CN110455430B - Mitochondrion-targeted fluorescence lifetime temperature sensor and preparation method and application thereof - Google Patents
Mitochondrion-targeted fluorescence lifetime temperature sensor and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a fluorescence lifetime temperature sensor of a targeted mitochondrion, which is formed by covalently coupling a gold nanocluster with a surface protected by a ligand and a triphenylphosphine compound or a derivative thereof; wherein the ligand is glutathione. The sensor has long fluorescence lifetime and strong light stability, and can accurately measure the temperature of mitochondria by using the fluorescence lifetime. The invention also discloses a preparation method and application of the fluorescence lifetime temperature sensor.
Description
Technical Field
The invention relates to the field of nano thermometers. More particularly, relates to a fluorescence lifetime temperature sensor targeting mitochondria and a preparation method and application thereof.
Background
The temperature of the mitochondria plays an important role in the metabolism of the cell. Accurate measurement of mitochondrial temperature can help people understand the physiological processes of cells and reveal the pathogenesis of certain diseases. The measurement of mitochondrial temperature by fluorescence techniques is of great advantage. In which concentration interference of fluorescent substances and fluctuation of light source signals can be effectively avoided by using the fluorescence lifetime, compared to the method of fluorescence intensity. In the existing probe for measuring the mitochondrial temperature by using the fluorescence lifetime, the lifetime of the probe is in the same order of magnitude as that of cell autofluorescence, and the signal interference is large. Meanwhile, most probes are organic matters, the photobleaching effect is obvious, and the probes are not suitable for long-time observation.
In view of this problem, it is desirable to provide a fluorescence lifetime temperature sensor having a long fluorescence lifetime and high light stability.
Disclosure of Invention
The first objective of the present invention is to provide a mitochondrial-targeted fluorescence lifetime temperature sensor, which can be targeted to mitochondria, has long fluorescence lifetime and strong light stability, and can accurately measure the temperature of mitochondria by using the fluorescence lifetime.
The second purpose of the invention is to provide a preparation method of the fluorescence lifetime temperature sensor targeting mitochondria.
The third purpose of the invention is to provide the application of the fluorescence lifetime temperature sensor targeting mitochondria.
In order to achieve the first purpose, the invention adopts the following technical scheme:
a fluorescence lifetime temperature sensor targeting mitochondria is formed by covalently coupling a gold nanocluster with a surface protected by a ligand and a triphenylphosphine compound or a derivative thereof;
wherein the ligand is glutathione. The fluorescence lifetime of the gold nanocluster prepared by the method is about 1 mu s longer than that of the gold nanocluster synthesized by other ligands.
Alternatively, the triphenylphosphine compound or derivative thereof is 4-carboxybutyltriphenylphosphonium bromide. At this time, the obtained temperature sensor has a good positioning effect.
Optionally, the ligand-protected gold nanoclusters have an average diameter of 2nm or less.
In order to achieve the second purpose, the invention adopts the following technical scheme:
a preparation method of a fluorescence lifetime temperature sensor targeting mitochondria comprises the following steps:
mixing MES solution of triphenylphosphine compound or derivative thereof, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and N-hydroxysulfonic succinimide sodium salt, adding aqueous solution of gold nanoclusters with surfaces protected by ligands after reaction and activation, reacting in a dark place, and dialyzing to obtain the fluorescence lifetime temperature sensor.
Optionally, the preparation of the surface ligand-protected gold nanoclusters comprises the steps of:
and (2) uniformly mixing the aqueous solution of chloroauric acid and glutathione at room temperature, stirring at 70-80 ℃ until the solution is clear and light yellow, and dialyzing to obtain the gold nanocluster with the surface protected by the ligand. The gold nanoclusters prepared by the method have long fluorescence life and can reach microsecond level under the condition of a physiological temperature zone. Optionally, the stirring time is 18h or more.
Optionally, the concentration of the triphenylphosphine compound or the derivative thereof in the MES solution is 6-10 mg/mL.
To achieve the third object, the present invention provides the use of the fluorescence lifetime temperature sensor as defined in the first object above for mitochondrial temperature measurement.
