CN110031436B - Organic silicon fluorescent probe for detecting lipid drops - Google Patents
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Abstract
The invention provides an organic silicon fluorescent probe for detecting lipid droplets, which comprises the following components in parts by weight:
. The probe of the invention has AIE effect, and different cells can be distinguished by judging the intensity of fluorescence. The probe can be used for evaluating and researching the physiological function of the cancer cell by a fluorescence imaging technology, and has potential application value in the research of obtaining the physiological function of the cancer cell.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for detecting lipid droplets and application thereof.
Background
Lipid droplets have recently received attention from a wide range of researchers due to their specific structure and physiological function. Lipid droplets, widely present in eukaryotic cells as lipid-rich subcellular organelles, consist of a core of neutral lipids surrounded by a monolayer of phospholipids mounting the proteins of interest. In addition to acting as an energy reservoir, lipid droplets are also involved in various physiological processes, including cell activation, migration, proliferation, apoptosis, and the like. There is increasing evidence that abnormalities in lipid droplets are associated with cancer development. It has been reported that the number of lipid droplets in cancer cells is higher than in normal cells, because the large amount of energy provided by lipid droplets is necessary for faster proliferation of cancer cells. Furthermore, due to specific alterations in lipid metabolism in cancer cells, lipid droplets are less polar in cancer cells than in normal cells. Thus, combining the two indices (number and polarity of lipid droplets) allows localization of cancerous cells. However, studies to locate cancerous cells by monitoring the number and polarity changes of lipid droplets are not currently available.
The traditional method for detecting cancer cells has many inconveniences and limitations, and fluorescent probes are rapidly developed in recent years due to the advantages of rapidness, convenience, high sensitivity, instant detection, rapid response and the like. These advantages make it have more extensive application in the subject field such as chemistry, biomedicine, especially in the biomedicine field, and fluorescence probe not only can be used for in vitro analysis but also can be used for the image study of living body. In recent years, a large number of small molecule fluorescent probes have been reported for detecting cancer cells. However, many of the probes have poor water solubility, low sensitivity, large influence on the detection effect due to pH change, and other probes have high biotoxicity and poor cell membrane permeability, and the defects greatly influence the application of small molecular probes. Therefore, the development of stable and sensitive probes for detecting cancer cells is of great significance.
Disclosure of Invention
Aiming at the problems of poor water solubility, low sensitivity, large influence of pH change on the detection effect, large biotoxicity of the probe and poor cell membrane permeability of the existing probe, the invention provides the organic silicon fluorescent probe for detecting the lipid drop, which has high response speed and strong anti-interference capability.
The invention also aims to provide the application of the fluorescent probe in detecting lipid droplets in cells.
In order to achieve the purpose, the invention adopts the following technical scheme.
An organic silicon fluorescent probe for detecting lipid droplets, referred to as TR, has a chemical structural formula shown as formula (I):
formula (I).
The preparation method of the organic silicon fluorescent probe comprises the following steps:
(1) heating aminopropyl silicone oil and 4-bromo-1, 8-naphthalic anhydride in ethanol for reflux reaction, filtering after the reaction is finished, and mixing filter residues with methanol in a volume ratio of 1: 20: and (3) passing dichloromethane serving as eluent through a silica gel column, and then drying to obtain a compound 1:
(2) under protective atmosphere, compound 1 and 4-triphenylamine borate in toluene at K2CO3In the presence of tetrakis (triphenylphosphine) palladium for catalytic heating reflux reaction, after the reaction is finished, the reaction is carried out by adding methanol with the volume ratio of 1: 10: and (3) passing dichloromethane serving as eluent through a silica gel column, and drying to obtain the organic silicon fluorescent probe:
the mass ratio of the aminopropyl silicone oil to the 4-bromo-1, 8-naphthalic anhydride is 5: 1.
The mass ratio of the compound 1 to the 4-triphenylamine borate is 1: 0.8-1.
In the step (1) and the step (2), the reaction temperature was 80 ℃.
An application of the organic silicon fluorescent probe in preparation of a reagent for detecting the number of cell lipid drops and polarity.
The mechanism of the invention is as follows:
the probe TR of the present invention has an AIE effect and is poorly soluble in lipid droplets. When the lipid droplet content in the cell is increased, the polarity of the cell is reduced, so that the probe TR content in the cytoplasm is relatively increased, the fluorescence intensity is increased, and the emission wavelength is blue-shifted. Different cells can be distinguished by judging the intensity of fluorescence.
