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A kind of fluorescent probe and its preparation and application

A technology of fluorescent probe and reflux reaction, applied in the field of fluorescent probe and its preparation and application, can solve the problems of simple synthesis, high yield, change, etc., and achieve the effect of cheap raw materials, high yield, and simple preparation method

Active Publication Date: 2021-07-20
DONGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a fluorescent probe and its preparation and application, which overcomes the poor selectivity of the existing 8-hydroxyquinoline fluorescent probe in the prior art, and various metal ions can cause fluorescence. The defect of the change of the signal, the fluorescent probe involved in the present invention is to introduce the benzothiazolyl regulation and control selectivity in the 8-hydroxyquinoline structure, the fluorescent probe obtained has high selectivity to the cadmium ion, and the synthetic simple yield High, can work under the aqueous environment condition of physiological pH 7.4, has the application prospect of bioluminescence imaging and highly selective fluorescence detection of cadmium ions in environmental water samples

Method used

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  • A kind of fluorescent probe and its preparation and application
  • A kind of fluorescent probe and its preparation and application
  • A kind of fluorescent probe and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of fluorescent probes:

[0035] (1) Synthesis of 5,7-dialdehyde-8-hydroxyquinoline: 8-hydroxyquinoline (1.0g) and hexamethylenetetramine (2.0g) were dissolved in trifluoroacetic acid (10.0mL), Reflux at 110°C for 72 hours, remove the solvent by rotary evaporation, wash with dilute hydrochloric acid, filter, wash the solid with water until neutral, and dry in vacuo to obtain 5,7-dialdehyde-8-hydroxyquinoline with a yield of 82%.

[0036] 1 H NMR(400MHz,DMSO),δ(ppm):10.46(s,1H),10.04(s,1H),9.83(dd,J=1.44,8.59Hz,1H),8.97(dd,J=1.44,4.72 Hz,1H),8.40(s,1H),8.05(dd,J=4.73,8.60Hz,1H); 13 C NMR(100MHz,DMSO),δ(ppm):191.75,188.03,166.85,145.10,139.27,138.28,138.16,130.36,126.77,119.13,116.67.ESI-MS:m / z cald for C 11 h 7 NO 3 ,201.18; found: [M-H] - :200.1.

[0037] (2) Synthesis of fluorescent probes: 5,7-dialdehyde-8-hydroxyquinoline (0.1g) and o-aminothiophenol (0.15g) were dissolved in 80mL ethanol, N 2 Under protection, reflux at 85° C. for 72 h, cool to room...

Embodiment 2

[0041] Selectivity of fluorescent probes for fluorescence detection of cadmium ions:

[0042] Tris-HCl buffer solution with pH=7.4 was used to control the experimental conditions.

[0043] In different 10ml colorimetric tubes, add 0.1ml of fluorescent probe dimethyl sulfoxide solution (1mM), 2mL aqueous solution of metal ions to be tested (all metal ion concentrations are 1mM), and dilute to 10mL with Tris-HCl buffer solution , placed for 1 hour. Transfer 3mL of the working solution to a 1cm fluorescence cuvette to measure the fluorescence spectrum, the excitation wavelength is 313nm. In the blank experiment, no metal ions were added to the above solution. Selective detection of cadmium ions such as figure 2 shown. Visible fluorescence is significantly enhanced only in the presence of cadmium ions, indicating the high selectivity of the fluorescent probe involved in the present invention to cadmium ions.

Embodiment 3

[0045] Quantitative fluorescent detection of cadmium ions by fluorescent probes:

[0046]Add 0.1mL fluorescent probe dimethyl sulfoxide solution (1mM) and 0-0.1mL different volumes of 1mM cadmium ion aqueous solution to different 10ml colorimetric tubes respectively, and dilute to 10mL with Tris-HCl buffer solution, place 1h. After constant volume, the concentration of the fluorescent probe is 10 μM, and the concentration of cadmium ions is 0-10 μM. Transfer 3mL of the working solution to a 1cm fluorescence cuvette to record the fluorescence spectrum and read and record the fluorescence intensity at 526nm. Input the fluorescence intensity and corresponding cadmium ion concentration data into the software Origin8 for fitting, and get a linear working curve in the range of cadmium ion concentration 0-5μM, and the regression equation is Y=1.75309×10 11 X+149270.0393, Y is the fluorescence intensity, X is the concentration of cadmium ions, and the linear regression constant is 0...

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Abstract

The invention relates to a fluorescent probe and its preparation and application. The structure of the probe is as formula I. Preparation: Dissolve 5,7-dialdehyde-8-hydroxyquinoline and 2-aminothiophenol in a solvent, reflux reaction, and purify to obtain that product. The fluorescent probe of the present invention is simple to synthesize, has high reaction yield, is highly selective to cadmium ions, and has no obvious interference with other common ions; it can work under the environmental conditions of an aqueous solution with a physiological pH of 7.4, and has applications in bioluminescence imaging prospect.

Description

technical field [0001] The invention belongs to the field of probes and their preparation and application, in particular to a fluorescent probe and its preparation and application. Background technique [0002] Cadmium ions are typical toxic heavy metal ions that can cause permanent damage to the nervous system of organisms. Heavy metal pollution has become one of the major pollution sources in the current environmental pollution. Therefore, the development of selective detection methods for cadmium ions is of great significance to the monitoring of heavy metal pollution in water environment. The molecular fluorescent probe method has attracted much attention due to its characteristics of simplicity, rapidity, high sensitivity, good selectivity, easy automation and visual imaging. However, the development of fluorescence-enhanced fluorescent probes is still challenging due to the intrinsic property of quenching fluorescence emission of heavy metal ions. 8-Hydroxyquinoline ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/643G01N21/6486
Inventor 张煊鲁珍妮
Owner DONGHUA UNIV
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