CN113004276A - Fluorescent probe for positioning mitochondria and preparation method and application thereof - Google Patents
Fluorescent probe for positioning mitochondria and preparation method and application thereof Download PDFInfo
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- CN113004276A CN113004276A CN202110273831.6A CN202110273831A CN113004276A CN 113004276 A CN113004276 A CN 113004276A CN 202110273831 A CN202110273831 A CN 202110273831A CN 113004276 A CN113004276 A CN 113004276A
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Abstract
The invention provides a mitochondrial positioning fluorescent probe and a preparation method and application thereof. The probe is prepared from pyrene formaldehyde and 2, 3-dimethyl quinolizine, and has the advantages of simple steps, convenient purification, high yield and structural formula
The probe of the invention is a typical D-pi-A system formed by pyrene and 2, 3-dimethyl quinolizine through an olefinic bond, and the pyrene is a better large conjugated plane frame structure, so the probe has larger Stokes shift and longer emission wavelength, and can effectively reduce the signal-to-noise ratio; the kit has specific response to viscosity, high detection sensitivity, high optical stability, wide pH application range and quick detection; and the probe toolHas good cell membrane permeability and can realize the detection of the viscosity in the mitochondria of the cell.
Description
Technical Field
The invention relates to the technical field of molecular fluorescent probes, in particular to a preparation method and application of a mitochondrial positioning fluorescent probe.
Background
Mitochondria are important organelles in cells, and play a key role in the metabolism of cells and the supply of ATP to cells. Mitochondrial dysfunction can affect normal vital activities of cells. Therefore, monitoring the mitochondria themselves and small changes in the internal environment and timely treatment of mitochondria under abnormal conditions are of great value. For chemical researchers, designing and synthesizing novel fluorescent probes to monitor mitochondria and change of microenvironment inside mitochondria are very critical problems. Viscosity, an important factor of internal microenvironment, is a key influencing factor for controlling substance transfer, signal transduction and interaction between biological macromolecules. It is reported in the literature that normal cells have a cytoplasmic viscosity of about 1-2cP, while damaged cells have a significant increase in cytoplasmic viscosity, which can reach 140cP or even higher. Abnormal changes in intracellular viscosity levels have been shown to be associated with a number of diseases, such as atherosclerosis, hypertension, diabetes, parkinson's disease, alzheimer's disease and cellular malignancies. Therefore, maintaining normal intracellular viscosity levels is critical for normal physiological processes. The viscosity of each region in the cell is highly uneven, and in order to better monitor the local change of the viscosity in the cell, the monitoring of the viscosity in different organelles is particularly important. In particular, mitochondria play an important role in maintaining many physiological functions of the human body. If the mitochondrial viscosity is different from the normal level, it will cause the change of the mitochondrial network tissue and the metabolite diffusion rate, and even cause cell damage and apoptosis seriously. Therefore, it is of great interest to develop a viscosity sensor with membrane permeability to monitor changes in viscosity within the mitochondria of living cells.
To date, there have been some common viscosity measuring instruments and analysis methods including capillary viscometers, rotational viscometers, and electrochemical analysis, but none of them is suitable for measuring the viscosity in living cells. In recent years, fluorescent probe technology has been widely used for the development of viscosity sensitive probes due to its advantages of high sensitivity, high temporal and spatial resolution, real-time in situ and non-invasive detection. Therefore, the development of a simple and effective fluorescent probe which can locate mitochondria and realize the detection of the viscosity of mitochondria is of great significance.
Disclosure of Invention
It is a first object of the present invention to provide a fluorescent probe that can localize mitochondria and has high selectivity and high sensitivity to viscosity.
It is a second object of the present invention to provide the above fluorescent probe, which has a Stokes shift of more than 120nm and is effective in reducing the signal-to-noise ratio.
The third purpose of the invention is to provide the application of the fluorescent probe in detecting the cell viscosity.
The fourth purpose of the invention is to provide a synthesis method of the fluorescent probe, which has the advantages of easily available raw materials, simple synthesis steps and high yield.
