A lysosome-targeted hypochlorous acid molecular fluorescent probe and its preparation method and application
A fluorescent probe, hypochlorous acid technology, applied in the field of analytical chemistry, can solve the problems of lack of hypochlorous acid detection tools, lack of targeting of hypochlorous acid, inability to detect hypochlorous acid, etc., and achieve strong resistance to other molecular interference. , the effect of high coincidence rate and simple post-processing process
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Embodiment 1
[0036] Preparation of target probe compound Lyso-ClO
[0037] (1) Synthesis of compound Lyso-1
[0038]4-Diethylaminoketonic acid (1.0 g, 3.19 mmol, 1 eq) and 4-benzothiazole-1,3-resorcinol (776 mg, 3.19 mmol, 2 eq) were dissolved in 5 mL of methanesulfonic acid solution , under nitrogen protection, heated at 90°C, and reacted for 24 h. Use a TCL plate to detect the reaction. After the reaction is complete, cool the reaction solution to room temperature, slowly pour the reaction solution into 50 mL of ice water, extract with methanol / dichloromethane = 1:10, dry over anhydrous sodium sulfate, and spin dry under reduced pressure. The crude product was obtained from the solvent, and was separated with a silica gel column, the silica gel particle size was 200-300 mesh, the eluent ratio was methanol / dichloromethane=1:30, and the yield was 64%. The synthetic route is as follows:
[0039]
[0040] (2) Synthesis of compound Lyso-2
[0041] Compound Lyso-1 (300 mg, 0.574 mmol, 1...
Embodiment 2
[0050] Changes in the fluorescence spectrum of the compound Lyso-ClO hypochlorous acid fluorescent probe with the increase in the equivalent of hypochlorous acid
[0051] The Lyso-ClO hypochlorous acid fluorescent probe prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) 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 (0-30 eq) of hypochlorous acid standard solution, and use PBS buffer solution (0.1mol / L, pH=7.5) and DMSO at a volume ratio of 1 :1 solution diluted to 3 mL, with 365nm as the excitation light, to measure its fluorescence properties. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that the fluorescence at 450 nm gradually weakens and the fluorescence at 585 nm increases gradually with the increase of hypochlorous acid equivalent added.
Embodiment 3
[0053] The Selectivity of Compound Lyso-ClO Hypochlorous Acid Fluorescent Probe to Different Molecules or Ions
[0054] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5mL centrifuge tube, add equimolar amounts of competing molecular standard solutions, one of which is added with equimolar amounts of hypochlorous acid standard solution, and after 30 minutes, use PBS: DMF (1:1) is solvent, and 365nm is excitation light, detects the fluorescence emission spectrum change of solution, and the result is as follows image 3 shown. Simultaneously, the influence of other metal ions on the fluorescence intensity of the probe of the present invention has also been studied. With PBS:DMF (1:1) as the solvent, 410 nm is the excitation light, and the results are as follows: Figure 4 shown. Depend on image 3 and Figure 4 In general, it can be found that other metal ions have almost no effect on the fluorescence of compound Lyso-ClO at 585nm, but the a...
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