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Preparing and application of a reactive mercury ion fluorescence probe

A fluorescent probe and mercury ion technology, applied in fluorescence/phosphorescence, analysis through chemical reaction of materials, luminescent materials, etc., can solve problems such as background interference, complicated preparation, poor water solubility, etc. The effect of simple processing and simple steps

Inactive Publication Date: 2017-01-11
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the problems of complex preparation, poor water solubility and serious background interference existing in the existing fluorescent probes, the present invention provides a porphyrin with ethylenediaminethiourea derivatives as reactive groups and porphyrin molecules as fluorescent chromophores. Phenyl-thiourea water-soluble mercury ion fluorescent probe and its preparation method, and the application of the probe molecule in the detection of mercury ion in water bodies and cells

Method used

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  • Preparing and application of a reactive mercury ion fluorescence probe
  • Preparing and application of a reactive mercury ion fluorescence probe
  • Preparing and application of a reactive mercury ion fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Tetraphenylporphyrin (TPP) (800 mg, 1.31 mmol) was dissolved in trifluoroacetic acid (50 mL), and sodium sulfite (100 mg, 1.45 mmol) was added. After reacting at room temperature for 3 min, 500 mL of water was added to quench the reaction. The reaction solution was extracted with dichloromethane, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and distilled water, respectively, and rotary evaporated to obtain a purple solid. Silica gel column separation, dichloromethane as the developing solvent, to collect the second color band product. The solvent was evaporated to dryness by rotary evaporation, and concentrated hydrochloric acid (50 mL) and stannous chloride (1100 mg, 4.875 mmol) were continuously added. The mixture was heated to 65° C., and reacted for 1 h under the protection of argon, and then 500 mL of distilled water was added. Add ammonia water to neutralize to pH 8. The reaction liquid was extracted with dichloromethane, ...

Embodiment 2

[0056] Tetraphenylporphyrin (TPP) (800 mg, 1.31 mmol) was dissolved in trifluoroacetic acid (50 mL), and sodium sulfite (100 mg, 1.45 mmol) was added. After reacting at room temperature for 3 min, 500 mL of water was added to quench the reaction. The reaction solution was extracted with dichloromethane, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and distilled water, respectively, and rotary evaporated to obtain a purple solid. Silica gel column separation, dichloromethane as the developing solvent, to collect the second color band product. The solvent was evaporated to dryness by rotary evaporation, and concentrated hydrochloric acid (50 mL) and stannous chloride (1100 mg, 4.875 mmol) were continuously added. The mixture was heated to 65° C., and reacted for 1 h under the protection of argon, and then 500 mL of distilled water was added. Add ammonia water to neutralize to pH 8. The reaction liquid was extracted with dichloromethane, ...

Embodiment 3

[0062]Tetraphenylporphyrin (TPP) (800 mg, 1.31 mmol) was dissolved in trifluoroacetic acid (50 mL), and sodium sulfite (100 mg, 1.45 mmol) was added. After reacting at room temperature for 3 min, 500 mL of water was added to quench the reaction. The reaction solution was extracted with dichloromethane, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and distilled water, respectively, and rotary evaporated to obtain a purple solid. Silica gel column separation, dichloromethane as the developing solvent, to collect the second color band product. The solvent was evaporated to dryness by rotary evaporation, and concentrated hydrochloric acid (50 mL) and stannous chloride (1100 mg, 4.875 mmol) were continuously added. The mixture was heated to 65° C., and reacted for 1 h under the protection of argon, and then 500 mL of distilled water was added. Add ammonia water to neutralize to pH 8. The reaction liquid was extracted with dichloromethane, a...

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Abstract

The invention discloses a reactive mercury ion fluorescent probe and a preparing method as well as application thereof. The method comprises the following steps: (1) 5-aminophenyl and 10, 15, 20- trisulfonate phenyl porphyrin (PNH2) is dissolved in distilled water to form solution of 7.5 mg / ml. The triphosgene is dissolved in dichloromethane to form solution of 5 MuL / mL. After the two is mixed at equal volume, react at room temperature for 3 to 5 hours and then purified, resulted to 5 -phenyl isothiocyanate base and 10, 15, 20 - trisulfate phenylporphyrin (PNCS); (2) 5 - phenyl isothiocyanate base and 10, 15, 20 - trisulfate phenylporphyrin (PNCS) and ethylenediamine derivatives are mixed in an equimolar ratio and dissolved in a mixed solvent of acetone and distilled water, to form a total concentration of 20 mg / mL solution. Finally, the solution reacts at room temperature for 6-10 hours, and after purification, the final product porphyrin-thiourea (PT) is obtained. The probe has good water solubility and shows high sensitivity and selectivity for mercury ions, and shows significant colors and fluorescence changes when detecting mercury ions. Combined with laser confocal scanning microtechnique, the probe can also be obtained the detecting imaging of the mercury ion within living cells.

Description

technical field [0001] The present invention relates to the preparation of a reactive mercury ion fluorescent probe, in particular to a porphyrin-thiourea (PT) class that uses ethylenediamine thiourea derivatives as reactive groups and porphyrin molecules as fluorescent chromophores A preparation method of a water-soluble mercury ion fluorescent probe, and the application of the probe molecule to the sensitive detection of mercury ions in aqueous solution and cells. Background technique [0002] Mercury is a heavy metal with severe physiological toxicity, which can cause serious harm to the human body and the ecological environment. Even at very low concentrations, it can also cause considerable toxicity to humans, animals and plants. The most typical example is the Minamata disease that occurred in Japan, which had an extremely bad impact on the entire society. Based on the above reasons, mercury is prioritized on the list of the Global Environmental Monitoring System (GEM...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64G01N21/78
CPCC07D487/22C09K11/06C09K2211/1029C09K2211/1074G01N21/6428G01N21/6486G01N21/78
Inventor 吕媛媛顾伟黄文斌孙晓译宣贵达王俊波
Owner ZHEJIANG UNIV CITY COLLEGE
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