A kind of preparation method and application of hydrogen peroxide ratio fluorescent molecular probe based on dcpo core
A fluorescent molecular probe, hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problems of not being able to reveal the effect of hydrogen peroxide well, poor biocompatibility, short emission wavelength, etc., and achieve strong practical application value and specificity High, stable chemical properties and high effect
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Embodiment 1
[0034] Synthesis of Compound 1
[0035] At room temperature, in a 25 mL round bottom flask, DCPO (936.9 mg, 3 mmol) and hexamethylimidine (1400 mg, 10 mmol) were added to a 25 mL round bottom flask, and then 25 mL of trifluoro trifluoride was added to the reaction system. Acetic acid, warm to 90 o After the reaction is completed, remove the reaction, pour it into 500 mL of ice water after cooling, adjust the pH to about 6 with 1 mol / L NaOH solution, and precipitate a large amount of precipitates, filter, collect and wash the filter cake, After drying in vacuo, it was purified by column chromatography to obtain 810.6 mg of the product with a yield of 79.4%. 1 H NMR (400 MHz, DMSO-d 6 , ppm): δ 10.36 (s, 1H), 7.89-7.91(m, 1H), 7.79 (d, 1H, J =7.6 Hz), 7.72(d, 1H, J =16.0 Hz), 7.89-7.62 (m, 3H), 7.28 (d, 1H, J =16.0 Hz,), 6.98 (s, 1H), 6.85 (d, 1H, J =8.8 Hz), 5.56(s, 1H), 5.35(s, 1H).
[0036] Synthesis of Compound 2
[0037] Compound 1 (680.6 mg, 2 mmol) was dissolv...
Embodiment 2
[0041] Experiment on the relationship between the fluorescence intensity of fluorescent probe and the concentration of hydrogen peroxide
[0042] Accurately weigh 661.5 mg of the target fluorescent molecular probe with a purity of more than 99% prepared in Example 1, transfer it to a 50 mL volumetric flask, dissolve it in an acetonitrile solution, and prepare a 1 mM probe stock solution. Take 20 μL from the mother solution and add it to a 5 mL centrifuge tube, add hydrogen peroxide standard solutions of different concentrations, dilute with PBS buffer solution (10 mM, pH=7.4), and adjust to the concentration of the probe compound in the solution to be 10 μM, and the concentrations of hydrogen peroxide were 1 μM, 3 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, and 40 μM, respectively. After 20 min incubation at room temperature, the different concentrations were tested in 10 mm cuvettes. Fluorescence spectrum of the system. Fluorescence spectra such as figure 1 shown. The results sh...
Embodiment 3
[0044] Selectivity of fluorescent probes for hydrogen peroxide
[0045] The fluorescent probe prepared in Example 1 was mixed with six reactive oxygen species (O 2 -, NO, ClO-, tert-butanol peroxy, HO , NO 3 -), two thiol amino acids (L-cysteine, L-glutathione), a metal ion (Fe 3+ ) to respond respectively to test their response. In order to ensure the comparability of the experimental results, the whole reaction system was set at 25 o C in PBS buffer solution (10mM, pH=7.4), in the whole detection system, the concentration of probe molecules is 10 μM, the concentration of other compounds to be detected is 30 μM hydrogen peroxide, and the concentrations of other compounds are After incubation at room temperature for 20 min at 100 μM, the fluorescence spectra of different systems were detected, the fluorescence intensities at 695 nm and 510 nm were recorded and I was calculated. 695 nm / I 510 nm value of . The results are attached image 3 As shown, it is found that only...
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