CN110028473B - Fluorescent probe for detecting polarity of lipid droplets - Google Patents
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Abstract
The invention provides a fluorescent probe for detecting polarity in a cell lipid drop, which has a chemical structural formula as follows:
. The fluorescent probe can emit stronger fluorescence in the environment of cancer cell lipid drops with smaller polarity, and can emit weaker fluorescence in the environment of normal cell lipid drops with larger polarity, so that normal cells and cancer cells can be distinguished, the fluorescent probe is accurately positioned in the lipid drops, the fluorescent probe has higher sensitivity, good optical stability and response to polarity specificity, and the detection of the polarity of intracellular lipid drops is realized. The probe of the invention can be used for evaluating and researching the content of lipid droplets in cells by a fluorescence imaging technology, and has potential application value in the research of obtaining the physiological function of the lipid droplets in the cells. Meanwhile, the probe has the advantages of simple synthesis steps, convenience in purification and high yield.
Description
Technical Field
The invention belongs to the field of organic small-molecule fluorescent probes, and particularly relates to a fluorescent probe for detecting the polarity of 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. Thus, the number of lipid droplets can be considered as a potential tumor marker for cancer diagnosis. Furthermore, due to specific alterations in lipid metabolism in cancer cells, lipid droplets are less polar in cancer cells than in normal cells. Therefore, combining the two indicators (number and polarity of lipid droplets) will provide more reliable and accurate information for cancer diagnosis. However, to our knowledge, studies to diagnose cancer by monitoring the number and polarity changes of lipid droplets have not been realized.
Cancer is one of the accepted deadlines worldwide, with a large number of people dying from cancer each year. Although cancer is an important disease, cancer mortality can be controlled if we diagnose and treat it in a timely manner. The diagnosis of cancer by tumor markers is a hot point at present, and although some existing tumor markers greatly improve the cancer diagnosis rate, the wide application of the tumor markers is limited due to the defects of invasiveness, inconvenient operation and the like. Therefore, the development of new tumor markers is of great importance for the diagnosis and treatment of cancer. In recent years, lipid droplets have attracted much attention due to their unique structure and properties. In addition to providing energy to cells, lipid droplets are also involved in many important physiological activities. It has been reported that lipid droplets are more polar in cancer cells than in normal cells due to their different metabolic mechanisms. Therefore, the polarity of lipid droplets can be used as an important index for distinguishing cancer cells from normal cells. Therefore, detecting the polarity of lipid droplets will provide important guiding information for the diagnosis of cancer.
At present, fluorescence imaging technology has become a powerful tool for detecting biological micropolar environments due to its high sensitivity, noninvasive detection and high selectivity. Therefore, the development of a new polarity probe for detecting the polarity of intracellular lipid droplets is of great significance for the diagnosis and clinical research of cancer.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a fluorescent probe capable of detecting the polarity in a lipid drop. The probe has low toxicity and good optical stability, can accurately position lipid drops and respond to polarity specificity, and can be used for detecting cancer cells by a fluorescence imaging technology.
The invention also aims to provide the application of the fluorescent probe in detecting the polarity in the cell lipid drop.
In order to achieve the purpose, the invention adopts the following technical scheme.
A fluorescent probe for detecting the polarity in a cell lipid drop has a chemical structural formula shown as a formula (I):
formula (I).
The preparation method of the fluorescent probe comprises the following steps:
(1) 3-nitro-7-diethylamino coumarin (1) and stannic chloride are stirred in concentrated hydrochloric acid to react, and the compound 3-amino-7-diethylamino coumarin (2) is obtained by separation and purification.
(2) Heating 3-amino-7-diethylamino coumarin (2) and p-fluoronitrobenzene in dimethyl sulfoxide for reaction, adding cesium fluoride for catalytic reaction, separating and purifying to obtain a compound 3- (bis 4-nitrophenyl) amino-7-diethylamino coumarin (3), namely a fluorescent probe:
in the step (1), the mass ratio of the material 3-nitro-7-diethylamino coumarin (1) to the tin chloride is 1: 3.
In the step (1), the separation and purification step is to add sodium hydroxide solution into the reaction solution for neutralization until the solution is neutral, precipitate yellow, filter the solution, and pass the filter residue through a silica gel column by taking dichloromethane/methanol =20:1v/v as eluent.
In the step (2), the mass ratio of the material 3-amino-7-diethylamino coumarin (2) to the p-fluoronitrobenzene is 1: 2.
In the step (2), the separation and purification step is to separate out yellow precipitate from the reaction solution by using deionized water, pump-filtering, and passing filter residue through a silica gel column by using dichloromethane/methanol =20:1v/v as eluent.
An application of the fluorescent probe in detecting the polarity of lipid droplets in cells.
