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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

Active Publication Date: 2012-07-25
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most zinc ion fluorescent probes have the following disadvantages: 1. Some fluorescent molecular probes have poor solubility in aqueous solution, and can only show good performance in organic solvents or mixed solvents (see: (a) Natali, M .; Sol di, L.; Giordani, S. Tetrahedron. 2010, 66, 7612; (b) Helal, A.; Kim, H.-S. Tetrahedron Letters. 2009, 50, 5510.)
2. Most of the fluorescent probe molecules that recognize zinc ions are in the short-wavelength region, which will cause damage to cells when excited, and their emission wavelengths are in the ultraviolet or visible region. Autofluorescence in organisms also seriously interferes with the detection. Sensitive to pH changes, which limits its application

Method used

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  • Near-infrared fluorescence probe used for detecting zinc ions in water phase, preparation method thereof, and application thereof
  • Near-infrared fluorescence probe used for detecting zinc ions in water phase, preparation method thereof, and application thereof
  • Near-infrared fluorescence probe used for detecting zinc ions in water phase, preparation method thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of near-infrared fluorescent probes.

[0032] Such as figure 1As shown, 5.6g 2-chloromethylpyridine hydrochloride, 3.24g N-3-methoxyphenyl-N-methylethylenediamine (4), 2.72g sodium hydroxide, 109mg phase transfer catalyst, 5.45g of potassium iodide was dissolved in a mixed solution of 35mL of water and 35mL of tetrahydrofuran, and the above solution was reacted at room temperature for 2 days under vigorous stirring. Extracted with dichloromethane, dried, and evaporated to remove the solvent to obtain a crude product. The intermediate product N-3-methoxyphenyl-N-methyl-N',N'-bis(2-methylenepyridine)ethylenediamine (3) was obtained by 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),...

Embodiment 2

[0044] Example 2: Zinc ion near-infrared fluorescent probe 1 (X=ClO 4 ) performance experiment.

[0045] The synthesized fluorescent probe was made into a buffer mother solution containing 1% DMSO, and then diluted to a corresponding concentration with a buffer solution to test its performance.

[0046] (1) Sensitivity analysis of zinc ion fluorescent probe:

[0047] The fluorescent probe (1) was added to aqueous solutions of different concentrations of zinc ions, and the probe concentration was 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 . Depend on image 3 It can be seen that the fluorescence intensity of the fluorescent probe is related to the zinc ion concentration at 1×10 -6 M to 1×10 -5 In the range of M, a good linear relationship is formed, which makes it possible to quantitatively detect the concentration of zinc ions.

[0048] (2) Selective...

Embodiment 3

[0050] Example 3: Fluorescence imaging in living cells using the above-mentioned fluorescent probes.

[0051] Fluorescent probes for the detection of intracellular zinc ions see 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 living biological cells.

[0052] In summary, the zinc ion near-infrared fluorescent probe of the present invention is water-soluble, has good sensitivity, and the pretreatment of the detection sample is very simple, and the emission wavelength is in the long wavelength region, so it can be used to detect zinc ions in living cells. Detection and fluorescence imaging.

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Abstract

The invention belongs to the field of micro-molecular fluorescence probe, and especially relates to a near-infrared fluorescence probe used for detecting zinc ions in a water phase, a preparation method thereof, and an application thereof in biological living cell detections. The structural formula of the near-infrared fluorescence probe used for detecting zinc ions in the water phase is represented by the following, wherein X is halogen, perchlorate, nitrate, or bisulfate. When the fluorescence probe provided by the invention is subject to a reaction in a water phase with zinc ions, the fluorescence emission intensity is enhanced. Therefore, the probe is advantaged in good selectivity, high sensitivity, and the like. The emission peak of the fluorescence spectrum is in the near-infrared zone, such that the probe is advantaged in low cytotoxicity and good cell membrane permeability. The fluorescence probe provided by the invention can be used in intracellular zinc ion detection and fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of small-molecule fluorescent probes, in particular to a near-infrared fluorescent probe for detecting zinc ions in water phase, a preparation method thereof and the application of the fluorescent probe in the detection of biological living cells. Background technique [0002] As one of the essential trace elements for the human body, zinc plays an important role in various physiological activities in the human body, and can be used as a cofactor to regulate the activity of proteins or enzymes. Zinc deficiency can cause nerve growth and development to be hindered, and it can lead to retardation of sexual organ development. However, many experiments and epidemiological investigations have confirmed that an excessively high content of the trace element zinc, which has important physiological effects, in the human body will become harmful. Therefore, the quantitative detection of zinc ions in living systems has become t...

Claims

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Application Information

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IPC IPC(8): C07D413/14C09K11/06G01N21/64
Inventor 路建美张欠欠葛健锋孙如王丽华
Owner SUZHOU UNIV
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