Preparation method and application of ratio type fluorescent probe for peroxynitrite
A technology of peroxynitroso and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of reducing probe sensitivity, interference, short analysis wavelength, etc., and achieve the effect of good spectral response performance
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[0025] Example 1:
[0026] Synthesis of fluorescent probe
[0027] Synthetic route such as figure 1 . Synthesis of Coumarin 334: In a 100mL round-bottom flask, combine 8-hydroxyjulonidine-9-formaldehyde (1.09g, 5mmol), ethyl acetoacetate (0.63mL, 5mmol) and piperidine (0.035mL, 0.5mmol) was dissolved in 20.0mL of dichloromethane, stirred and refluxed for 6h, the reaction was stopped, the solvent was removed by distillation under reduced pressure, and the crude product was subjected to column chromatography with dichloromethane eluent to obtain a dark yellow solid compound (0.85g, The yield is 60%), which is coumarin 334.
[0028] ONOO - Synthesis of fluorescent probe: In a 100 mL round bottom flask, dissolve coumarin 334 (0.42 g, 1.48 mmol) and 4-diethylamino keto acid (0.46 g, 1.48 mmol) into 8 mL of concentrated sulfuric acid. The reaction mixture Stir at 90°C for 12h to stop the reaction, then cool the reaction mixture to room temperature, pour it into a beaker containing 50g i...
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[0029] Example 2:
[0030] Fluorescent probe and ONOO - Solution preparation
[0031] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in methanol to make 1×10 -3 M probe solution. ONOO - The preparation of the solution: the 0.70M H 2 O 2 Solution, 0.60M HCl solution, 0.60M NaNO 2 Mix the solution, and quickly add 1.5M NaOH solution, excess H 2 O 2 It is removed with manganese dioxide and stored in a freezing environment at -20°C. Defrost before use, ONOO - To determine the concentration, it is necessary to determine the absorbance A of the solution at 302nm. The calculation formula is: C ONOO -=A / 1.67 (mM).
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[0032] Example 3:
[0033] Fluorescent probes and ONOO - Determination of the fluorescence spectrum of the effect
[0034] figure 2 For fluorescent probes and ONOO - Fluorescence spectrum of the effect, the concentration of fluorescent probe is 5μM, ONOO - The concentration is 0,1.0,2.0,4.0,6.0,8.0,10,12,14,15μM. The excitation wavelength is fixed at 440nm, and the emission wavelength range is 450-820nm. The slit width is 5.0nm / 5.0nm, and the fluorescence measuring instrument used is Hitachi F4600 fluorescence spectrophotometer. From figure 2 It can be seen that joining ONOO - Previously, the fluorescent probe had a near-infrared (720nm) fluorescence emission peak; add ONOO - After that, a green emission peak appeared in the visible region (500 nm). This is because the probe molecule is ONOO - Oxidation leads to breakage, and the conjugate structure becomes smaller, resulting in short-wavelength green fluorescence. And with ONOO - As the concentration increases, the near-infra...
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