The mechanism of the invention is as follows:
since the carbonyl structure of coumarin is a strong electron-withdrawing group and the diethylamino group is an electron-donating group, in the probe structure, there is electron transfer from the "diethylamino" moiety to the "carbonyl" moiety, i.e., intramolecular electron transfer (ICT) effect. It is this ICT effect that gives the probe a "solvation effect". In a certain polarity range, such as before the polarity of a tetrahydrofuran solvent, the fluorescence intensity of the probe is gradually increased along with the increase of the polarity of the polar solvent due to the fact that the negative solvent effect is the main effect; after the polarity of the tetrahydrofuran solvent is further increased along with the polarity of the solvent, the fluorescence intensity of the probe is reduced along with the change of the polarity due to the dominant effect of the positive solvent. However, the polarity of lipid droplets precedes that of tetrahydrofuran in both normal and cancer cells, and lipid droplets in cancer cells are less polar than those in normal cells. Therefore, the probe emits stronger fluorescence in the environment of the lipid drop of the cancer cell with smaller polarity, and emits weaker fluorescence in the environment of the lipid drop of the normal cell with larger polarity. Therefore, normal cells can be distinguished from cancer cells by a change in fluorescence intensity, thereby achieving diagnosis for diagnosing cancer.
The invention has the following advantages:
the fluorescent probe provided by the invention can distinguish normal cells from cancer cells, can be accurately positioned in lipid droplets, has higher sensitivity, good optical stability and specific response to polarity, and realizes the detection of the polarity of lipid droplets in cells. The probe of the invention can be used for evaluating and researching the content of lipid droplets in cells by a fluorescence imaging technology, and has potential application value in the research of obtaining the physiological function of the lipid droplets in the cells. Meanwhile, the probe has the advantages of simple synthesis steps, convenience in purification and high yield.
Drawings
FIG. 1 shows a fluorescent probe1H NMR spectrum;
FIG. 2 shows UV spectra of fluorescent probes in different polar solvents. Concentration of the probe: 5 mu M;
FIG. 3 is a fluorescence spectrum of a fluorescent probe in solvents of different polarities. Wherein the excitation wavelength is 405 nm; concentration of the probe: 10 mu M;
FIG. 4 is a cell imaging test of fluorescent probes on mouse fibroblasts (3T 3) and mouse breast cancer cells (4T-1). The concentration of the probe is 10 MuM, and the excitation wavelength is 405 nm;
FIG. 5 is a tissue imaging test of fluorescent probes in mouse tumor tissue. The probe concentration was 10. mu.M and the excitation wavelength was 405 nm.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
EXAMPLE 1 Synthesis of fluorescent Probe
(1) Stirring the 3-nitro-7-diethylamino coumarin (1) and tin chloride in concentrated hydrochloric acid (the molar ratio is 1: 3), reacting for 6 hours, adding a sodium hydroxide solution for neutralization until the solution is neutral, separating out yellow precipitate, performing suction filtration, and purifying to obtain a compound 3-amino-7-diethylamino coumarin (2):
(2) stirring 3-amino-7-diethylaminocoumarin (2) and p-fluoronitrobenzene in dimethyl sulfoxide (the molar ratio is 1: 2), reacting for 1 hour, adding a catalyst, namely cesium fluoride, reacting for 12 hours, precipitating yellow precipitate by using deionized water, and performing suction filtration and purification to obtain a compound, namely 3- (bis 4-nitrophenyl) amino-7-diethylaminocoumarin, namely a fluorescent probe:
it is composed of1The H NMR spectrum is shown in FIG. 1.
Example 2 ultraviolet spectra of fluorescent probes in solvents of different polarity
A1 mM stock solution of the fluorescent probe obtained in example 1 was prepared for use, and dimethyl sulfoxide was used as a solvent. Add 10. mu.L of the probe stock solution to 2 mL of a solvent of different polarity to a final probe concentration of 5. mu.M. The solvents are arranged from small to large according to the polarity: toluene, 1, 4-dioxane, tetrahydrofuran, dichloromethane, dimethyl sulfoxide, methanol and deionized water. The ultraviolet absorption spectrum of each solvent was measured as shown in FIG. 2. As can be seen from FIG. 2, the probes have different maximum absorption wavelengths in solvents of different polarities.
Example 3 fluorescence Spectroscopy of fluorescent probes in solvents of different polarity
10 mL of a 1 mM stock solution of the fluorescent probe obtained in example was prepared for use, and dimethyl sulfoxide was used as a solvent. Add 20. mu.L of the probe stock solution to 2 mL of a solvent of different polarity to a final probe concentration of 10. mu.M. The solvents are arranged from small to large according to the polarity: toluene, 1, 4-dioxane, tetrahydrofuran, dichloromethane, dimethyl sulfoxide, methanol and deionized water. The excitation wavelength was 415nm, and the fluorescence spectrum of the fluorescent probe in each solvent was detected, as shown in FIG. 3. With increasing polarity, the maximum emission wavelength of the probe shows a clear red-shift trend.
