CN107089937A - Mitochondrially targeted fluorescence probe for determining viscosity and its preparation method and application - Google Patents
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- LQNUZADURLCDLV-UHFFFAOYSA-N [O-][N+](c1ccccc1)=O Chemical compound [O-][N+](c1ccccc1)=O LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention has synthesized one kind using carbazole as fluorophor by MOLECULE DESIGN, has Mitochondrially targeted viscosity fluorescence probe by mitochondria positioning group of nitrogen cation.Present invention also offers the application that a kind of simple and convenient process for preparing of the fluorescence probe and the fluorescence probe carry out sensing detection to the viscosity of solution and organelle microenvironment.The reagent can carry out real-time qualitative and quantitative colorimetric determination as the indicator in the aqueous solution with viscosity B coefficent in biological cell.The fluorescence probe of the present invention is a kind of simple, and quickly, sensitive viscosity specific detection agents have broad application prospects in biomolecule detection field.
Description
Technical field
The present invention relates to it is a kind of detect mitochondria in viscosity fluorescence probe and its preparation with using spectrum test, cell into
The methods such as picture detection solution and cell viscosity, belong to organic molecule fluorescence probe field.
Background technology
Viscosity is to weigh the mobility and diffusible principal element of a kind of dense fluid, while being fluid diffusion rate
Primary Reference index.The viscosity of microenvironment plays very important effect in pathological research, because intracellular different zones
With different viscosity, the change of viscosity often influences various metabolic progress in cell micro-environment.When cell is in
During pathological state, intracellular viscosity will change.When anomalous variation occurs for intracellular viscosity number, membrane-bound protein can be influenceed
White activity, suppression insulin synthesis etc., cause to produce relevant disease.The fortune of material and signal in viscosity pole earth effect cytoplasm
It is defeated, the interaction between large biological molecule, and ROS and the RNS diffusion on a cellular level that active metabolism is produced.
Intracellular viscosity plays very important effect in biosystem, and the change of different zones viscosity can cause
The change or the generation of disease of corresponding physiological function.Mitochondria is the warehouse that cell produces energy, and the change of viscosity can be reduced
The mobility of mitochondrial membrane, so as to increase ROS generation.Proved extensively, increase mitochondrial viscosity and may result in one
A little diseases, such as Alzheimer's disease, Parkinson's, diabetes etc..Therefore, quantization cell mitochondrial viscosity is particularly significant.Tradition
The method of detection viscosity has：Capillary viscometer, falling ball viscometer, rotation viscometer etc..But conventional viscometer is easily caused
Sample pollutes, and causes larger measurement error, also, can only detect plasma viscosity, it is impossible to realize to being glued in cell or tissue sample
The detection of degree.Relatively conventional detection method, fluorescent spectrometry has the features such as simple to operate, response is rapid, spatial resolution is high,
The real-time monitoring in cell, tissue is had been carried out, is played an important role in biological field.But at present can be to line grain
The fluorescence probe that internal viscosity carries out fluorescence imaging is not also a lot.Therefore necessary exploitation can be navigated in mitochondria,
And the fluorescence probe of fluorescence imaging is carried out to viscosity-modifying in mitochondria.
The content of the invention
For current organic molecule fluorescence probe in mitochondria problem present in the detection of cell viscosity, the present invention
By MOLECULE DESIGN, having synthesized a class has the fluorescence probe of Mitochondrially targeted measure viscosity.
Present invention also offers a kind of simple and convenient process for preparing of above-mentioned fluorescence probe and the probe to solution and intracellular thin
Viscosity in born of the same parents' device microenvironment carries out the application of sensing detection.
To achieve the above object, the present invention is adopted the following technical scheme that.
A kind of Mitochondrially targeted fluorescence probe for determining viscosity, with the structure as shown in formula (I)：
In logical formula (I),
R1-R2It is each independently selected from H or C1-4Alkyl.
The one kind of described fluorescence probe in following compound：
CIV1：
CIV2：
Described fluorescence probe, using carbazole as fluorophor, using nitrogen cation as mitochondria positioning group.
A kind of preparation method of above-mentioned fluorescence probe, comprises the following steps：
(1) 2, substitution reaction occurs in acetonitrile for 3,3- tri-methyl indoles, bromoethane, generates compound 1, and reaction equation is：
(2) with 4- bromobenzaldehydes under the alkalescence condition that copper powder is present substitution occurs in nitrobenzene for carbazole or substituted carbazole instead
Should, compound 2 is generated, reaction equation is：
(3) with compound 2 addition-elimination reaction occurs in DMF for compound 1, generates the compound as shown in formula (I), instead
Ying Shiwei：
Above-mentioned preparation method, 2,3,3 ,-tri-methyl indole is 2 with bromoethane mol ratio：3；Carbazole or substituted carbazole and 4-
The mol ratio of bromobenzaldehyde is 1:2；The alkali is potassium carbonate, and the mol ratio of copper powder and potassium carbonate is 1:9；Compound 1 and chemical combination
The mol ratio of thing 2 is 1:1-1.5.