Optionally, the applying comprises:
testing the fluorescence life of the fluorescence life temperature sensor in the range of 0-370 mu s by adopting laser with the wavelength of 390nm, and establishing an in-vitro working curve by taking the temperature as an abscissa and the fluorescence life value of the sensor as an ordinate; with increasing temperature, the non-radiative transition increases, resulting in a decrease in the fluorescence lifetime of the fluorescence lifetime sensor;
the fluorescence lifetime temperature sensor is positioned on mitochondria of which the temperature is to be measured in a targeted manner, a fluorescence lifetime imaging microscope is adopted to test the lifetime of the positioned sensor to obtain a fluorescence lifetime image, the temperature distribution of the mitochondria is determined according to the signal value in the fluorescence lifetime image, and then the specific temperature corresponding to the fluorescence lifetime value is obtained according to the in vitro working curve. Specifically, in the fluorescence lifetime image, a signal value with a short lifetime represents that the temperature at the point is high, and a signal value with a long lifetime represents that the temperature at the point is low. And then the temperature distribution of mitochondria is obtained through the signal value in the fluorescence lifetime imaging graph, the fluorescence lifetime value of each specific pixel point is analyzed, and the specific temperature of the point can be obtained according to the in vitro working curve.
Further, the method for targeting and positioning the fluorescence lifetime temperature sensor to the mitochondria to be measured in temperature comprises the following steps: after incubating the fluorescence lifetime temperature sensor into the cell, the sensor will target mitochondria.
Optionally, the fluorescence lifetime imaging microscope uses a femtosecond laser with a wavelength of 402nm, a laser repetition frequency of 80MHz, and a filter of 582/75 nm.
The invention has the following beneficial effects:
the fluorescence lifetime temperature sensor of the targeted mitochondria provided by the invention has an ultra-long fluorescence lifetime, can effectively reduce the interference of autofluorescence of organisms and improve the signal-to-noise ratio; the fluorescent material has good light stability, still has strong fluorescent signals under long-time observation, and is suitable for long-time observation of samples; the sensor has higher temperature sensitivity to temperature, and the fluorescence lifetime of the sensor can be used for accurately measuring the temperature of mitochondria.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
Fig. 1 shows a schematic design diagram of a fluorescence lifetime temperature sensor targeting mitochondria in an embodiment of the invention.
FIG. 2 shows a transmission electron microscope image of the gold nanowire with glutathione covalently bound on the surface prepared in example 1.
FIG. 3 shows a transmission electron micrograph of m-AuNCs prepared in example 1.
FIG. 4 is a graph showing the Zeta potential changes of AuNCs before and after modification of TPP in example 1.
FIG. 5 is a graph showing the trend of the fluorescence intensity of m-AuNCs prepared in example 1 with respect to temperature.
FIG. 6 is a graph showing the change of the fluorescence lifetime of m-AuNCs prepared in example 1 with temperature.
FIG. 7 shows the operating curves of the fluorescence lifetime versus temperature plots for m-AuNCs prepared in example 1.
FIG. 8 is a graph showing fluorescence intensity, spectrum and lifetime of m-AuNCs prepared in example 1 after entering cells.
FIG. 9 shows the co-localization of m-AuNCs prepared in example 3 with commercial mitochondrial dyes.
FIG. 10 shows the mitochondrial lifetime distribution of m-AuNCs prepared in example 3.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The design principle of the fluorescence lifetime temperature sensor targeting mitochondria in the embodiment of the invention is shown in fig. 1.
Example 1
A preparation method of a fluorescence lifetime temperature sensor targeting mitochondria comprises the following steps:
1) dissolving 0.1M chloroauric acid solution in 5mL water, adding 42mg glutathione, stirring at room temperature for 30min, heating to 70 deg.C, stirring overnight to obtain AuNCs, and Transmission Electron Microscopy (TEM) image is shown in FIG. 2;
2) the synthesized AuNCs were purified by dialysis (5000D, 24 h). Placing the purified AuNCs in a refrigerator at 4 ℃ for later use;
3) dissolving 30mg of 4-carboxybutyltriphenylphosphonium bromide (TPP) in 5mL of MES solution, and adding 25mg of EDC and 10mg of NHS; after 4h of reaction activation, adding 4mL of AuNCs solution, reacting for 20 h under the condition of keeping out of the sun, dialyzing the product for 24h by using a 5000D dialysis bag, and changing water every 6h to obtain m-AuNCs (namely the sensor), storing the m-AuNCs in a refrigerator at 4 ℃, wherein the color transmission electron microscope image of the prepared m-AuNCs is shown in figure 3; by means of Zeta potential characterization, before and after modification, the Zeta potential of the gold nanoclusters is changed from negative to positive, as shown in FIG. 4;
5) the obtained m-AuNCs were excited with a laser of 400nm, and the maximum emission wavelength of the obtained fluorescence was 600 nm. When the test temperature is increased from 10 ℃ to 60 ℃, the fluorescence intensity changes, and the fluorescence intensity is known to decrease with the increase of the temperature, as shown in fig. 5;
6) the fluorescence lifetime spectrometer was used for testing, and the obtained m-AuNCs fluorescence lifetime gradually decreased as the temperature increased from 10 ℃ to 50 ℃, as shown in FIG. 6. And establishing a working curve, as shown in fig. 7;
7) after co-incubation of the obtained m-AuNCs and L929 cells for 4 hours, a laser confocal imaging picture is utilized, and after co-staining of the m-AuNCs and commercial mitochondrial dyes, the m-AuNCs are found to be positioned in mitochondria, and a fluorescence lifetime picture is obtained by utilizing fluorescence lifetime imaging. The fluorescence lifetime map was compared with the fluorescence intensity map, and it was found that the fluorescence lifetime signal originated from the signal of the fluorescent probe, and the comparison data is shown in fig. 8. In FIG. 8, a is an image of fluorescence intensity of m-AuNCs, b is an image of fluorescence lifetime of m-AuNCs, c is an image of bright field, and d is an image of fluorescence spectrum of m-AuNCs. Wherein, the graph a and the graph d are imaged by using the fluorescence intensity and the spectrum signal of m-AuNCs, the graph b is imaged by using the fluorescence lifetime, the graph c is imaged by using bright field illumination, the cell shapes in the four graphs are the same, the signal overlapping degree is higher, and the measured fluorescence lifetime signal is derived from the fluorescence of the probe.
