CN107915680B - ATP fluorescence probe based on tetraphenyl ethylene and its preparation method and application - Google Patents
ATP fluorescence probe based on tetraphenyl ethylene and its preparation method and application Download PDFInfo
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- CN107915680B CN107915680B CN201610878175.1A CN201610878175A CN107915680B CN 107915680 B CN107915680 B CN 107915680B CN 201610878175 A CN201610878175 A CN 201610878175A CN 107915680 B CN107915680 B CN 107915680B
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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 probes 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 solution, fluorescence signal is faint；When its aggregation or formation solid-state, fluorescence signal is significantly increased.The probe has good selectivity to atriphos (ATP), can be used as ATP fluorescence probe.It is fitted in aqueous solution or buffer solution, can be used for detecting external ATP.Such compound does not have to by any carrier, can independently permeation cell film enter in cell, and can be used for intracellular ATP imaging.Fluorescence probe of the invention has many advantages, such as 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 small organic molecule
Fluorescent probe technique field.
Background technique
Atriphos (ATP) is the smallest energy unit 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, the content Yu cell metabolism of ATP and thin in body
Born of the same parents' apoptosis has critically important relationship, and the generation of many diseases such as cardiovascular disease, parkinsonism and alzheimer's disease is all
It is abnormal along with ATP content.Therefore, it is of great significance in life science and medicine clinical research to the detection of ATP.
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 a large amount of organic solvent, causes serious pollution to the environment, check fee
With height, and it is difficult to reach trace detection level；And the ATP detection method based on luciferase being widely used at present is although sensitive
Higher but accuracy is spent to be affected by what ingredient fluorescence in matrix was quenched；And low specificity and muting sensitivity are also always electrification
Problem in Biosensors design.In short, how easier, high specific and highly sensitive detection ATP are one and grind
Study carefully hot spot.
Due to fluorescent optical sensor have many advantages, such as high sensitivity, selectivity it is strong, with sample amount is few, method is easy, it is fast
Short-term training is the research frontier of modern chemistry.The combination of the ATP fluorescent optical sensor and ATP studied at present depends on electrostatic
Effect, hydrogen bond action and π-π interaction, are acted on by these, and ATP changes the structure of fluorescent molecule, the light so that it shines
Spectrum changes, and detects ATP with this.
Summary of the invention
Water-soluble ATP fluorescence probe the purpose of the present invention is to provide one kind based on tetraphenyl ethylene.
Another object of the present invention is to provide the preparation methods of above-mentioned water soluble compound.
Another object of the present invention is to provide application of the above-mentioned water soluble compound in ATP detection.
The present invention provides a kind of water-soluble ATP fluorescence probe, structure is as follows shown in logical formula (I):
Wherein R1-R8Independent optionally H, C1-3Alkyl, C1-3Alkoxy, F, Cl, Br, I；The independent optionally C of R '1-8Alkane
Base ,-(CH2CH2O)nCH3, wherein n is the integer of 1-6, Z-Optionally F-、Cl-、Br-、I-。
The alkyl can be linear or branched alkyl group, for example, methyl, ethyl, propyl, butyl, isobutyl group, tert-butyl
Deng.
Preferably, the R1-R8Independent optionally H, CH3-、CH3O-、F。
Preferably, the group R ' is independent optionally
It is further preferred that the logical formula (I) compound can be following particular compound:
The present invention also provides a kind of methods for preparing above-mentioned logical formula (I) compound, comprising: 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 simultaneously
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 changes 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, comprising:
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), and triethylamine and trimethyl silicane ethyl-acetylene is added, obtains compound (C)；
(b) compound (B), potassium carbonate are dissolved in solvent (preferably DMF), CH is added2CH2X2, 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), titanium tetrachloride are added,
Compound (E) is obtained after isolating and purifying；
(d) compound (E), tetrabutyl ammonium fluoride are dissolved in solvent (preferably methylene chloride), general formula is obtained after isolating and purifying
(II) compound.
According to the present invention, compound (A) feeds intake with trimethyl silicane ethyl-acetylene by 1:4 molar ratio in the step (a), 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)2CH2X2It feeds intake by 1:6 molar ratio, potassium carbonate is urged
Agent, DMF make solvent, and reaction temperature is 80 DEG C, and the reaction time is for 24 hours.
According to the present invention, compound (C) feeds intake with compound (D) by 1:1.2 molar ratio in the step (c), 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) and tetrabutyl ammonium fluoride feed intake by 1:4 molar ratio in the step (d), 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, comprising:
By two miaow methylmethanes (compound (III ')), R ' Y, reaction is obtained 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, simple process.
The compounds of this invention with tetraphenyl ethylene (TPE) be fluorescent parent, it is glimmering when compound is completely dissolved in aqueous solution
Optical signal is faint；When its aggregation or formation solid-state, fluorescence signal is significantly increased.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, are used as atriphos (ATP) fluorescence and visit
Needle.
According to the present invention, the logical formula (I) compound can in aqueous solution for the detection of ATP, can also be a variety of
It is carried out in buffer solution, such as HEPES buffer solution, Tris-HCl buffer solution, 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 has specificity, the ADP (adenosine similar with ATP structure to the selection of ATP
Diphosphonic acid), AMP (adenosine monophosphate) on the luminous power of compound of the present invention almost without influence, other same yin-yang from
Son for compound of the present invention luminous power almost also without influence.
Logical formula (I) compound of the present invention can independently permeation cell film enter carefully in the case where carrying without any carrier
In born of the same parents.
Logical formula (I) compound of the present invention can be used for intracellular ATP imaging, after the compound enters cell, In
It is observed that ATP decomposes zymolytic process by ATP by fluorescence probe under fluorescence microscope.
