Fluorescence enhancement type two-photon hypochlorous acid fluorescence probe, as well as preparation method and application thereof
A fluorescent probe and fluorescence enhancement technology, applied in the field of analytical chemistry, can solve problems such as poor specificity, achieve strong anti-interference ability of other molecules, simple post-processing process, and broad application prospects
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Embodiment 1
[0029] Synthesis of compound 1:
[0030]
[0031] 2-Hydroxy salicylaldehyde (2.76g, 20mmol, 2.0eq), 2-cyclohexen-1-one (2.88mg, 30mmol, 3.0eq) and triethylenediamine (Dabco 5.6g, 50mmol, 5.0eq) dissolved In a solution of 1,4-dioxane / water=1, protected by nitrogen, heated to reflux at 100° C., reacted for 40 h. Use a TLC plate to detect the reaction. After the reaction is complete, extract with ethyl acetate, dry over anhydrous sodium sulfate, concentrate, and separate with a silica gel column. The silica gel particle size is 200-300 mesh, and the eluent ratio is ethyl acetate / petroleum Ether=1:6, the yield is 12%.
[0032] Synthesis of compound TP-HA:
[0033]
[0034] Compound 1 (108mg, 0.5mmol, 1.0eq), dimethylaminothioformyl chloride (250mg, 2.0mmol, 4.0eq) and DIEA (100μL, 3.0eq) were dissolved in 3mL of dry dichloromethane, under nitrogen protection, at room temperature React for 10 hours, use a TLC plate to detect the reaction, after the reaction is complete, wa...
Embodiment 2
[0036] Changes in the fluorescence spectrum of the compound TP-HA hypochlorous acid fluorescent probe with the increase in the equivalent of hypochlorous acid
[0037] The TP-HA hypochlorous acid fluorescent probe prepared in Example 1 was dissolved in N,N-dimethylformamide (DMF) to prepare a 1 mmol / L stock solution. Take 30μL from the stock solution and add it to a 5mL centrifuge tube, add different equivalents (0-3.3eq) of hypochlorous acid standard solution, dilute to 3mL with PBS buffer solution (0.1mol / L, pH=7.5), measure its fluorescent properties. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that the fluorescence gradually increases with the increase of the equivalent of hypochlorous acid.
Embodiment 3
[0039] The selectivity of compound TP-HA hypochlorous acid fluorescent probe to different molecules or ions
[0040] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5mL centrifuge tube, add 40 times the molar amount of competing molecule standard solution, one of which is added with 1 times the molar amount of hypochlorous acid standard solution, and detect after 30min The fluorescence emission spectrum of the solution changes by image 3 and Figure 4It can be found that other metal ions have almost no effect on the fluorescence of compound TP-HA, but the addition of hypochlorous acid solution can significantly enhance the fluorescence of compound TP-HA.
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