The invention has the following advantages:
the fluorescent probe provided by the invention distinguishes cancer cells from normal cells through polarity change, and the result and the phenomenon thereof lay a theoretical foundation for biological imaging application, indicating that the fluorescent probe has potential application value in the field of laser-excited fluorescent biomarkers. Correspondingly, the probe of the invention can be used for evaluating and researching the physiological function of the cancer cell by a fluorescence imaging technology, and has potential application value for researching and obtaining the physiological function of the cancer cell.
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FIG. 1 is a nuclear magnetic spectrum of a probe;
FIG. 2 shows fluorescence spectra of probes in solvents of different polarities. Wherein the excitation wavelength is 405 nm; concentration of the probe: 10 mu M;
FIG. 3 is a fluorescence spectrum of the probe in a mixed solution of petroleum ether and tetrahydrofuran at different ratios. Wherein the excitation wavelength is 405 nm; the concentration of the probe is 10 mu M;
FIG. 4 is cytotoxicity after 24h incubation of the probe;
FIG. 5 is a cell imaging test of probes on mouse fibroblasts (3T 3) and mouse breast cancer cells (4T-1). The probe concentration was 10. mu.M and the excitation wavelength was 405 nm.
Detailed Description
The present invention is further illustrated by the following examples and figures, but is not limited by the following examples, the compound numbers corresponding to the reaction formulae in the summary of the invention.
EXAMPLE 1 Synthesis of fluorescent Probe
(1) Firstly, 2 g of aminopropyl silicone oil is dissolved in 20 mL of ethanol, then 0.4 g of 4-bromo-1, 8-naphthalic anhydride is dissolved in 40 mL of ethanol, the obtained solution is added into a 100 mL eggplant-shaped reaction bottle together, the temperature is raised to 80 ℃, and the reflux reaction is carried out for 8 hours. After the reaction is finished, filtering to obtain a solid, purifying by column chromatography (methanol: dichloro = 1: 20), and drying to obtain a compound 1;
(2) 0.37 g of Compound A was dissolved in 20 mL of toluene, and 0.346 g of triphenylamine-4-borate was dissolved in 20 mL of toluene and collectively charged into a 100 mL eggplant-type reaction flask. 0.058 g of tetrakis (triphenylphosphine) palladium, 2 mL of K were added thereto2CO3(ii) 2 mol/L. Stirring for 10 h at 80 ℃ under the protection of nitrogen. After the reaction, the product was purified by column chromatography (methanol: dichloro = 1: 10), and dried to obtain compound TR. It is composed of1The H NMR spectrum is shown in FIG. 1.
Example 2 fluorescence spectra of fluorescent probes in solvents of different polarity
10 mL of the mother solution of the macromolecular fluorescent probe TR with the concentration of 1 mM for polarity detection is prepared for standby. Add 20. mu.L of the probe stock to 2 mL of a solvent of different polarity (probe concentration 10. mu.M). The solvents are arranged from small to large according to the polarity: toluene, dichloro, tetrahydrofuran, 1, 4-dioxane, acetonitrile, DMF, DMSO. The excitation wavelength was 405 nm. The results are shown in FIG. 2: the maximum emission peak of probe TR is gradually red-shifted with increasing polarity of the solvent.
Example 3 fluorescence spectra of fluorescent probes in different ratios of Petroleum Ether to tetrahydrofuran
10 mL of the mother solution of the macromolecular fluorescent probe TR with the concentration of 1 mM for polarity detection is prepared for standby. Respectively preparing 2 mL of mixed solvent of petroleum ether and tetrahydrofuran in different proportions, wherein the mixed solvent comprises the following components: tetrahydrofuran =0, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%. The fluorescence spectra were measured by adding 10. mu.L of the mother liquor to 2 mL of different polar solvents, with an excitation wavelength of 405nm, and the results are shown in FIG. 3: the fluorescence intensity gradually increases with increasing volume of petroleum ether in the volume. This is because the probe has poor solubility in petroleum ether, and increasing the percentage of petroleum ether in the solvent is equivalent to aggregating the probe TR, increasing the intensity, indicating that the probe TR has AIE effect and blue-shifting the emission wavelength.
