Hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and two-photon property as well as preparation method and application of hydrogen sulfide molecule fluorescent probe
A fluorescent probe and two-photon technology, applied in the field of analytical chemistry, can solve the problems of lack of targeted probes, lack of hydrogen sulfide detection tools, lack of hydrogen sulfide probes, etc., to achieve strong anti-interference ability of other molecules, Improved selection specificity and simple post-processing
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Embodiment 1
[0035] Synthesis of compound 1-1:
[0036]
[0037] 4-Bromo-1,8 naphthalene dioic anhydride (2.77g, 10mmol, 1eq), β-alanine (1.34g, 15mmol, 1.5eq) were dissolved in 30mL of methanol, under nitrogen protection, heated at reflux at 75°C for 6h. The reaction was detected with a TCL plate. After the reaction was complete, it was cooled to room temperature, and solids were precipitated. The solid was filtered and dried to obtain a crude product with a yield of 68%. Directly cast the next reaction.
[0038] Synthesis of compound 1-2:
[0039]
[0040]Triphenylphosphine (2.0g, 7.54mmol, 1eq), 3-bromopropylamine hydrobromide (1.65g, 7.54mmol, 1eq) were dissolved in 20mL of acetonitrile, under nitrogen protection, and heated at reflux at 85°C for 16h. The reaction was detected with a TCL plate, and after the reaction was complete, it was cooled to room temperature. Add 20mL of petroleum ether, a solid precipitates out, the solid is filtered and washed with petroleum ether to ...
Embodiment 2
[0048] Compound Mito-H 2 S hydrogen sulfide fluorescent probe with Na 2 The change of fluorescence spectrum with the increase of S addition equivalent
[0049] Get the Mi prepared by Example 1 t o-H 2 The S fluorescent probe was dissolved in dimethyl sulfoxide (DMSO) to make a 1 mmol / L stock solution. Take 30μL from the stock solution and add it to a 5mL centrifuge tube, dilute to 3mL with a solution of PBS buffer solution (0.1mol / L, pH=7.4) and DMSO with a volume ratio of 2:1, and add different equivalents (0-30eq) The standard solution of sodium sulfide was used to measure its fluorescence properties with 440nm excitation light. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that with Na 2 The fluorescence increases gradually with the increase of S addition equivalent.
Embodiment 3
[0051] Compound Mito-H 2 Selectivity of S fluorescent probes to different molecules or ions
[0052] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5 mL centrifuge tube, dilute it to 3 mL with a solution of PBS buffer solution (0.1 mol / L, pH=7.4) and DMSO at a volume ratio of 2:1, and prepare A series of solutions, add the competing molecule standard solution of equimolar quantity respectively, one of them adds the sodium sulfide standard solution of equimolar quantity, take 440nm as the fluorescence emission spectrum change of excitation light detection solution after 30min, by image 3 and Figure 4 As a result, it can be found that other ion pair compounds Mito-H 2 The fluorescence of S has almost no effect, and the addition of sodium sulfide solution makes the compound Mito-H 2 The fluorescence of S was significantly enhanced.
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