160-200 DEG C of heating response in above-mentioned preparation method, step (2)；Step (2) and step (3) course of reaction nitrogen
Protection.
A kind of above-mentioned fluorescence probe is used for the aqueous solution and biosystem detects the application of viscosity, and detection includes fluoroscopic examination,
Visual qualitative detection and cell imaging detection.
Above-mentioned application, excitation wavelength when fluorescence probe CIV1 is applied to solution is 470nm, exciting during applied to cell
Wavelength is 561nm, and photoluminescence peak is 628nm；Excitation wavelength when fluorescence probe CIV2 is applied to solution is 545nm, is applied to
Excitation wavelength during cell is 561nm, and photoluminescence peak is 579nm.
Electron-donating group is connected with fluorophor by singly-bound in the fluorescence probe of the present invention, when the molecule quilt of fluorescence probe
After photon excitation, the driving force of electronics redistribution causes the electron-donating group of excitation state to rotate, and photoinduction effect causes electric charge complete
Fully separating, so as to form the Intramolecular electron transfer state (TICT states) of torsion, this process does not launch fluorescence or luminous very weak.Point
Rotation is vulnerable to the influence of solvent viscosity in sub, and viscosity increase, Internal Rotations of Molecules is restricted, the energy for nonradiative transition
Carry out fluorescent emission is retained, fluorescence probe CIV gradually strengthens with the increase of solvent viscosity, fluorescence.
The present invention has advantages below：The synthetic method of fluorescence probe is simple；The sensitivity of viscosity probe is high, targeting
It is good.With the change of solution viscosity, with the naked eye just it is observed that the change of solution colour, along with equally can be with uviol lamp
It was observed that fluorescence color changes, it is a kind of viscosity fluorescence probe with the sensing function that adds lustre to.Based on its specificity and significantly
Color change, the reagent can carry out real-time qualitative as the indicator in the display aqueous solution with viscosity B coefficent in biological cell
And quantitative colorimetric determination.So, the present invention is that one kind is simple, quickly, sensitive viscosity specific detection agents, in biology
Molecular Detection field has broad application prospects.
Brief description of the drawings
Fig. 1 is fluorescence probe CIV1 in embodiment 11H NMR spectras；
Fig. 2 is fluorescence probe CIV2 in embodiment 21H NMR spectras；
Fig. 3 is changes of the fluorescence probe CIV1 and CIV2 with the increase fluorogram of viscosity；
Fig. 4 is the relation of fluorescence probe CIV1 and CIV2 fluorescence intensity and viscosity；
Fig. 5 be fluorescence probe CIV1 and CIV2 solution respectively in different viscosities solution color change；
Fig. 6 is fluorescence probe CIV1 and CIV2 solution respectively in different viscosities solution with the change of fluorescence color after ultra violet lamp
Change；Fig. 7 is the viscosity fluorescence imaging that fluorescence probe CIV1 is applied to carry out in cell；
Fig. 8 is the viscosity fluorescence imaging that fluorescence probe CIV2 is applied to carry out in cell.
Embodiment
With reference to embodiment and accompanying drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System.
The fluorescence probe CIV1 of embodiment 1 synthesis.
Fluorescence probe CIV1 synthetic route is as follows：
Fluorescence probe CIV1 synthesis step is as follows：
(1) by 2,3,3 ,-tri-methyl indole (2.0g, 12.6mmol, 1.0eq), bromoethane (2.1g, 18.9mmol, 1.5eq) is molten
In 2mL acetonitriles, 85 DEG C of heating reflux reaction 15h.Reaction solution is spin-dried for, suction filtration is depressurized, ether washing obtains compound 1.
(2) by carbazole (1.0g, 6mmol, 6.0eq), 4- bromobenzaldehydes (2.2g, 12mmol, 12.0eq), copper powder (64mg,
1mmol, 1.0eq), K2CO3(1.24g, 9mmol, 9.0eq) is dissolved in 10mL nitrobenzene, nitrogen protection, and 180 DEG C are heated to reflux instead
Answer 24h.Detected and reacted with TCL plates, after reaction completely, be cooled to room temperature, separated with silicagel column, silica gel particle size is
200-300 mesh, eluant, eluent proportioning is ethyl acetate/petroleum ether=1:50, product 2-1 is obtained, yield is 87%.