EXAMPLE 4 cellular imaging assays of fluorescent probes at 3T3 and 4T-1
10 mL of a 1 mM stock solution of the fluorescent probe obtained in example was prepared for use, and dimethyl sulfoxide was used as a solvent. mu.L of the probe stock was added to 3T3 cells (mouse fibroblasts) and 4T-1 (mouse breast cancer cells) 0 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 excitation wavelength is 405 nm, as shown in figure 4. As can be seen from FIG. 4, the fluorescent probe aggregated in the mouse breast cancer cell (4T-1) and emitted green fluorescence, whereas the fluorescent probe did not emit fluorescence in the mouse fibroblast cell (3T 3).
Example 5 Co-localization of fluorescent probes with commercial lipid droplet dyes in mouse mammary tumor cells
Preparing a test mother solution of dimethyl sulfoxide of the fluorescent probe obtained in example at a concentration of 1 mM for use; the test mother liquor of dimethyl sulfoxide, a commercial specific localization agent for nile red drops, was prepared at a concentration of 20 μ M for use. Inoculating mouse mammary tumor cells with proper density into a sterilized imaging culture dish, culturing in an incubator, and after the cells adhere to the wall, simultaneously and respectively adding lipid drops of commercial dyes Nile Red, fluorescent probes and Nile Red + probes into the three groups of cells to ensure that the final concentration of the fluorescent probes is 10 mu M and the final concentration of the Nile Red is 5 mu M. After half an hour, the medium was discarded, and the cells were washed (3) times with PBS buffer (pH = 7.2) followed by fluorescence imaging with a green excitation wavelength of 405 nm and a red excitation wavelength of 561 nm. . Fluorescence photographs of cells incubated with nile red, fluorescent probe and nile red + probe were taken separately in single photon mode with a fluorescence microscope, as shown in fig. 5. As can be seen from FIG. 5, the fluorescent probe emits green fluorescence in the cells; nile red, in cells, emits red fluorescence; while the nile red + probe emits overlapping yellow fluorescence in the cell. Experimental results show that the probe can accurately position intracellular lipid droplets.
Claims (6)
1. A fluorescent probe for detecting the polarity in a cell lipid drop has a chemical structural formula shown as a formula (I):
formula (I).
2. A method of preparing a fluorescent probe according to claim 1, comprising the steps of:
(1) stirring 3-nitro-7-diethylamino coumarin and stannic chloride in concentrated hydrochloric acid for reaction, and separating and purifying to obtain a compound 3-amino-7-diethylamino coumarin:
(2) heating 3-amino-7-diethylamino coumarin and p-fluoronitrobenzene in dimethyl sulfoxide for reaction, adding cesium fluoride for catalytic reaction, separating and purifying to obtain a compound 3- (bis 4-nitrophenyl) amino-7-diethylamino coumarin, namely a fluorescent probe:
3. the preparation method according to claim 2, wherein in the step (1), the mass ratio of the 3-nitro-7-diethylamino coumarin to the tin chloride is 1: 3; in the step (2), the mass ratio of the 3-amino-7-diethylamino coumarin to the p-fluoronitrobenzene is 1: 2.
4. The preparation method according to claim 2, wherein in the step (1), the separation and purification step comprises adding a sodium hydroxide solution into the reaction solution for neutralization until the solution is neutral, separating out a yellow precipitate, performing suction filtration, and passing the filter residue through a silica gel column by using dichloromethane/methanol =20:1v/v as a leacheate.
5. The preparation method according to claim 2, wherein in the step (2), the separation and purification step comprises separating out a yellow precipitate from the reaction solution with deionized water, performing suction filtration, and passing the filter residue through a silica gel column with dichloromethane/methanol =20:1v/v as eluent.
6. Use of the fluorescent probe of claim 1 in the preparation of a reagent for detecting the polarity of lipid droplets in cells.
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| CN110981842B (en) * | 2019-11-15 | 2021-07-02 | 郑州大学 | Fluorescent probe for distinguishing normal cells and cancer cells and specifically detecting lipid droplets and application |
| CN113603654B (en) * | 2021-07-14 | 2022-07-22 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates as well as preparation method and application thereof |
| CN113845519B (en) * | 2021-09-18 | 2022-05-31 | 山西大学 | Microenvironment sensitive type fluorescent probe and preparation method and application thereof |
| CN113773292B (en) * | 2021-09-29 | 2022-06-10 | 皖南医学院 | Washing-free AIEgen fluorescent probe targeting lipid droplets and preparation method and application thereof |
| CN114702507B (en) * | 2022-05-23 | 2023-04-04 | 济南大学 | Fluorescent probe for detecting lipid droplets and endoplasmic reticulum |
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
| CN108822019A (en) * | 2018-08-21 | 2018-11-16 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
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| Rational design of a lipid-droplet-polarity based fluorescent probe for potential cancer diagnosis;Junling Yin 等;《Chem. Commun.》;20181227;第54卷;12093-12096 * |
| Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications;Baoxin Zhang 等;《J. Am. Chem. Soc.》;20150105;第137卷;757-769 * |
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