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Enhanced fluorescent probe for detection CN-(Cyanogen), preparation method and biological application thereof

A fluorescent probe and enhanced technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor photostability and high detection limit of fluorescent probes, and achieve low detection limit and high sensitivity , good selective effect

Active Publication Date: 2019-01-18
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems of high detection limit and poor photostability of existing fluorescent probes, the present invention provides a method for detecting CN - The enhanced fluorescent probe and its preparation method and biological application, the probe is an enhanced fluorescent probe for CN in vivo - Detection and Imaging

Method used

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  • Enhanced fluorescent probe for detection CN-(Cyanogen), preparation method and biological application thereof
  • Enhanced fluorescent probe for detection CN-(Cyanogen), preparation method and biological application thereof
  • Enhanced fluorescent probe for detection CN-(Cyanogen), preparation method and biological application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: A method for detecting CN - The fluorescent probe is 1-(pyrene-1-yl)-3-(N-ethylcarbazol-3-yl)propenone, and its chemical structure is as follows: .

[0022] Prepare the detection CN - The method for enhancing the fluorescent probe, using 1-acetylpyrene as a starting material, and N-ethylcarbazole-3-formaldehyde according to the ratio of 1:1 in molar ratio, then adding an appropriate amount of NaOH, stirring the reaction at room temperature, 1-(Pyren-1-yl)-3-(N-ethylcarbazol-3-yl)propenone is obtained.

[0023] Specific steps are as follows:

[0024] Add 0.2461g (1mmol) 1-acetylpyrene and 0.2231g (1mmol) N-ethylcarbazole-3-carbaldehyde into a dry 50mL single-necked flask, stir with 15mL absolute ethanol until completely dissolved into a light yellow solution , add 0.75g NaOH, stir reaction at room temperature about 4h (separation out a large amount of yellow precipitates), TLC tracking (V 乙酸乙酯 :V 石油醚 =1:3), suction filtered after the reaction, washed t...

Embodiment 2

[0028] Example 2: The fluorescent probe was prepared with 1 mM fluorescent probe stock solution in DMSO; 2.0 mL of DMSO system and 20.0 µL of fluorescent probe stock solution were added to a fluorescent cuvette, and CN was performed on a fluorescence spectrophotometer. - UV titration experiment, and record its UV absorption spectrum, the UV absorption spectrum diagram is shown in figure 1 . Depend on figure 1 It can be seen that with CN - As the amount increases, the absorption peak at 324nm decreases, while the ultraviolet absorption at 398nm increases, and the fluorescence intensity at 488nm increases.

Embodiment 3

[0029] Example 3: Fluorescent probes with CN - Fluorescence titration plot of change

[0030] Add 20.0 µL of fluorescent probe stock solution to 2.0 mL of DMSO for CN - Fluorescence titration experiment, detected on a fluorescence spectrophotometer, the probe itself has an emission peak at 545nm, such as figure 2 As shown, with CN -A new peak appeared at 488nm and gradually strengthened. Instrument parameters: The slit widths of the excitation wavelength and emission wavelength are 2.5 nm and 2.5 nm respectively, the voltage is 600 V, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex 415 nm and a maximum emission wavelength of λ em at 545 nm. Such as image 3 Shown in CN - The concentration is the abscissa, and the fluorescence intensity I 488 Plotting the graph for the ordinate gives CN - The working curve of concentration, linear regression equation is: I 488 = 6.74*[ CN - ] + 100.72, CN - The unit of concentration is 10 -6 mol...

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Abstract

The invention belongs to the technical field of synthesis of a fluorescent probe. In order to solve the problems that an existing fluorescent probe is high in detection limit and poor in photostability, the invention provides an enhanced fluorescent probe for detecting CN- (Cyanogens), a preparation method and a biological application thereof. The fluorescent probe is 1-(pyren-1-yl)-3-(N-ethyl carbazole-3-yl)acrylketone. The preparation method comprises the steps of dissolving 1-acetylpyrene and N-ethyl carbazole-3-formaldehyde in anhydrous ethanol, then adding sodium hydroxide, continuously stirring the mixture at room temperature for 4 h, precipitating a yellow solid, tracking the reaction with a TLC (Thin-Layer Chromatography), performing suction filtration after the reaction is completed, washing with anhydrous ethanol and water (1 / 1, v / v), and drying in vacuum to obtain yellow powder. The detection of the fluorescent probe for CN- is enhanced, the reaction is rapid, the selectivity and sensitivity are high, and the fluorescent probe can be used for detection of CN- in an organism in combination with a confocal laser scanning microscopy.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorescent probes, in particular to a method for detecting CN - The enhanced fluorescent probe and its preparation method and biological application, the probe is applied to the detection of cyanide in living organisms. Background technique [0002] Cyanide is a well-known and highly toxic substance that is very harmful to human health. A small amount of cyanide can lead to extremely fatal poisoning. This is because living cells absorb cyanide through the gastrointestinal tract, skin or lungs and release cyanide ions in the human body. It is caused by the inhibition of respiration of living cells by iron binding. However, cyanide is still widely used in various fields, such as gold mining, electroplating, metallurgy, synthetic fiber and resin industry. Therefore, it is necessary to develop a convenient and rapid method for the detection of cyanide ions. [0003] Fluorescence spectroscopy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCG01N21/643C09K11/06C07D209/86C09K2211/1029C09K2211/1011
Inventor 钞建宾王小露张永斌徐苗
Owner SHANXI UNIV
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