To achieve the above object, the solution adopted by the present application is as follows:
a fluorescent probe for locating mitochondria, the chemical name is 3-methyl-2- (2-pyrene-4-vinyl) -quinolizine chloride, PyQz for short, and the structural formula is as follows:
the preparation method for the mitochondrial positioning fluorescent probe comprises the following specific synthetic route:
the preparation method for the mitochondrial positioning fluorescent probe comprises the following specific steps:
1) dissolving pyrene formaldehyde and 2, 3-dimethyl quinolizine chloride in acetonitrile solution, and adding piperidine; heating in a dark oil bath, reacting at 80-90 deg.C for 48-72 hr, cooling to room temperature, and precipitating;
2) and (3) carrying out suction filtration on the precipitated precipitate, and recrystallizing by using an acetonitrile solvent to obtain the target probe PyQz.
Preferably, the molar ratio of the pyrene formaldehyde, the 2, 3-dimethyl quinolizine chloride salt and the piperidine in the step 1) is 1: 1.
preferably, the weight ratio of the total amount of pyrene formaldehyde and 2, 3-dimethyl quinolizine chloride in the step 1) to the acetonitrile solvent in the step 2) is 1: 10-12.
The invention relates to a preparation method and application of a mitochondrial positioning fluorescent probe, wherein the structure is characterized in that: the probe is formed by connecting pyrene and 2, 3-dimethyl quinolizine through an olefinic bond, and a typical Donor (Donor) -pi-Acceptor (Acceptor) system is formed; because pyrene is a good large conjugated plane frame structure, the probe has large Stokes displacement and long emission wavelength, and the signal-to-noise ratio is effectively reduced; and due to the introduction of pyrene, the influence of solvents with different polarities on the absorption spectrum and the emission spectrum of the probe is effectively reduced, which is very significant for the viscosity probe.
The preparation method and the application of the fluorescent probe for positioning mitochondria have the following viscosity detection mechanism: when the probe is in a non-viscous or low viscosity solution, the rotation speed is relatively fast and the excited state energy is attenuated by non-radiative pathways, so that the probe exhibits weaker fluorescence. While in a viscous solution, the rotational speed is limited, reducing the attenuation of excited state energy through non-radiative pathways, and restoring probe fluorescence. The fluorescent probe has quick response to viscosity and high selectivity, and can realize detection of viscosity in mitochondria.
The invention has the advantages and beneficial effects that:
the fluorescent probe for positioning mitochondria, provided by the invention, can target and mark mitochondria; the nano-silver nanoparticle has specific response to viscosity, high sensitivity, good optical stability and quick response; the probe has good biological membrane permeability, large Stokes displacement and low signal-to-noise ratio; the detection of mitochondrial viscosity within cells can be achieved. Meanwhile, the preparation method of the probe provided by the invention is simple and feasible, low in cost and obvious in economic and technical effects.
Drawings
FIG. 1 shows fluorescence emission spectra of probes in different viscosity systems (emission wavelength on abscissa and fluorescence intensity on ordinate).
FIG. 2 is a probe pair viscosity selective fluorescence spectrum (emission wavelength on the abscissa and fluorescence intensity on the ordinate).
FIG. 3 is a cell imaging application of the probe.
FIG. 4 shows localization experiments of probes in mitochondria.
Detailed Description
In order to better understand the technical solution of the present invention, the following is further detailed by specific examples:
1) synthesis of Probe PyQz
Pyrenecarboxaldehyde (350mg,1.5mol) and 2, 3-dimethyl quinolizine chloride (300mg,1.5mol) and 20. mu.L piperidine were added to a round bottom flask containing 10mL and placed in a 90 ℃ oil bath and stirred away from light for 72 h. And after the reaction is finished, cooling the system to room temperature, separating out an orange precipitate, performing suction filtration, and then recrystallizing with acetonitrile to obtain the target product PyQz. The yield was 447mg, 71%. The melting point is more than 300 ℃; high Resolution Mass Spectrometry (HRMS) theoretical M/z [ M-Cl-]+370.1612; calculating to obtain [ M-Cl-]+370.1590; the nuclear magnetic results of the probe are as follows:1H NMR(DMSO-d6,400MHz,ppm)δ9.03(d,2H,J＝8.0Hz),8.98(d,1H,J＝8.0Hz),8.87(s,1H),8.83(d,1H,J＝8.0Hz),8.72(d,1H,J＝8.0Hz),8.37(d,2H,J＝8.0Hz),8.32(d,2H,J＝8.0Hz),8.27(d,1H,J＝8.0Hz),8.19(dd,3H,J＝12.0,8.0Hz),8.10(t,1H,J＝8.0Hz),7.89(t,1H,J＝8.0Hz)7.69(d,1H,J＝16.0Hz),2.62(s,3H)；13C NMR(DMSO-d6,100MHz,ppm)δ146.19,141.82,136.34,135.96,135.49,135.33,133.38,132.95,131.86,131.35,130.59,130.17,129.67,129.51,128.48,127.95,127.43,127.34,126.99,126.68,125.58,125.10,124.72,124.02,123.88,123.72,121.16,17.92.
