Hydrogen sulfide fluorescent probe and preparation method and application thereof
A technology of fluorescent probe and hydrogen sulfide, which is applied in the field of hydrogen sulfide fluorescent probe preparation, can solve the problems of biological sample destruction and limited detection sensitivity, and achieve the effects of detection, short reaction time and high yield
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Embodiment 1
[0054] Synthesis of compound 2:
[0055] Bronaphthic anhydride 1.81mmol was dissolved in 5mlDMF, followed by adding 9mmolNaN 3 , at N 2 Protected from light, heated at reflux at 90°C and stirred for 2 hours; then added water and filtered with suction to obtain Compound 2. Using pure dichloromethane as the eluent, the silica gel (200-300 mesh) chromatography column was used for purification to obtain 720 mg of light yellow solid (yield 70%), namely compound 2. The synthetic route of compound 2 is as follows:
[0056]
[0057] Synthesis of compound 3:
[0058] Dissolve 239mg of compound 2 (1mmol) in 6ml of ethanol, then add 178mmol of bete-alanine (2mmol), heat and reflux at 80°C in the dark and stir for 2h, after the reaction is completed, remove the solvent (ethanol) by suction filtration under reduced pressure to obtain crude product. Using dichloromethane and methanol at a volume ratio of 20:1 as the eluent, purification was performed on a silica gel (200-300 mesh) c...
Embodiment 2
[0067] Changes in the fluorescence spectra of the probe reacting with different equivalents of hydrogen sulfide.
[0068] Get the probe prepared in Example 1 and dissolve it in DMF to make a concentration of 1.0mmol / L probe mother solution (the concentration of the probe is 1.0mmol / L); weigh 38.9mgNa 2 Add S to 4.98ml of distilled water to prepare a sodium sulfide mother liquor with a sodium sulfide concentration of 100mmol / L. Take 30 μ L from the probe mother solution and add it to a 3mL centrifuge tube, add different equivalents (0-100eq) of sodium sulfide mother solution (the equivalent refers to the molar number of sodium sulfide in the sodium sulfide mother solution relative to the probe in the probe mother solution multiples of the number of moles), diluted to 3mL with 720 μ DMF and different volumes of PBS aqueous solution (concentration 25 mmol / L, pH 7.4), and configured as a test solution with a probe concentration of 10 μmol / L containing 25% DMF. Test the fluorescen...
Embodiment 3
[0070] Time-dependent fluorescence change of the probe with hydrogen sulfide.
[0071] Take out 30 μ L from the mother liquor of the fluorescent probe in Example 2 and add it to a 3 mL centrifuge tube, add 60 μ L of hydrogen sulfide mother solution with a concentration of 10 mmol / L, then 720 μ L of DMF and 2.25 mL of PBS aqueous solution (concentration 25 mmol / L, pH 7.4 ) was diluted to 3 mL, and prepared into a test solution with a probe concentration of 10 μmol / L, a hydrogen sulfide concentration of 0.2 mmol / L, and 25% DMF. With an excitation wavelength of 445nm, its fluorescence spectrum changing with time was tested. Depend on Figure 5 It can be seen that as time increases, the fluorescence intensity at 535 nm and 650 nm gradually increases, and reaches a stable value in about 20 minutes. Take out 30 μL from the fluorescent probe mother solution in Example 2 again and add it to a 3mL centrifuge tube, add 90 μL of hydrogen sulfide mother solution with a concentration of ...
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