Lipid droplet fluorescent probe and synthetic method and application thereof
A technology of fluorescent probes and lipid droplets, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high cost, fewer fluorescent probes, cumbersome synthesis steps, etc., and achieve easy application and simple synthesis route , to achieve the effect of intracellular imaging
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[0029] Example 1 Synthesis of PIA.
[0030] Dissolve 0.25g (1.2mmol) 9,10-phenanthrenequinone and 0.18g (1mmol) N,N-diethyl-4-aminobenzaldehyde in 20mL acetic acid, add 0.38g (5mmol) ammonium acetate as a catalyst, The reaction was refluxed at 100°C for 12 h under nitrogen protection. After the reaction, it was cooled to room temperature, poured into ice water and stirred, adjusted to pH neutral, filtered with suction, and dried in a vacuum drying oven to obtain the probe compound, yield: 80%. The hydrogen nuclear magnetic spectrum of the probe compound is shown as figure 1 Shown.
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[0031] Example 2 Solvation effect of PIA.
[0032] The probe in Example 1 was dissolved in dimethyl sulfoxide to prepare a concentration of 10 -3 The mother liquor of M. Take 50μL of the above mother liquor and add them to nine identical 5mL volumetric flasks. Use DMF, DMSO, THF, MeCN, PBS, MeOH, DCM, H 2 O, Dioxane is diluted to 5mL, and then fluorescent detection, the result is figure 2 :by figure 2 It can be seen that the fluorescence intensity of the probe in the organic solution is much greater than in the water phase. This shows that when the detection environment is in the water phase, the fluorescence intensity of the probe in the water is significantly weaker, making the probe better for the detection of human environment, greatly reducing the hazard of the probe to the human body, and eliminating Own interference.
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[0033] Example 3 Cellular co-localization of PIA.
[0034] The probe in Example 1 was prepared with DMSO into a 1 mM stock solution, and 5 μL of the stock solution was diluted with 1 mL of culture medium during staining to prepare a staining solution with a final concentration of 5 μM. Incubate the inoculated cells in the staining solution at 37 ºC for 30 min, wash 3 times with PBS, and place the adherent cells on a glass slide; then use a fluorescence microscope to perform fluorescence imaging with an excitation wavelength of 405nm and an emission wavelength of 425- 475nm. At the same time, a commercial lipid droplet probe (BODIPY493 / 503) was used for co-localization experiments, with an excitation wavelength of 488nm and an emission wavelength of 500-550nm. The image under the confocal fluorescence microscope is like image 3 As shown, from left to right are bright field imaging, PIA probe imaging, BODIPY493 / 503 probe imaging, bright field, PIA probe and BODIPY493 / 503 probe su...
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