(3) by compound 2-1 (500mg, 1.84mmol, 1.0eq), compound 1 (540mg, 2mmol, 1.1eq) is dissolved in
In 6mL DMF, nitrogen protection, 90 DEG C of heating reflux reaction 6h are detected with TCL plates and reacted, after reaction completely, dichloromethane extraction
2 times, saturated common salt water washing 2-3 times, anhydrous sodium sulfate drying.Decompression is spin-dried for solvent and obtains crude product, and is divided with silicagel column
From silica gel particle size is 200-300 mesh, and eluant, eluent proportioning is ethanol/methylene=1:20, product CIV1 is obtained, yield is
47%.1H NMR(400MHz,DMSO-d6) δ 8.63 (d, J=16.3Hz, 1H), 8.58 (d, J=8.6Hz, 2H), 8.31 (d, J
=7.7Hz, 2H), 8.00 (dd, J=6.1,3.0Hz, 1H), 7.95 (t, J=4.3Hz, 2H), 7.93 (s, 1H), 7.85 (d, J
=16.4Hz, 1H), 7.71-7.65 (m, 2H), 7.57 (d, J=8.2Hz, 2H), 7.54-7.47 (m, 2H), 7.40-7.33 (m,
2H), (t, J=7.2Hz, the 3H) of 4.81 (q, J=7.1Hz, 2H), 1.87 (s, 6H), 1.51
The fluorescence probe CIV2 of embodiment 2 synthesis.
Fluorescence probe CIV2 synthetic route is as follows：
Fluorescence probe CIV2 synthesis step is as follows：
(1) the synthesis be the same as Example 1 of compound 1.
(2) by carbazole (1.0g, 6mmol, 1.0eq) and ZnCl2(2.45g, 18mmol, 3.0eq) is dissolved in 20mL nitro first
In alkane, nitrogen is protected, after being stirred several minutes under normal temperature, is injected tert-butyl chloride (1.7g, 18mmol, 3.0eq) with syringe
Above-mentioned reaction system, normal-temperature reaction 5h.The detection reaction of TCL plates, after reaction completely, adds water and is quenched, dichloromethane is extracted 2 times, satisfy
With brine It 2-3 times, anhydrous sodium sulfate drying.Decompression is spin-dried for solvent and obtains crude product, and is separated with silicagel column, silica gel
Granular size is 200-300 mesh, and eluant, eluent proportioning is ethyl acetate/petroleum ether=1:20, product 3 is obtained, yield is 40%.
By compound 3 (1.0g, 3.6mmol, 6.0eq), 4- bromobenzaldehydes (1.3g, 7.2mmol, 12.0eq), copper powder
(38mg, 0.6mmol, 1.0eq), K2CO3(740mg, 5.4mmol, 9.0eq) is dissolved in 6mL nitrobenzene, nitrogen protection, 180 DEG C
Heating reflux reaction 24h.Detected and reacted with TCL plates, after reaction completely, be cooled to room temperature, separated with silicagel column, silica gel
Grain size is 200-300 mesh, and eluant, eluent proportioning is ethyl acetate/petroleum ether=1:50, product 2-2 is obtained, yield is 37%.
(3) by compound 2-2 (450mg, 1.2mmol, 1.0eq), compound 1 (410mg, 1.5mmol, 1.3eq) is dissolved in
In 2mL DMF, nitrogen protection, 90 DEG C of heating reflux reaction 6h are detected with TCL plates and reacted, after reaction completely, dichloromethane extraction
2 times, saturated common salt water washing 2-3 times, anhydrous sodium sulfate drying.Decompression is spin-dried for solvent and obtains crude product, and is divided with silicagel column
From silica gel particle size is 200-300 mesh, and eluant, eluent proportioning is ethanol/methylene=1:20, product CIV2 is obtained, yield is
44%.1H NMR(400MHz,DMSO-d6) δ 8.61 (d, J=16.2Hz, 1H), 8.55 (d, J=8.5Hz, 2H), 8.35 (d, J
=1.5Hz, 2H), 8.01-7.97 (m, 1H), 7.94 (d, J=4.2Hz, 2H), 7.92 (s, 1H), 7.83 (d, J=16.3Hz,
1H), 7.69-7.65 (m, 2H), 7.55 (dd, J=8.7,1.7Hz, 2H), 7.50 (d, J=8.7Hz, 2H), 4.80 (d, J=
7.1Hz, 2H), 1.87 (s, 6H), 1.50 (t, J=7.2Hz, 3H), 1.44 (s, 18H)
Embodiment 2 fluorescence probe CIV1 and CIV2 fluorescence intensity with viscosity change.