2) fluorescence spectra of probe PyQz in different viscosity systems
PyQz prepared as described above was made to 5X 10 in dimethyl sulfoxide (DMSO)-3The mother liquor of M is ready for use;
3mL of solvents of glycerol and water with different proportions (the mass ratio of the glycerol to the water is 0: 100, 10: 90, 20: 80, 30: 70, 40: 60, 50: 50, 60: 40, 70: 30, 80: 20, 85:15, 90: 10, 95: 5) are respectively taken in the test solution, probe mother solution (the final concentration of the probe is 5 mu M) is added, and fluorescence test is carried out (the excitation wavelength is 450nm, and the slit width is 5 nm). The fluorescence intensity in each system was measured, and as shown in FIG. 1, it was found from FIG. 1 that the fluorescence intensity gradually increased with the increase in viscosity.
3) Probe-pair viscosity selective fluorescence spectroscopy
Common metal ions, reactive nitrogen atoms, ROS and thiols were selected as interfering ions for studying the sensitivity of probes to viscosity, including Mg2+，Ca2+，Cu2+，Fe2+，Zn2+，Ag+，Ni2+，Hg2+，ONOO-，NO2 -，HClO，H2O2TBHP, GSH, Hcy and Cys. The test solution was 3mL of an aqueous solution of the probe, and the above-mentioned substances were added to the solution (final concentration of the probe was 5. mu.M, and final concentration of the above-mentioned substances was 50. mu.M), respectively, and fluorescence spectrum scanning was performed (excitation wavelength: 450nm, slit width: 5 nm). As shown in FIG. 2, when the above-mentioned substance was added to the probe PyQz aqueous solution, there was no significant change in fluorescence intensity; however, the fluorescence intensity of the probe was significantly enhanced in 95% glycerol. The experimental result shows that the probe has specific responsiveness to viscosity.
4) Imaging of probes PyQz in cells
HeLa cells of appropriate density were seeded into 6-well dishes containing 5% CO at 37 deg.C2Culturing in an incubator; after the cells adhere to the wall, adding a fluorescent probe PyQz (the concentration is 0.5 mu M) into the first group, incubating for half an hour, and then performing fluorescence imaging (the excitation wavelength is 559nm, and the collection band is 575 and 675 nm); the second group was incubated for half an hour with the addition of the viscosity stimulant Monensin (Monensin, 10 μ M), followed by the addition of probe PyQz (0.5 μ M), and then incubated for half an hour for fluorescence imaging. As shown in FIG. 3, the analysis and comparison showed that the fluorescence intensity of the cell containing only the probe was very weak without external stimulation; however, under the stimulation of monensin, the cells containing the probe emit strong fluorescence(ii) a Thus, it was demonstrated that the fluorescent probe of the present invention enables detection of a change in intracellular viscosity.
