The group
R ' it is independent optionally
3. compound as claimed in claim 1, wherein, the logical formula (I) compound is following particular compound：
4. the preparation method of the compound described in claim 1-3, including：By logical formula (II) compound and logical formula (III) chemical combination
Thing reacts to obtain logical formula (I) compound：
Wherein, R1-R8、R’、Z-As any one of claim 1-3 is defined；
In logical formula (II), logical formula (III), X is optionally F, Cl, Br, I, and Y is optionally F, Cl, Br, I, X, Y can at the same time to be identical or
It is different.
5. preparation method as claimed in claim 4, wherein, the reaction carries out under solvent environment, and the solvent is preferably
N,N-dimethylformamide (DMF) solvent.
6. preparation method as claimed in claim 4, wherein, the obtained logical formula (I) compound of reacting can pass through ion
Displacement method carries out separating-purifying, such as changes ammonium using Potassium Hexafluorophosphate and tetrabutyl halogen (chlorine, fluorine, bromine or iodine) and carry out two secondary ions
Exchange.
7. the purposes of claim 1-3 any one of them compounds, it is used as atriphos (ATP) fluorescence probe.
8. purposes as claimed in claim 7, wherein detection of the general formula (I) compound for ATP is in aqueous or slow
Rush in solution and carry out, the buffer solution is, for example, HEPES buffer solutions, Tris-HCl buffer solutions, phosphate buffer solution etc..
9. purposes as claimed in claim 7, wherein, the compound is imaged available for intracellular ATP.
10. a kind of fluorescence probe of detection ATP, including claim 1-3 any one of them compounds.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108849908A (en) * | 2018-07-16 | 2018-11-23 | 苏州大学 | A kind of sterilization fluorescence ionic liquid and preparation method thereof |
| CN109456349A (en) * | 2018-12-13 | 2019-03-12 | 中南民族大学 | A kind of ATP multidigit point combination fluorescence enhancement type probe molecule and its preparation method and application |
| CN110208225A (en) * | 2019-03-25 | 2019-09-06 | 东莞理工学院 | A kind of fluorescence sensor array and preparation method thereof and detecting at the same time is applied in a variety of phosphate anions |
| CN111205450A (en) * | 2018-11-22 | 2020-05-29 | 香港科技大学深圳研究院 | Application and preparation method of tetraphenylethylene isomer |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108849908A (en) * | 2018-07-16 | 2018-11-23 | 苏州大学 | A kind of sterilization fluorescence ionic liquid and preparation method thereof |
| CN111205450A (en) * | 2018-11-22 | 2020-05-29 | 香港科技大学深圳研究院 | Application and preparation method of tetraphenylethylene isomer |
| CN111205450B (en) * | 2018-11-22 | 2022-12-16 | 香港科技大学深圳研究院 | Application and preparation method of tetraphenylethylene isomer |
| CN109456349A (en) * | 2018-12-13 | 2019-03-12 | 中南民族大学 | A kind of ATP multidigit point combination fluorescence enhancement type probe molecule and its preparation method and application |
| CN109456349B (en) * | 2018-12-13 | 2021-01-29 | 中南民族大学 | ATP multi-site combined fluorescence enhanced probe molecule and preparation method and application thereof |
| CN110208225A (en) * | 2019-03-25 | 2019-09-06 | 东莞理工学院 | A kind of fluorescence sensor array and preparation method thereof and detecting at the same time is applied in a variety of phosphate anions |
| CN110208225B (en) * | 2019-03-25 | 2021-12-17 | 东莞理工学院 | Fluorescent array sensor, preparation method thereof and application of fluorescent array sensor in simultaneous detection of multiple phosphate ions |
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| CN107915680B (en) | 2019-12-03 |
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