8) And (3) utilizing a fluorescence lifetime imaging device to image the lifetime of the cells to obtain a lifetime image. From the relationship between the lifetime and the temperature, it was found that the average temperature of the cells at this time was 37 ℃.
Example 2
A preparation method of a fluorescence lifetime temperature sensor of a targeted mitochondrion.
1) Dissolving 0.1M chloroauric acid solution in 5mL of water, adding 42mg glutathione, stirring at room temperature for 30min, heating to 70 ℃, and stirring overnight to obtain AuNCs;
2) the synthesized AuNCs were purified by dialysis (5000D, 24 h). Placing the purified AuNCs in a refrigerator at 4 ℃ for later use;
3) 40mg of TPP was dissolved in 5mL of MES solution, and 20mg of EDC and 5mg of NHS were added. After reaction activation for 3h, adding 3mL of AuNCs solution, reacting for 18h under the condition of keeping out of the sun, dialyzing the product for 24h by using a 5000D dialysis bag, and changing water every 6h to obtain m-AuNCs, and storing in a refrigerator at 4 ℃; by means of Zeta potential representation, before and after modification, the Zeta potential of the gold nanocluster is changed from negative to positive;
5) exciting the obtained m-AuNCs by using 400nm laser, wherein the maximum emission wavelength of the obtained fluorescence is 600m, and the fluorescence intensity is reduced along with the increase of the temperature;
6) the fluorescence lifetime spectrometer is used for testing, and the obtained m-AuNCs fluorescence lifetime is reduced along with the increase of temperature. Respectively testing the fluorescence lives of the m-AuNCs at 10 ℃, 20 ℃, 30 ℃, 40 ℃ and 50 ℃, drawing a working curve of the obtained fluorescence lives, and establishing the working curve as described in example 1;
7) after co-incubation of the obtained m-AuNCs and L929 cells for 4 hours, co-staining the m-AuNCs and commercial mitochondrial dye by using a laser confocal imaging picture to find that the m-AuNCs are positioned in mitochondria; and (4) obtaining a fluorescence lifetime map by using fluorescence lifetime imaging. The results are similar to those of example 1.
Example 3
A preparation method of a fluorescence lifetime temperature sensor targeting mitochondria comprises the following steps:
1) 0.1M chloroauric acid solution was dissolved in 5mL of water, 42mg of glutathione was added, and after stirring at room temperature for 30min, the temperature was raised to 70 ℃ and the mixture was stirred overnight. Obtaining AuNCs;
2) purifying the synthesized AuNCs by dialysis (5000D, 24h), and placing the purified AuNCs in a refrigerator at 4 ℃ for later use;
3) dissolving 50mg of TPP in 5mL of MES solution, adding 30mg of EDC and 15mg of NHS, reacting and activating for 6h, adding 5mL of AuNCs solution, reacting for 24h under a dark condition, dialyzing the product for 24h by using a 5000D dialysis bag, and changing water every 6h to obtain m-AuNCs, and storing in a refrigerator at 4 ℃; by means of Zeta potential representation, before and after modification, the Zeta potential of the gold nanocluster is changed from negative to positive;
5) exciting the obtained m-AuNCs by using 400nm laser, wherein the maximum emission wavelength of the obtained fluorescence is 600m, and the fluorescence intensity is reduced along with the increase of the temperature;
6) the fluorescence lifetime spectrometer is used for testing, and the obtained m-AuNCs fluorescence lifetime is reduced along with the increase of temperature. Respectively testing the fluorescence lives of the m-AuNCs at 10 ℃, 20 ℃, 30 ℃, 40 ℃ and 50 ℃, drawing a working curve of the obtained fluorescence lives, and establishing the working curve as described in example 1;
7) co-incubating the obtained m-AuNCs and L929 cells for 4 hours, and obtaining a fluorescence intensity, a spectrum and a life chart by utilizing a laser confocal imaging chart; after co-staining of m-AuNCs with commercial mitochondrial dyes, m-AuNCs were found to localize within the mitochondria with co-localization coefficients as high as 0.92, as shown in FIG. 9. The high co-localization coefficient shows that the synthesized gold nanocluster has the function of targeting mitochondria and can target the mitochondria through electrostatic adsorption after entering cells. And then, obtaining a fluorescence lifetime graph of the sample by using fluorescence lifetime imaging, and obtaining the average temperature of the sample through the relationship between the lifetime and the temperature. FIG. 10 shows the lifetime distribution of m-AuNCs prepared in mitochondria. According to the calculation formula of relative sensitivity of temperature, the relative sensitivity of temperature at this time is 3%.