5) Co-localization of mitochondria by probe and commercial kit
HeLa cells of appropriate density were seeded into 35mm petri dishes at 37 ℃ with 5% CO2Culturing in an incubator; after the cells adhere to the wall, the fluorescent probe PyQz and the commercial mitochondrial kit Mito-Tracker Green are added into the culture dish at the same time, so that the final concentrations of the probe and the mitochondrial kit are both 0.2 mu M. After half an hour of incubation, the medium was discarded, the cells were rinsed 3 times with 10mM PBS (pH 7.4) buffer, followed by fluorescence imaging (probe red channel, excitation 559nm, collection 575 675 nm; mitochondrial kit red channel, excitation 488nm, collection 500 545nm), the results are shown in FIG. 4. Wherein a) is the fluorescence of a mitochondrion kit Mito-Tracker Green in a Green channel; b) fluorescence in the red channel for probe PyQz; c) is a superimposed graph of a) and b); d) is a superposition of c) and the bright field; e) a Mito-Tracker Green fluorescence intensity scattergram of the probe and mitochondrial kit is obtained; f) the fluorescence intensity line graph of the probe and mitochondrial kit Mito-Tracker Green region of interest is shown. As can be seen from FIG. 4, the light-emitting positions of the probe and Mito-Tracker Green were highly coincident, and the co-localization coefficient was 0.98. It was demonstrated that the probe PyQz was mainly concentrated in mitochondria, and thus the probe of the present invention can be used for measuring the mitochondrial viscosity in cells.
Claims (7)
1. A fluorescent probe for mitochondrial localization, comprising: the chemical name of the probe is 3-methyl-2- (2-pyrene-4-vinyl) -quinolizine chloride, and the structure of the probe is shown as follows:
2. a method for preparing a fluorescent probe for mitochondrial localization according to claim 1, comprising: the specific preparation route is as follows:
3. the method of claim 2, wherein the method comprises the steps of: the method comprises the following specific steps:
1) dissolving pyrene formaldehyde and 2, 3-dimethyl quinolizine chloride in acetonitrile solution, and adding piperidine; heating in a dark oil bath, reacting at 80-90 deg.C for 48-72 hr, cooling to room temperature, and precipitating;
2) and (3) carrying out suction filtration on the precipitated precipitate, and recrystallizing by using an acetonitrile solvent to obtain the target probe PyQz.
4. The method for preparing a mitochondrial localization fluorescent probe according to claim 3, characterized in that: in the step 1), the molar ratio of the pyrene formaldehyde, the 2, 3-dimethyl quinolizine chloride and the piperidine is 1:1: 1.
5. The method for preparing a mitochondrial localization fluorescent probe according to claim 3, characterized in that: the weight ratio of the total amount of the pyrene formaldehyde and the 2, 3-dimethyl quinolizine chloride in the step 1) to the acetonitrile solvent in the step 2) is 1: 10-12.
6. Use of the fluorescent probe for mitochondrial localization according to claim 1 for the preparation of detection solutions and reagents for viscosity in mitochondria.
7. Use of a fluorescent probe for mitochondrial localization according to claim 6 wherein: the method is used for detecting the viscosity in a physiological environment or in cell mitochondria.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107089937A (en) * | 2017-04-28 | 2017-08-25 | 济南大学 | Mitochondrially targeted fluorescence probe for determining viscosity and its preparation method and application |
| CN108822031A (en) * | 2018-08-24 | 2018-11-16 | 济南大学 | A kind of red transmitting fluorescence probe of two-photon detecting mitochondria |
| CN110078714A (en) * | 2019-05-16 | 2019-08-02 | 济南大学 | A kind of two-photon viscosity probe and its preparation method and application positioning mitochondria |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107089937A (en) * | 2017-04-28 | 2017-08-25 | 济南大学 | Mitochondrially targeted fluorescence probe for determining viscosity and its preparation method and application |
| CN108822031A (en) * | 2018-08-24 | 2018-11-16 | 济南大学 | A kind of red transmitting fluorescence probe of two-photon detecting mitochondria |
| CN110078714A (en) * | 2019-05-16 | 2019-08-02 | 济南大学 | A kind of two-photon viscosity probe and its preparation method and application positioning mitochondria |
Non-Patent Citations (1)
| Title |
|---|
| SATO, KIYOSHI等: "Synthesis of 6-methylisoquinolino[7,8-a]quinolizinium salt: efficient synthesis of 2-(2-arylvinyl)quinolizinium salts by Knoevevagel condensation using acetonitrile as a solvent and the photocyclization", 《HETEROCYCLES》 * |
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