Near-infrared fluorescence probe used for detecting zinc ions in water phase, preparation method thereof, and application thereof
A fluorescent probe, near-infrared technology, used in fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of cell damage, detection interference, limitations, etc., and achieve the effect of good membrane permeability
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[0031] Example 1: Preparation of near-infrared fluorescent probes.
[0032] Such as figure 1 As shown, 5.6g 2-chloromethylpyridine hydrochloride, 3.24g N-3-methoxyphenyl-N-methylethylenediamine (4), 2.72g sodium hydroxide, 109mg phase transfer catalyst, 5.45 g of potassium iodide was dissolved in a mixed solution of 35 mL of water and 35 mL of tetrahydrofuran. The above solution was reacted at room temperature for 2 days under vigorous stirring. After extracting with dichloromethane, drying and evaporating the solvent, the crude product is obtained. The intermediate product N-3-methoxyphenyl-N-methyl-N',N'-bis(2-methylenepyridine)ethylenediamine (3) is obtained through silica gel column separation as a colorless oil.
[0033] The characterization data is: 1 HNMR(400MHz, CDCl 3 ): δ8.53 (d, J=4.8, 2H, 2×Ar-H), 7.63 (td, J=7.7, 1.4, 2H, 2×Ar-H), 7.50 (d, J=7.8, 2H, 2×Ar-H), 7.18-7.11(m, 2H, 2×Ar-H), 7.04(t, J=8.2, 1H, Ar-H), 6.21(d, J=8.5, 2H, 2×Ar -H), 6.17(d, J=2.0, 1H, Ar-H), 3...
Example Embodiment
[0044] Example 2: Zinc ion near infrared fluorescent probe 1 (X=ClO 4 ) Performance experiment.
[0045] The synthetic fluorescent probe was prepared into a buffer mother solution containing 1% DMSO, and then diluted with a buffer solution to the corresponding concentration, and its performance was tested.
[0046] (1) Sensitivity analysis of zinc ion fluorescent probe:
[0047] Add the fluorescent probes (1) to aqueous solutions of different concentrations of zinc ions, the probe concentration is 10×10 -6 M, by figure 2 It can be seen that the fluorescence emission intensity gradually increases after the addition of zinc ions. figure 2 Available image 3 . by image 3 It can be seen that the fluorescence intensity of the fluorescent probe and the zinc ion concentration are at 1×10 -6 M to 1×10 -5 A good linear relationship is formed in the M range, which makes it possible to quantitatively detect the zinc ion concentration.
[0048] (2) Selective analysis of zinc ion fluorescent pr...
Example Embodiment
[0050] Embodiment 3: Use the above-mentioned fluorescent probe to perform fluorescence imaging in living cells.
[0051] Fluorescent probes for the detection of zinc ions in cells Figure 5 It can be seen from the figure that the fluorescent probe can eliminate the interference of cell autofluorescence, and can be used for the detection of zinc ions in biological systems and the fluorescence imaging of zinc ions in biological living cells.
[0052] In summary, the zinc ion near-infrared fluorescent probe of the present invention is water-soluble and has good sensitivity. The pretreatment of the test sample is very simple, and the emission wavelength is in the long wavelength region, so it can be used for zinc ions in living biological cells. Detection and fluorescence imaging.
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