A kind of fluorescent probe and its preparation method and application
A fluorescent probe and reaction technology, applied in the field of fluorescent probes, can solve the problems of lack of high tissue penetration and stability near-infrared fluorescent probes, few reaction types, etc., and achieve strong resistance to photobleaching and other molecular interference. The effect of strong ability and low detection limit
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[0039] In one embodiment of the present invention, a kind of preparation method of above-mentioned fluorescent probe is provided, comprises the following steps:
[0040] 1) Synthesis of compound Cou-1:
[0041] 2,3,3-Trimethylindole and ethyl iodide were mixed, dissolved in anhydrous acetonitrile for reflux reaction, and after the reaction was completed, the obtained solid precipitate was washed and dried to obtain a red solid Cou-1;
[0042] 2) Synthesis of compound Cou-2:
[0043] Under the condition of nitrogen protection, sodium acetate and acetic anhydride were mixed, and the obtained Cou-1 and o-benzaldehyde cyclohexene were added to the above system; after the reaction was completed, the product was washed and dried to obtain a yellow-green solid Cou- 2;
[0044] 3) Synthesis of compound Cou-3:
[0045] Dissolve the obtained Cou-2 and 1,4-benzenediol in anhydrous acetonitrile, then add the catalyst potassium carbonate, stir at room temperature, and then put it in an ...
Embodiment 1
[0061] (1) Synthesis of compound Cou-1:
[0062] Add the compound 2,3,3-trimethylindole (1mL, 6.2mmol) and ethyl iodide (0.75mL, 9.4mmol) into a 50mL round-bottomed flask respectively, then add 12mL of anhydrous acetonitrile, mix well and put Reflux reaction in 75°C oil bath for 10 hours. After the reaction was completed, the system was cooled to room temperature, and then concentrated by vacuum rotary evaporation to remove the solvent to obtain a red precipitate. The precipitate was washed three times with petroleum ether, and the final product was suction filtered and dried to obtain a red solid compound Cou-1. The conversion rate was was 78%.
[0063] (2) Synthesis of compound Cou-2:
[0064] Compound sodium acetate (0.13g, 1.6mmol) and acetic anhydride were added to a 50mL round bottom flask, mixed and shaken, then o-benzaldehyde cyclohexene (0.34g, 2mmol) and compound Cou-1 (0.945g, 3mmol) were added , the whole reaction was reacted at 60°C for 4 hours under the protec...
Embodiment 2
[0074] The optical property test is carried out to the probe prepared in embodiment 1:
[0075] Weigh 26 mg of the purified probe solid, add analytically pure DMSO to make a 10 mM probe solution, then wrap it with tin foil and store it in the refrigerator for later use, and dilute the probe to a standard 1 mM probe solution during chemical system testing conduct experiment.
[0076] like figure 1 As shown, after adding cysteine, the probe has an absorption peak at 708nm. Under single-photon excitation at 682nm, the fluorescence intensity at 708nm of the system after the probe reacted with cysteine was significantly enhanced, and the fluorescence intensity increased with the increase of cysteine concentration, and a corresponding linear equation was obtained. like figure 2 As shown, the linear equation is y=9.711[Cys](μΜ)+216.625, and the correlation coefficient is 0.9772.
[0077] The selectivity experiment of the fluorescent probe prepared in embodiment 1 to small mo...
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