Viscosity the fluorescence probe CIV1 and CIV2 that Example 1 is prepared with embodiment 2 are dissolved in dimethyl sulfoxide (DMSO) respectively
(DMSO) in, 1mmol/L storing solutions are made.100 μ L are taken out from storing solution to be added among 10mL centrifuge tube, are added different
The ethanol of ratio：Glycerine (ethanol：Glycerine=100:0,90:10,80:20,70:30,60:40,50:50,40:60,30:70,
20:80,10:90), be configured to different viscosities (3.2,3.7,5.0,9.9,15.0,29.0,56.1,115.2,206.0,
Solution 317.0mPas), the final concentration of 10 μm of ol/L of fluorescence probe；CIV1 using 470nm as exciting light, CIV2 using 545nm as
Its photoluminescent property of photo measure, fluorescence spectrum are excited as shown in figure 3, wherein (A) is CIV1 fluorescence patterns, (B) is CIV2 fluorograms
Spectrum.Using the common logarithm of viscosity as abscissa, mapped by ordinate of the common logarithm of fluorescence intensity, obtain Fig. 4.By Fig. 3 and Fig. 4
Data understand that fluorescence probe CIV1 and CIV2 gradually strengthens with the increase fluorescence of viscosity, in 3.2-317.0mPas viscosity models
In enclosing, fluorescence intensity and viscosity are each taken the logarithm linear positive correlation.
Visual retrieval of embodiment 3 fluorescence probe CIV1 and the CIV2 fluorescence probe to viscosity.
It is each in the fluorescence probe CIV1 storing solutions obtained from embodiment 1 to take out the sample that 40 μ L respectively are added to two 5mL
Among pipe, an addition 3mL ethanol, an addition 3mL 90% glycerite.Fluorescence probe CIV2 is equally operated.
It was observed that obvious color change occurs for solution：CIV1 solution colour becomes light orange (Fig. 5 A) from colourless, along with ultraviolet
The viscosity fluorescence probe of macroscopic sends red fluorescence (Fig. 6 A) under lamp；CIV2 solution colour becomes red from almost colourless
(Fig. 5 B), red fluorescence (Fig. 6 B) is sent along with the viscosity fluorescence probe of macroscopic under uviol lamp.Illustrate CIV1 and CIV2
It is a kind of fluorescence probe with the sensing function that adds lustre to, the qualitative judgement of solution viscosity change can be carried out by naked eyes.
The fluorescence probe CIV1 and CIV2 of embodiment 4 is determined to cell mitochondrial viscosity fluorescence imaging.
Fluorescence probe CIV1 of the present invention is applied in HeLa cells, cell is changed by the use of nystatin as stimulant
Viscosity in Mitochondria, and carry out fluorescence imaging, to study the change of fluorescence intensity before and after viscosity B coefficent, and is imaged, enters one
Step explanation probe can apply in cell mitochondrial carry out the application of fluorescence imaging to the change of its viscosity, obtain Fig. 7, specific behaviour
Make step as follows：
(1) 5 μM of fluorescence probe CIV1 DMSO solution is added in the nutrient solution for giving birth to HeLa cells in carbon dioxide culture
In case after culture 30min under the conditions of 37 degree, light field imaging obtains figure (A)；
(2) above-mentioned cell carries out fluorescence imaging (λ with Laser Scanning Confocal Microscopeex=561nm；λem=570-620nm), obtain figure (B)；
(3) will figure (A) with scheming that (B) is overlapping must scheme (C)；
(4) 10 μM of nystatin is added in the nutrient solution for giving birth to HeLa cells in CO2gas incubator in 37 degree of bars
Cultivated under part after 30min, add 5 μM of fluorescence probe CIV1 DMSO solution, and continue to be incubated 30min, light field imaging obtains figure
(D)；
(2) above-mentioned cell carries out fluorescence imaging (λ with Laser Scanning Confocal Microscopeex=561nm；λem=570-620nm), obtain figure (E)；
(3) will figure (D) with scheming that (E) is overlapping must scheme (F).
Repeat the above steps, difference is, fluorescence probe is CIV2, fluorescence imaging condition is λex=561nm, λem
=570-620nm, obtains Fig. 8.
As Figure 7-8, under normal cultivation conditions, the intracellular viscosity of HeLa is smaller, and fluorescence is weaker；Add coban thorn
Swash cell, obtained stronger fluorescence, illustrate that cell viscosity increases, the enhancing of probe illumination effect；Using fluorescence probe CIV1 and
CIV2 fluorescence intensity changes in the cell, being capable of indicator cells viscosity B coefficent.
