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Method for preparing water-soluble mercury ion fluorescence probe on basis of rhodamine and application of water-soluble mercury ion fluorescence probe

A fluorescent probe, water-soluble technology, applied in the field of fluorescent probes, can solve problems such as limiting practical applications

Inactive Publication Date: 2016-08-24
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, they need to be performed in organic solvents or organic solvent-water solutions, which greatly limits their practical applications in physiological environments

Method used

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  • Method for preparing water-soluble mercury ion fluorescence probe on basis of rhodamine and application of water-soluble mercury ion fluorescence probe
  • Method for preparing water-soluble mercury ion fluorescence probe on basis of rhodamine and application of water-soluble mercury ion fluorescence probe
  • Method for preparing water-soluble mercury ion fluorescence probe on basis of rhodamine and application of water-soluble mercury ion fluorescence probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 5-carboxyrhodamine B (2): Add 1,2,4-trimellitic anhydride (1.92 g, 10 mmol) and 3-diethylamino to a 100 mL round bottom flask containing 50 mL N,N-dimethylformamide Phenol (3.30g, 20mmol), under the protection of nitrogen, magnetically stirred and refluxed for 6 hours, and the reaction was stopped; after the reaction mixture was cooled to room temperature, double distilled water (200mL) was added, and after fully stirring, it was carried out with dichloromethane (100mL×3) After extraction, the organic layers were combined and the solvent was distilled off under reduced pressure. The crude product was separated by column chromatography with dichloromethane / methanol at 6:1 (volume ratio) to obtain red solid 2 (0.419g, yield: 8.6%). 1 H NMR (400MHz, CD 3 OD)δ8.19(d,J=8.0Hz,1H),8.08(d,J=8.0Hz,1H),7.80(s,1H),7.28(d,J=8.0Hz,2H),6.98(d ,J=8.0Hz,2H),6.89(s,2H),3.64(d,J=8.0Hz,8H),1.28(s,12H). 13 CNMR (100MHz, CD 3 OD)δ164.9, 160.4, 157.9, 134.3, 132.8, 132.6, 13...

Embodiment 2

[0028] Fluorescent probe 1 and Hg 2+ Solution preparation for action

[0029] Dissolve a certain amount of fluorescent probe in water to obtain a concentration of 1.0×10 -4 mol L -1 Probe stock solution. Dissolve a certain amount of mercury nitrate in water, pour it into a 500mL volumetric flask, add water to dilute to the mark, and obtain a concentration of 1.0×10 -3 mol L -1 Hg 2+ . will be 1.0×10 -3 mol L -1 Hg 2+ The aqueous solution was gradually diluted with double distilled water to obtain 1.0×10 -4 -1.0×10 -8 mol L -1 Hg 2+ aqueous solution. Mix 1.0 mL of probe stock solution and 1.0 mL of Hg 2+ The aqueous solution was added to a 10mL volumetric flask, and the buffer solution Tris-HNO 3 Constant volume, to obtain a concentration of 1.0 × 10 -5 mol L -1 fluorescent probe and 1.0 x 10 -4 -1.0×10 -8 mol L -1 Hg 2+ Mix the solutions to be tested.

Embodiment 3

[0031] Fluorescent probe 1 and Hg 2+ Determination of the fluorescence spectroscopic properties of the action

[0032] Tris-HNO at pH 7.0 3 The buffer solution was used as the solvent, and the fluorescent probe and Hg were measured with a Perkin Elmer LS 55 fluorescence spectrophotometer. 2+ The fluorescence spectrum of the action, the results are as follows figure 2 . The concentration of the fluorescent probe was 10 μM, Hg 2+ The concentration is 0, 0.3, 0.5, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, 20.0μM, the excitation wavelength is fixed at 520nm, the emission wavelength range is 530-650nm, the slit width It is 5nm / 5nm. Add Hg 2+ Before, the fluorescent probe was almost non-fluorescent, adding Hg 2+ After that, the emission peak of rhodamine appeared at 573nm, and with the Hg 2+ As the concentration increases, the fluorescence intensity of the probe molecule increases continuously. When 10.0 μM Hg is added 2+ When , the fluorescence intensity increase...

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Abstract

The invention discloses a method for preparing a water-soluble mercury ion fluorescence probe on the basis of rhodamine and application of the water-soluble mercury ion fluorescence probe. A structural formula of the Hg<2+> fluorescence probe are shown, and the water-soluble mercury ion fluorescence probe is synthesized from 1, 2, 4-trimellitic anhydride, 3-diethylamino phenol and hydrazine hydrate. The method and the application have the advantages that the water-soluble Hg<2+> fluorescence probe prepared by the aid of the method is simple in structure, is based on rhodamine derivatives and is the first fluorescence probe for detecting Hg<2+> in 100% aqueous solution by the aid of rhodamine lactam derivatives; ring opening of rhodamine lactam structures can be carried out under the induction effects of the Hg<2+> in systems, intense fluorescence can be generated, and the water-soluble mercury ion fluorescence probe is high in Hg<2+> detection sensitivity; the fluorescence probe is excellent in Hg<2+> selectivity and is almost free of interference of other positive ions; the Hg<2+> can be measured by the fluorescence probe without disturbance when pH (potential of hydrogen) values range from 5.0-8.0, the fluorescence probe and the Hg<2+> can act quickly, and the response time is shorter than 3 minutes; the probe further can be applied to measuring Hg<2+> in environmental water samples and carrying out fluorescence imaging on Hg<2+> in biological cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to water-soluble Hg based on rhodamine derivatives 2+ Preparation and application of fluorescent probes. Background technique [0002] As one of the most harmful environmental pollutants, mercury ions are widely distributed in air, water and soil. It can accumulate continuously in the environment, and will be converted into lipophilic methylmercury by bacteria, and enter organisms and human body through the food chain. (Document 1: D.W.Boening, Chemosphere, 2000, 40, 1335–1351.). Moreover, mercury ions can easily pass through biological cell membranes (document 2: X. Zhang, Y. Xiao, X. Qian, Angew. Chem. Int. Ed., 2008, 47, 8025–8029.), and can interact with proteins Combination of sulfhydryl groups in (document 3: M.Harada, Crit.Rev.Toxicol., 1995,25,1–24.), will cause serious damage to the brain, kidney and nervous system (document 4: Y.Zhou, C .-Y. Zhu, X.-S. Gao, X...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 李春艳李丹李勇飞
Owner XIANGTAN UNIV
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