Fluorescent probe for detecting hypochlorous acid in brain based on silicon rhodamine as well as preparation method and application of fluorescent probe
A fluorescent probe, hypochlorous acid technology, applied in the field of biomedicine, can solve the problems of limited application, short emission wavelength, poor resistance to photobleaching, etc., to achieve increased tissue penetration depth, fast and sensitive response, and low cytotoxicity. Effect
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Embodiment 1
[0038] Synthesis of Fluorescent Probe Compound SiR-FH
[0039] (1) Synthesis of Compound 1
[0040]Add 50mmol of 3-bromoaniline to the THF suspension of sodium hydride at 0°C, wherein the sodium hydride content is 125mmol in a 60% mineral oil dispersion, and the THF content is 100mL; the reactant is stirred at 0°C for 0.5 hours, Then add 125mmol ethyl iodide, and the mixture is stirred at room temperature for 24 hours; the reaction is quenched with water, and the reaction mixture is extracted three times with dichloromethane; the organic phase is dried with anhydrous sodium sulfate; the crude product is purified with a silica gel column, and Petroleum ether / dichloromethane at a volume ratio of 40:1 was used as the eluent to obtain compound 1 as a yellow oil with a yield of 73%. 1H NMR (400MHz, Chloroform-d) δ7.06(t, J=7.9Hz, 1H), 6.80(s, 1H), 6.76(d, J=7.4Hz, 1H), 6.60(d, J=7.6Hz ,1H), 3.35(q, J=7.0Hz, 4H), 1.18(t, J=7.1Hz, 6H), the synthetic route is as follows:
[0041] ...
Embodiment 2
[0051] Embodiment 2 Spectral changes of fluorescent probe SiR-FH and hypochlorous acid
[0052] Probe SiR-FH in the presence of hypochlorous acid, UV-Vis or fluorescence spectrum changes. The SiR-FH fluorescent probe prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) to make a 10 mM stock solution, and 20 μL was taken from the stock solution and diluted to 2 mL with deionized water. Hypochlorous acid is prepared with sodium hypochlorite solution, and its concentration is calibrated with the absorbance at 292nm. Use 620nm as excitation light. Scanning the fluorescence emission spectrum from 640 to 800 nm at room temperature, the fluorescence spectrum as figure 1 As shown, the UV absorption spectrum is shown as figure 2 shown. With the addition of hypochlorous acid, the fluorescence at 670 nm and the absorption at 652 nm gradually increase, and the relationship between the fluorescence intensity and the concentration of hypochlorous acid is as follows image ...
Embodiment 3
[0053] Embodiment 3 The selectivity of fluorescent probe SiR-FH to different molecules or ions
[0054] SiR-FH with a concentration of 10 μM was added to various interfering substances to test its fluorescence intensity changes, such as Figure 4 As shown, the interfering substances are H 2 o 2 ,·OH, 1 o 2 , O 2 - , etc. active oxygen, NO, NO 2 - Isoactive nitrogen, H 2 S, HSO 3 - , GSH, Cys and other active sulfur, Na + , K + , Ca 2+ , Mg 2+ , Fe 3+ ,Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ and other metal ions. The test results showed that the probe SiR-FH had no fluorescence response to interferences including active oxygen, active nitrogen, active sulfur, and metal ions, but the addition of hypochlorous acid significantly enhanced the fluorescence of the probe SiR-FH. Indicating the specific response of the probe SiR-FH to hypochlorous acid.
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