Fluorescent probe for detecting hydrogen sulfide in cells, method for preparing fluorescent probe and application thereof
A fluorescent probe, hydrogen sulfide technology, applied in the field of analytical chemistry, to achieve the effect of cheap raw materials, low preparation cost, and simple and easy synthesis process
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Embodiment 1
[0032] Example 1 Synthesis of Fluorescent Probes
[0033] (1) Add 4-ethynylbenzonitrile (1 mmol), 4-bromo-2-hydroxybenzaldehyde (1 mmol), triphenylphosphine (0.02mmol), [1,1-bis(diphenylphosphine Base) Ferrocene] Palladium dichloride (0.02 mmol) was dissolved in triethylamine, after stirring for 10 min, cuprous iodide (0.04 mmol) was added to the reaction system, and heated to reflux at 90°C for 2 hours under the protection of nitrogen , using petroleum ether:ethyl acetate=5:1v / v as the eluent, separated and purified by column chromatography to obtain compound 1: ;
[0034] (2) Dissolve compound 1 (0.3 mmol), 2,4-dinitrofluorobenzene (0.35 mmol) and N,N-diisopropylethylamine (0.3 mmol) in 10 mL of dichloromethane, at room temperature The reaction was stirred for 6 hours, and the target product was obtained by separation and purification by column chromatography with petroleum ether:ethyl acetate=2:1v / v as eluent. 1 H NMR spectrum see figure 1 .
Embodiment 2
[0035] Example 2 Fluorescent probes for different concentrations of Na 2 S's response
[0036] The probe obtained in Example 1 was dissolved in ethanol, and then diluted with PBS to form a 5 μM probe buffer solution (containing 10% ethanol, pH 7.4). Take 22 parts of the above probe solution, add Na 2 The concentration of S solution is: 0, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 120, 130, 150, 170, 190, 210, 230, 260, 280, 290, 300 μM, followed by fluorescence detection (λ Ex = 405 nm); calculate the relative fluorescence intensity in each system; the probe has different concentrations of Na 2 S responds as figure 2 Shown: the maximum fluorescence intensity peak is at 510 nm, with Na 2 The fluorescence intensity increased gradually with the increase of S solution concentration. Take Na 2 When the concentration of S is 0, 10, 20, 30, and 40 μM, the concentration of the detected substance is the abscissa, and the corresponding fluorescence intensity at 510 nm (I 510nm ...
Embodiment 3
[0037] Example 3 Selectivity of fluorescent probes to different substances
[0038] The probe obtained in Example 1 was dissolved in ethanol, and then diluted with PBS to form a 5 μM probe buffer solution (containing 10% ethanol, pH 7.4). Take 22 parts of the above probe solution with a volume of 4 mL, add 20 μL of PBS solutions of different substances with a concentration of 40 mM, and then perform fluorescence scanning (λ Ex = 405 nm); calculate the relative fluorescence intensity in each system; take the corresponding fluorescence intensity at 510 nm (I 510nm ) is the ordinate, and the histogram of the response of the probe to different substances is obtained, such as Figure 4 Shown, among them, 1-22 are respectively blank, Al 3+ 、 Ba 2+ , Ca 2+ 、Co 2+ 、Cu 2+ , Cys, F - , glucose, GSH, H 2 o 2 , HClO, Hcy, I - , Mg 2+ , MnO 2 、Ni 2+ , Sn 2+ , SO 3 2- , VC, Zn 2+ 、Na 2 S. It can be seen that the fluorescent probe is only sensitive to the addition of Na ...
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