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Mercury ion fluorescent probe and preparation method and application thereof

A fluorescent probe, mercury ion technology, applied in the field of fluorescent probes, can solve the problems of high equipment requirements, high price, and no continuous detection, and achieve the effects of simple synthesis steps, high specificity, and short reaction time

Active Publication Date: 2016-12-14
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as ultraviolet spectrophotometry, atomic absorption / emission method, biosensor method, inductively coupled plasma mass spectrometry and electrochemical method (voltammetry and polarography), etc., although the above-mentioned several traditional detection methods can be completed for different systems Mercury content detection of samples, but they have high requirements on the equipment of the instrument, are expensive, and require a large number of samples to be tested, and do not allow continuous detection. The limitations of these methods restrict the use of various samples to be tested, especially In vivo point-of-care detection and trace analysis

Method used

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  • Mercury ion fluorescent probe and preparation method and application thereof
  • Mercury ion fluorescent probe and preparation method and application thereof
  • Mercury ion fluorescent probe and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032]

[0033] Synthesis of rhodamine B hydrazide compound

[0034]Take 1.443 g (3 mmol) of Rhodamine B and transfer it into a 100 mL round bottom flask, dissolve it with 50 mL of ethanol, then pipette 3 mL (80 wt%, 20 mmol) of hydrazine hydrate aqueous solution with a pipette gun, and the reaction system is now Deep wine red, reflux reaction in an oil bath at 85°C, monitor the progress of the reaction by thin-layer chromatography (TLC), the developer is a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1, react for 6 hours and spot the plate It was found that the raw material points basically disappeared on the thin-layer plate, and the rhodamine hydrazide product point appeared at the position of about 0.5 in the ratio shift value. After slight heating, the product point was rose red. The reaction was quenched, the system was extracted with ethyl acetate, and the organic phase was collected and then distilled under reduced pressure to obtain ...

Embodiment 2

[0036]

[0037] Synthesis of o-fluororhodamine probe RFS

[0038] Take 0.1238 g (0.75 mmol) of 2-fluorophenylisothiocyanate and 0.2292 g (0.5 mmol) of rhodamine hydrazide compound and transfer them to a 25 mL round bottom flask, then add 5 mL of dry isopropanol, Magnetically stir the reflux reaction in an oil bath at 85°C, and monitor the reaction by TLC after reacting for 5 minutes. The developer is a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1. After 10 hours, the raw material point disappears, and the reaction is stopped. , after the system was lowered to room temperature, the solvent was distilled off under reduced pressure and neutral alumina was added to its dry-mixed sample, and neutral alumina was used as the stationary phase for column chromatography (petroleum ether: ethyl acetate=10:2, v / v) Separation and purification, the product is white fluffy powder ortho-fluororhodamine probe RFS (yield 82%).

Embodiment 3

[0040] Synthesis of m-fluororhodamine probe RFSM

[0041] Take 0.1238 g (0.75 mmol) of 3-fluorophenylisothiocyanate and 0.2292 g (0.5 mmol) of rhodamine hydrazide compound and transfer them to a 25 mL round bottom flask, then add 5 mL of dry isopropanol, Magnetically stir the reflux reaction in an oil bath at 85°C, and monitor the reaction by TLC after reacting for 5 minutes. The developer is a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 1:1. After 10 hours, the raw material point disappears, and the reaction is stopped. , after the system was lowered to room temperature, the solvent was distilled off under reduced pressure and neutral alumina was added to its dry-mixed sample, and neutral alumina was used as the stationary phase for column chromatography (petroleum ether: ethyl acetate=10:2, v / v) Separation and purification, the product is white fluffy powder m-fluororhodamine probe RFSM (yield 74%).

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Abstract

The invention discloses a mercury ion fluorescent probe and a preparation method and application thereof, and belongs to the technical field of fluorescent probes for environmental analysis and biological analysis and detection. Key points of the mercury ion fluorescent probe are as follows: a class of mercury ion fluorescent probe is a bottom ring modified derivative of rhodamine B, the structural formula is shown in the specification, wherein a substituent F is located at ortho-position, meta-position or para-position. The invention also discloses the preparation method of the fluorescent probe and the application of the fluorescent probe in the detection of mercury ion content in water environment systems, medicine or biological cell systems. The mercury ion fluorescent probe has the advantages of simple synthesis steps, short reaction time, high yield and easy purification, and the compound is a mercury ion fluorescence enhanced probe, is highly-specific, can work under physiological conditions, and has application prospects in biological fluorescence imaging.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes for environmental analysis and biological analysis and detection, and specifically relates to a highly selective mercury ion fluorescent probe capable of quantitatively detecting mercury ion content in a sample and its preparation method and application. Background technique [0002] Mercury is a heavy metal, commonly known as mercury. dissolved Hg 2+ It has high chemical activity and is the main form of mercury pollutants. It has strong physiological toxicity to organisms at very low concentrations. After inorganic mercury enters the environment through various channels, it is transformed into methylmercury through the action of microorganisms in the sediment, threatening the survival of aquatic organisms and causing a large number of fish poisoning or death. The toxicity of mercury can be transferred to the human body at the top of the food chain through the bioaccumulation of the f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029G01N21/64G01N21/6428
Inventor 时蕾鹿泽华麻娜娜刘统信张贵生刘青锋
Owner HENAN NORMAL UNIV
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