The above examples 1-3 show that the synthesized m-AuNCs have the function of targeting mitochondria, and the service life is in microsecond order and is obviously different from the service life of cell autofluorescence (nanosecond order). Can effectively avoid the interference of cell autofluorescence. And the synthesized m-AuNCs have lower cytotoxicity and bleaching resistance, and are suitable for detecting the temperature of cell mitochondria.
Comparative example 1
Example 1 was repeated except that "AuNCs" in step 1) was replaced with gold nanoclusters as described in the following document 1. It can be known that, when the surface of the gold nanocluster synthesized by the solution method is covered with different surface ligands, the fluorescence lifetime is only nanosecond level and is in the same order of magnitude as the lifetime of the autofluorescence in the cell, and the interference caused by the autofluorescence material cannot be effectively avoided.
That is, in the technical scheme of the invention, the nanoclusters with microsecond-level fluorescence lifetime are synthesized by adopting the synthesis conditions of the method, and the temperature of mitochondria can be accurately measured by adopting the fluorescence lifetime.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (4)
1. A fluorescence lifetime temperature sensor of a targeted mitochondrion is characterized in that the sensor is formed by covalently coupling a gold nanocluster with a surface protected by a ligand and a triphenylphosphine compound or a derivative thereof;
wherein the ligand is glutathione;
the average diameter of the ligand-protected gold nanoclusters is 2nm or less;
the preparation method of the fluorescence lifetime temperature sensor comprises the following steps:
mixing MES solution of triphenylphosphine compound or derivative thereof, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and N-hydroxysulfonic succinimide sodium salt, adding aqueous solution of gold nanoclusters with surfaces protected by ligands after reaction and activation, carrying out light-shielding reaction, and dialyzing to obtain the fluorescence lifetime temperature sensor;
the preparation of the gold nanocluster with the surface protected by the ligand comprises the following steps:
uniformly mixing the aqueous solution of chloroauric acid and glutathione at room temperature, stirring at 70-80 ℃ until the solution is clear and light yellow, and dialyzing to obtain the gold nanoclusters with the surfaces protected by the ligands;
in the MES solution of the triphenylphosphine compound or the derivative thereof, the concentration of the triphenylphosphine compound or the derivative thereof is 6-10 mg/mL.
2. Use of the fluorescence lifetime temperature sensor according to claim 1 for mitochondrial temperature measurement.
3. The application according to claim 2, wherein the application comprises:
testing the fluorescence life of the fluorescence life temperature sensor in the range of 0-370 mu s by adopting laser with the wavelength of 390nm, and establishing an in-vitro working curve by taking the temperature as an abscissa and the fluorescence life value of the sensor as an ordinate;
the fluorescence lifetime temperature sensor is positioned on mitochondria in a targeted mode, a fluorescence lifetime imaging microscope is adopted to test the lifetime of the positioned sensor to obtain a fluorescence lifetime image, the temperature distribution of the mitochondria is determined according to the fluorescence lifetime image, and then the specific temperature corresponding to the fluorescence lifetime value is obtained according to the in-vitro working curve.
4. The use according to claim 3, wherein the fluorescence lifetime imaging microscope is tested with a femtosecond laser with a wavelength of 402nm, a laser repetition rate of 80MHz and a filter of 582/75 nm.
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| CN111781175B (en) * | 2020-06-18 | 2023-04-21 | 中国人民解放军军事科学院国防科技创新研究院 | Method, device and application for improving mitochondrial activity in cells |
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