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hg based on rhodamine derivatives 2+ Fluorescent probe and its preparation method and application

A fluorescent probe and derivative technology, applied in the field of fluorescence detection, can solve the problems of narrow pH range, poor selectivity, slow response speed, etc., and achieve the effects of high accuracy, good biocompatibility and high sensitivity

Active Publication Date: 2020-09-29
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some of the reported Hg 2+ Probes have disadvantages such as slow response speed, narrow pH range, and poor selectivity

Method used

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  • hg based on rhodamine derivatives <sup>2+</sup> Fluorescent probe and its preparation method and application
  • hg based on rhodamine derivatives <sup>2+</sup> Fluorescent probe and its preparation method and application
  • hg based on rhodamine derivatives <sup>2+</sup> Fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of Compound 2: Rhodamine B (4.79g, 10mmol) was added to a dry 100mL single-necked flask, and 30mL of ethanol was added to dissolve it, and 9mL of hydrazine hydrate (85%) was added dropwise under magnetic stirring, and heated to reflux for 12h Stop the reaction, cool the mixture solution to room temperature and distill off the solvent under reduced pressure, add 50mL of 1mol / L hydrochloric acid solution, then adjust its pH value to neutral with 1mol / L sodium hydroxide solution; add dichloromethane for extraction, Extracted three times, adding 30 mL each time, collected the dichloromethane phase, spin-dried the solvent, and dried to obtain 3.92 g of compound 2 as a khaki solid, with a yield of 86%.

[0058] Synthesis of Compound 3: Add Compound 2 (1.08 g, 2.4 mmol), Lowe’s Reagent (0.96 g, 2.4 mmol) and redistilled 40 mL of toluene to a 100 mL round-bottomed flask under nitrogen flow, and heat to reflux under magnetic stirring for reaction 4 Hour, after the mixt...

Embodiment 2

[0065] The measurement of embodiment 2 fluorescence intensity

[0066] A certain amount of compound 1 was dissolved in ethanol to obtain 1.0×10 -5 mol / L stock solution of compound 1.

[0067] Diluted step by step with 0.05mol / L Tris–HCl buffer solution of pH 7.24 1.0×10 -2 mol / L mercury nitrate solution to get 8×10 -7 -1.0×10 -3 mol / L Hg 2+ stock solution.

[0068] Precisely measure 12.50mL stock solution of compound 1 and 2.50mL of different concentrations of Hg 2+ Add the solution into a 25mL volumetric flask, and then dilute to 25mL with 0.05mol / L Tris-HCl solution. The solution thus obtained contained 5 x 10 -6 mol / L compound 1 and 8×10 -8 -1×10 -4 mol / L Hg 2+ solution, a blank solution of compound 1 was prepared under the same conditions, but without the addition of Hg 2+ . All solutions were stored at 4°C in the dark for future use.

[0069] When measuring the fluorescence intensity, the excitation wavelength is fixed at 520nm, the incident and exit slits ar...

Embodiment 3

[0081] Influence experiment of embodiment 3pH

[0082] The influence of different pH values ​​(2.0-12.0) on the fluorescence intensity of compound 1 is detected, and the results are shown in Image 6 , Image 6 is a plot of the fluorescence emission intensity of compound 1 (5 μM) versus pH.

[0083] from Image 6 It can be seen that the fluorescence intensity of compound 1 remains basically unchanged when the pH is between 4.5 and 12.0, which indicates that the fluorescent probe is not affected by pH at pH 4.5-12.0 and can be used for the detection of actual samples. When the pH is less than 4.5, the fluorescence intensity value of compound 1 increases with the decrease of pH, which may be due to the ring-opening of the spirolactam structure of compound 1 under acidic conditions resulting in enhanced fluorescence.

[0084] Considering sensitivity, response time and practical application comprehensively, this application selects Tris-HCl buffer solution with pH 7.24 as the o...

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Abstract

The invention provides a Hg2+ fluorescence probe based on a rhodamine derivative. The probe is of a structure shown in the formula I. The fluorescence probe based on rhodamine compounds is used for Hg2+ detection. The probe can detect Hg2+ in a n ethyl alcohol / water solution with the pH being 4.5-12.0 and v:v being 1:1,and the probe has the advantages of being high in sensitivity,good in selectivity and the like. When Hg2+ exists,while the fluorescent transmission intensity of the probe is enhanced,the color of the solution changes from colorless to pink,the Hg2+ linear response range of the probe is 8.0*10<-8>-1.0*10<-5> mol / L,and the lower detection limit is 3.0*10<-8> mol / L. Experiment results show that the probe is high in river water and tap water Hg2+ recycling rate measuring resultaccuracy,the probe has the better biological compatibility and can be used for Hg2+ fluorescence imaging detection inside living cells.

Description

technical field [0001] The invention relates to the technical field of fluorescence detection, in particular to a rhodamine derivative-based Hg 2+ Fluorescent probes and their preparation methods and applications. Background technique [0002] Mercury is a heavy metal element that exists in nature in various forms, such as free, inorganic and organic mercury. Divalent mercury ion (Hg 2+ ) than monovalent mercury ion (Hg + ) is more common, highly corrosive and carcinogenic, and is one of the common environmental pollutants. Organic mercury, especially methylmercury, can accumulate in marine organisms and can be transferred to the human body through the food chain, causing brain damage and other chronic diseases. The most typical example is the Minamata disease that occurred in Japan. Therefore, it is urgent to establish an efficient, fast, simple and sensitive method for detecting and identifying trace amounts of mercury in the environment and in organisms. [0003] At ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/78
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643G01N21/6486G01N21/78
Inventor 麻秋娟徐俊红朱鑫胡亚楠刘庆普白玉王春燕
Owner HENAN UNIV OF CHINESE MEDICINE
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