A kind of multifunctional small molecule fluorescent probe, preparation method and application
A technology for fluorescent probes and small molecules, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low water solubility, complex design synthesis steps, detection limits, etc., and achieve a simple synthesis method and good application. Foreground, easy-to-operate effects
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Embodiment 1
[0034] Example 1: Synthesis of Small Molecule Fluorescent Probes
[0035] The roadmap for the synthesis of small molecule fluorescent probes is shown in figure 1 Shown, wherein EtOH is ethanol, RT is room temperature.
[0036] The following is the specific process of synthesizing small molecule fluorescent probes in this example: Dissolve 7-(diethylamino)-2-oxo-2H-methylene-3-carbaldehyde (500 mg, 2.04 mmol) in 30 mL ethanol solution, and added (E)-6-(hydrazinomethylene)naphthalene-2-ol (HN) (379 mg, 2.04 mmol) at room temperature and stirred, stirred at room temperature for 20 h, and passed the reaction mixture through a Buchner funnel Filtration and washing of the filter cake with ethanol afforded the target molecular probe CMHN as a yellow solid. It can be determined that the product is the target small molecule fluorescent probe by mass spectrometry, NMR and spectroscopy methods, and its mass spectrometry, NMR such as Figure 2-3 shown.
Embodiment 2
[0037] Embodiment 2: Ultraviolet and fluorescence spectrum of small molecule fluorescent probe to hypochlorous acid and pH response
[0038] Prepare 0.5 mL of small molecule fluorescent probe (10.0 µM) in HO 2 O (with 1% EtOH) solution. 0-20 µM hypochlorous acid solution was added dropwise to the probe solution, as Figure 4 As shown in (a), after adding hypochlorous acid to the probe solution, the absorption band at around 480 nm gradually weakens, and there is a new weak absorption peak at around 410 nm.
[0039] For fluorescence titration experiments, prepare 3 mL of small molecule probes (5 µM ) in HO 2 O (containing 1% ethanol) solution. 0-20µM hypochlorous acid solution was added dropwise to the probe solution, and the fluorescence value of the probe from 420 nm to 750 nm was measured with 400 nm as the excitation wavelength. The experimental results are shown in Figure 4(b). It can be observed that the fluorescence emission of the probe changes with the increase o...
Embodiment 3
[0042] Embodiment 3: Verification of the linear reaction speed, specific selectivity and anti-interference of small molecule fluorescent probes to hypochlorous acid
[0043] Prepare 5 mL of Molecular Probes (5 µM) in HO 2 O (containing 1% ethanol) solution. Various interference medium solutions were prepared by dissolving the corresponding salts in deionized water ( Figure 5 A-N in order is ClO - , F - , Cl - , NO 2 - , ClO 4 - , HCO 3 - , H 2 PO 4 - , SO 4 2- , S 2 o 3 2- , CO 3 2- , H 2 o 2 , GSH, Cys , 20 µM). Subsequently, equal equivalents of hypochlorous acid solution and these interfering media were added to the probe solution, respectively. Detection is carried out by fluorescence spectrum, and the ratio of fluorescence emission wavelength (F 476 / F 570 )comparing. Figure 5 (c) The results show that the fluorescence ratio of these interfering media to the probe does not change as obviously as that of hypochlorous acid, and the NO that belong...
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