Claims (8)
1. a kind of Mitochondrially targeted fluorescence probe for determining viscosity, it is characterised in that with the structure as shown in formula (I)：
In logical formula (I),
R1-R2It is each independently selected from H or C1-4Alkyl.
2. fluorescence probe according to claim 1, it is characterised in that one in following compound：
CIV1：
CIV2：
3. fluorescence probe according to claim 1, it is characterised in that using carbazole as fluorophor, using nitrogen cation as line
Plastochondria seeking group.
4. a kind of preparation method of fluorescence probe as claimed in claim 1, it is characterised in that comprise the following steps：
(1) 2, substitution reaction occurs in acetonitrile for 3,3- tri-methyl indoles, bromoethane, generates compound 1, and reaction equation is：
(2) with 4- bromobenzaldehydes under the alkalescence condition that copper powder is present substitution occurs in nitrobenzene for carbazole or substituted carbazole instead
Should, compound 2 is generated, reaction equation is：
(3) with compound 2 addition-elimination reaction occurs in DMF for compound 1, generates the compound as shown in formula (I), instead
Ying Shiwei：
5. preparation method according to claim 4, it is characterised in that 2,3,3 ,-tri-methyl indole and bromoethane mol ratio
For 2：3；The mol ratio of carbazole or substituted carbazole and 4- bromobenzaldehydes is 1:2；The alkali is potassium carbonate, and copper powder and potassium carbonate rub
You are than being 1:9；Compound 1 is 1 with the mol ratio of compound 2:1-1.5.
6. preparation method according to claim 4, it is characterised in that 160-200 DEG C of heating reacts in step (2)；
Step (2) is protected with step (3) course of reaction nitrogen.
7. the fluorescence probe described in a kind of claim 1 is used for the aqueous solution and biosystem detects the application of viscosity, its feature exists
In the detection includes fluoroscopic examination, visual qualitative detection and cell imaging detection.
8. application according to claim 7, it is characterised in that excitation wavelength when fluorescence probe CIV1 is applied to solution is
470nm, excitation wavelength during applied to cell is 561nm, and photoluminescence peak is 628nm；When fluorescence probe CIV2 is applied to solution
Excitation wavelength be 545nm, excitation wavelength during applied to cell is 561nm, and photoluminescence peak is 579nm.
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484590A (en) * | 2018-05-18 | 2018-09-04 | 安徽大学 | A kind of two-photon viscosity fluorescence probe and its preparation method and application based on carbazole |
| CN108516950A (en) * | 2018-05-15 | 2018-09-11 | 湖南大学 | Subcellular organelle viscosity probe based on tetraphenyl ethylene and the preparation method and application thereof |
| CN108623510A (en) * | 2018-04-26 | 2018-10-09 | 济南大学 | A kind of the viscosity fluorescence probe and its synthetic method of targetted mitochondria near infrared emission |
| CN108715760A (en) * | 2018-06-22 | 2018-10-30 | 济南大学 | A kind of fluorescence probe of detection viscosity and its synthetic method and application |
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| CN110129037A (en) * | 2019-06-04 | 2019-08-16 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting viscosity |
| CN110305055A (en) * | 2019-07-12 | 2019-10-08 | 济南大学 | A kind of fluorescence probe and the preparation method and application thereof identifying mitochondria viscosity |
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| CN113004276A (en) * | 2021-03-15 | 2021-06-22 | 天津理工大学 | Fluorescent probe for positioning mitochondria and preparation method and application thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140212359A1 (en) * | 2013-01-29 | 2014-07-31 | The Hong Kong University Of Science And Technology | Photostable aie luminogens for specific mitochondrial imaging and its method of manufacturing thereof |
| CN105733564A (en) * | 2016-04-12 | 2016-07-06 | 郑州大学 | Mitochondrially-targeted pH-sensitive ratio-type fluorescent probe and preparation method and application thereof |
| CN106588750A (en) * | 2016-12-07 | 2017-04-26 | 山东大学 | Disposable and rapid octadecyl-chain-containing targeting mitochondrion fluorescent probe and application thereof |
-
2017
- 2017-04-28 CN CN201710291844.XA patent/CN107089937B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140212359A1 (en) * | 2013-01-29 | 2014-07-31 | The Hong Kong University Of Science And Technology | Photostable aie luminogens for specific mitochondrial imaging and its method of manufacturing thereof |
| CN105733564A (en) * | 2016-04-12 | 2016-07-06 | 郑州大学 | Mitochondrially-targeted pH-sensitive ratio-type fluorescent probe and preparation method and application thereof |
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