Example 4 toxicity of fluorescent probes to cells
HeLa cells with a cell density of 8000 cells/mL were seeded into a portion of the wells of a 96-well plate, the remaining wells were filled with cell-free medium and subjected to CO under different conditions2Cells were incubated in an incubator. The experimental group is a cell sample after 24 hours of incubation with a medium containing 1-30 μ M TR, the control group is a cell-containing sample without dye, and the blank group is a cell-free medium sample. After the incubation was complete, the cell culture was replaced with fresh medium and 10 μ L of MTT was added to each well and the cells were incubated for an additional 4 hours. After the incubation was completed, the medium was removed, 200 μ L of DMSO was added to each well, and it was shaken with a shaker for 10min to dissolve formazan. The absorbance at 440nm of each well was measured using a microplate reader, and the cell viability was calculated by the following formula:
wherein A issampleAbsorbance for experimental group, AcAbsorbance of control group, AbAbsorbance of blank. As shown in FIG. 4, when the concentration of the TR probe was 10. mu.M or less after 24 hours of staining, the cell survival rate reached 90% or more, indicating that the toxicity of the probe was low.
Example 5 imaging applications of fluorescent probes in different cells
Probe TR stock was prepared at 1 mM and 10. mu.M of probe stock was added to 3T3 and 4T-1 cells, respectively, and incubated for 20 min. After the culture is finished, fluorescence photographs of 3T3 and 4T-1 cells are respectively taken by a fluorescence microscope in a single photon mode, and the results are shown in FIG. 5: probe TR accumulated in mouse breast cancer cells (4T-1) and emitted green fluorescence, whereas in mouse fibroblasts (3T 3), probe TR did not emit fluorescence. Since the number of lipid droplets in 4T-1 cells is higher than that in normal cells and the polarity of lipid droplets is much lower than that in 3T3 cells, probe TR accumulates in 4T-1 cells with increased fluorescence intensity due to the AIE effect.
Claims (4)
1. An organic silicon fluorescent probe for detecting lipid droplets has a chemical structural formula as follows:
the preparation method of the organic silicon fluorescent probe comprises the following steps:
(1) heating aminopropyl silicone oil and 4-bromo-1, 8-naphthalic anhydride in ethanol for reflux reaction, filtering after the reaction is finished, and mixing filter residues with methanol in a volume ratio of 1: 20: and (3) passing dichloromethane serving as eluent through a silica gel column, and then drying to obtain a compound 1:
(2) under protective atmosphere, compound 1 and 4-triphenylamine borate in toluene at K2CO3In the presence of tetrakis (triphenylphosphine) palladium for catalytic heating reflux reaction, after the reaction is finished, the reaction is carried out by adding methanol with the volume ratio of 1: 10: and (3) passing dichloromethane serving as eluent through a silica gel column, and drying to obtain the organic silicon fluorescent probe:
the mass ratio of the aminopropyl silicone oil to the 4-bromo-1, 8-naphthalic anhydride is 5: 1; the mass ratio of the compound 1 to the 4-triphenylamine borate is 1: 0.8-1.
2. The method for preparing the organosilicon fluorescent probe according to claim 1, comprising the following steps:
(1) heating aminopropyl silicone oil and 4-bromo-1, 8-naphthalic anhydride in ethanol for reflux reaction, filtering after the reaction is finished, and mixing filter residues with methanol in a volume ratio of 1: 20: and (3) passing dichloromethane serving as eluent through a silica gel column, and then drying to obtain a compound 1:
(2) under protective atmosphere, compound 1 and 4-triphenylamine borate in toluene at K2CO3In the presence of tetrakis (triphenylphosphine) palladium for catalytic heating reflux reaction, after the reaction is finished, the reaction is carried out by adding methanol with the volume ratio of 1: 10: and (3) passing dichloromethane serving as eluent through a silica gel column, and drying to obtain the organic silicon fluorescent probe:
the mass ratio of the aminopropyl silicone oil to the 4-bromo-1, 8-naphthalic anhydride is 5: 1; the mass ratio of the compound 1 to the 4-triphenylamine borate is 1: 0.8-1.
3. The method according to claim 2, wherein the reaction temperature in the step (1) and the step (2) is 80 ℃.
4. The use of the organosilicon fluorescent probe of claim 1 in the preparation of a reagent for detecting the number of lipid droplets in cells and polarity.
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