Detailed description of the invention
Fig. 1 is the TPE-BIMEG of the preparation of embodiment 6 in HEPES buffer solution, changes with ATP concentration and changes glimmering
Light spectrogram.
Fig. 2 be embodiment 6 prepare TPE-BIMEG in HEPES buffer solution, take respectively concentration be 5000uM ATP,
The fluorescence spectrum of ADP, AMP probe solution is mapped.
Specific 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 improvements and changes made on the basis of the present invention, all in protection model of the invention
Within enclosing.
Embodiment 1
Prepare 4,4 '-two (trimethyl acetenyl)-benzophenone (compound 3)
Under protection of argon gas, by bi triphenyl phosphorus palladium chloride (619mg, 0.88mmol), cupric iodide (223mg,
1.17mmol), triphenyl phosphorus (154mg, 0.59mmol), 4,4 '-dibromobenzo-phenones (10.0g, 29.4mmol), is dissolved in tetrahydro
Furans and triethylamine in the mixed solvent are added trimethyl acetenyl silicon (16.6mL, 117.6mmol) and react 12h at 70 DEG C.So
Afterwards, with 200ml saturated aqueous ammonium chloride quenching reaction.It is extracted with dichloromethane, organic phase is spin-dried for.Crude product solvent stone
Oily ether/methylene chloride 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- Bromofume (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.Reaction solution filtering, organic phase rotation
Dry, crude product crosses silica gel chromatographic column with solvent methylene chloride/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
Ethylene.(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 K2CO3Aqueous solution quenching reaction, reaction solution filtering, is extracted with dichloromethane organic phase, organic phase is spin-dried for.Crude product
Silica gel chromatographic column is crossed with solvent petroleum ether/methylene chloride, 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
Object 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, water quenching reaction is added, organic phase is extracted with dichloromethane, and organic phase is spin-dried for, thick to produce
Object crosses silica gel chromatographic column with solvent petroleum ether/methylene chloride, 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
It prepares IMI-EG (compound 8)
Under argon gas protection, 7.4g diimidazole methylmethane (50mmol) is dissolved in 50mL acetonitrile, is heated to 80 DEG C, is added 0.2
Ethylene glycol -2- the Bromoethyl methyl ether of equivalent reacts 48h, cooling, and solution is spin-dried for, acetone solution is added, and ethyl acetate is added and is precipitated
Clear yellow viscous object outwells supernatant, and ethyl acetate agitator treating 4h outwells supernatant, obtains clear yellow viscous object 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
It prepares TPE-BIMEG (compound 9)
Under argon gas protection, compound 6 (0.7g, 1.1mmol) is dissolved in DMF, the IMI-EG (compound of 4 equivalents is added
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 used for ATP detection: TPE-BIMEG is dissolved in 10mmolHEPES buffer solution
In, the concentration for obtaining TPE-BIMEG is 10-5M.The ATP aqueous solution of various concentration is added into the solution, makes that ATP's is final dense
Degree range is 0-5000uM.It finally measures 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.It will
The probe solution containing 5000uM ATP, ADP, AMP measured makees fluorescence spectra (see attached drawing 2) respectively, by that can see in Fig. 2
Out, fluorescence intensity of the solution at 512nm is influenced very little by ADP, AMP.
Embodiment 8
TPE-BIMEG in embodiment 6 is used for intracellular ATP imaging: taking two groups of HeLa cells, one group is used as experimental group
ATP catabolic enzyme is added, one group is not added ATP catabolic enzyme as a control group, cultivates 30min.TPE- is added into two groups of culture solutions
BIMEG aqueous solution makes the ultimate density 10 of TPE-BIMEG-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 intracellular ATP is caused by the consumption of ATP catabolic enzyme.
Claims (12)
1. logical formula (I) compound represented:
Wherein R1-R8Independent optionally H, C1-3Alkyl, C1-3Alkoxy, F, Cl, Br, I；The independent optionally C of R '1-8Alkyl ,-
(CH2CH2O)nCH3, wherein n is the integer of 1-6, Z-Optionally F-、Cl-、Br-、I-。
2. compound as described in claim 1, wherein the R1-R8Independent optionally H, CH3-、CH3O-,F；The group
R ' is independent optionally
3. compound as described in claim 1, wherein the logical formula (I) compound is following particular compound:
4. the preparation method of the described in any item compounds of claim 1-3, comprising: by logical formula (II) compound and general formula
(III) compound 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, and X, Y may be the same or different.
5. preparation method as claimed in claim 4, wherein the reaction carries out under solvent environment, and the solvent is N, N-
Dimethylformamide (DMF) solvent.
6. preparation method as claimed in claim 4, wherein the obtained logical formula (I) compound that reacts can pass through ion
Displacement method carries out separating-purifying.
7. preparation method as claimed in claim 6, wherein carry out two secondary ions using Potassium Hexafluorophosphate and tetrabutyl ammonium halide
Exchange.
8. the purposes of the described in any item compounds of claim 1-3 is used as atriphos (ATP) fluorescence probe.
9. purposes as claimed in claim 8, wherein the general formula (I) compound is in aqueous solution or slow for the detection of ATP
It rushes in solution and carries out.
10. purposes as claimed in claim 9, wherein the buffer solution is HEPES buffer solution, Tris-HCl buffering is molten
Liquid, phosphate buffer solution.
11. purposes as claimed in claim 8, wherein the compound can be used for intracellular ATP imaging.
12. a kind of fluorescence probe for detecting ATP, including the described in any item compounds of claim 1-3.
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| 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 |
| 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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