Preparation method and application of a ratiometric fluorescent probe for detecting hydrazine

A technology of fluorescent probes and fluorescent molecular probes, which is applied in the field of analytical chemistry, can solve the problems of limited fluorescent probes for hydrazine detection, and achieve the effect of improving detection accuracy

Active Publication Date: 2020-12-01
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reported fluorescent probes for the detection of hydrazine are still limited, and the development of probes for detecting the concentration of hydrazine in living cells under physiological conditions has great application prospects.

Method used

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  • Preparation method and application of a ratiometric fluorescent probe for detecting hydrazine
  • Preparation method and application of a ratiometric fluorescent probe for detecting hydrazine
  • Preparation method and application of a ratiometric fluorescent probe for detecting hydrazine

Examples

Experimental program
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Effect test

Embodiment 1

[0055] Example 1: Preparation of ratiometric fluorescent molecular probes

[0056] (1) Dissolve 40mL of anhydrous N,N-dimethylformamide in 40mL of dichloromethane, pour into a jacketed bottle, cool at -10°C and stir for 20 min to obtain a mixed solution 1. Dissolve 37mL of phosphorus oxychloride in 35mL of dichloromethane, mix evenly, pour into the constant pressure funnel, slowly drop into the mixed solution 1, and keep stirring with a magnetic stirrer; after the dropwise addition, add 10g of cyclohexanone Slowly add the powder into the jacketed bottle, return to room temperature when the solution turns bright yellow, then slowly heat to 40°C, and heat to reflux for 3h; Extraction, rotary evaporation to obtain compound 1;

[0057] (2) Add 50ml of benzindole and 50mL of iodoethane into a 500mL three-neck flask, add 200mL of acetonitrile, heat and reflux for 24 hours; cool to room temperature and filter, filter the precipitate and place it in a beaker after being washed with p...

Embodiment 2

[0067] Implementation Example 2: The ratiometric fluorescent molecular probe prepared in Example 1 quantitatively analyzes hydrazine in biological samples: detection of hydrazine content in water samples

[0068] 1) Prepare the solution

[0069] Probe stock solution: Accurately weigh the ratiometric fluorescent molecular probe for detecting hydrazine and dissolve it in acetate buffer and DMSO to prepare a probe stock solution with a concentration of 50 μM; the pH of the acetate buffer is 4.5, and the concentration 10mM; the volume ratio of acetate buffer and DMSO is 1:9;

[0070] Hydrazine stock solution: Accurately weigh 0.00032g of hydrazine and dissolve it in 10mL of deionized water to prepare a hydrazine stock solution with a concentration of 1000μM;

[0071] 2) Establish the linear equation of water sample-hydrazine standard

[0072] Dilute the hydrazine stock solution prepared in step 1) with distilled water to obtain a hydrazine standard solution with a gradient conce...

Embodiment 3

[0076] Implementation example 3: detection of hydrazine in liver cancer cells, the method is: put the liver cancer cells into DMEM medium and cultivate them for 24 hours, and wait until the inoculum amount of liver cancer cells in the medium is 2×10 7 ~9×10 7 Each / mL, then add the ratiometric fluorescent molecular probe for detecting hydrazine, the probe concentration is 5 μM, add 0 μM, 20 μM, 40 μM, 60 μM, 80 μM, 100 μM N 2 h 4, according to the measured fluorescence emission of the fluorescent probe, different excitation and emission wavelengths are selected, and the fluorescence image of the cell is obtained on the confocal laser scanning microscope. The fluorescence intensity at the position increases significantly, and it can be judged that the probe can detect hydrazine in living cells. (red channel 700-800 nm (λex=635nm), green channel 600-700 nm (λex=559 nm)).

[0077] Figure 5 a- Figure 5 e are the fluorescence collection windows for the red channel a) : the re...

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Abstract

The invention relates to a preparation method and application of a ratiometric fluorescent probe for detecting hydrazine. The preparation comprises the steps that phosphorus oxychloride is dissolved in dichloromethane, the mixture is slowly dropped into N,N-dimethylformamide, and after the dropwise addition is finished, cyclohexanone is added for reaction so as to obtain a compound 1; then, benzoindoles and iodoethane are dissolved in acetonitrile for heating and refluxing reaction so as to obtain a compound 2; the compound 1 and the compound 2 are subjected to heating and refluxing by takingmethylbenzene and n-butyl alcohol as solvents so as to obtain a fluorescent probe compound 3; the compound 3 is dissolved in anhydrous N,N-dimethylformamide, and sodium acetate is added for reaction under the protection condition of nitrogen so as to generate a compound 4; and the compound 4 is dissolved in anhydrous dichloromethane containing acetyl chloride, triethylamine is added for reaction for 4 hours at normal temperature under the protection of the nitrogen so as to generate the probe Ben-Cy1. ccording to the preparation method and application of the ratiometric fluorescent probe, theprobe works in a near-infrared region, is suitable for qualitative and quantitative analysis, low biotoxicity and high selectivity in biological samples and can be applied to the related fields of analytical chemistry, life organic analytical chemistry and the like.

Description

technical field [0001] The invention belongs to the field of analytical chemistry and relates to a preparation method and application of a ratiometric fluorescent probe for detecting hydrazine. Background technique [0002] Hydrazine (N 2 h 4 ) are well known as various rocket fuels and low power monopropellants due to their flammable and explosive properties. It plays an important role in chemical, pharmaceutical and agricultural industries involving catalysts, chemicals for photography, pesticides, various dyes, pharmaceutical intermediates, etc. However, hydrazine is highly toxic and exposure to high levels of hydrazine may cause severe damage to the liver, lungs, kidneys, and especially the nervous system in humans. Therefore, it is very important to develop reliable and sensitive analytical methods for the accurate detection of hydrazine. Conventional detection methods for hydrazine include electrochemical analysis, chromatography and capillary electrophoresis. How...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64G01N21/25C07D209/60C09K11/06
CPCC07D209/60C09K11/06C09K2211/1007C09K2211/1029G01N21/25G01N21/643
Inventor 陈光宋亚群于法标韩潇玥王蕊
Owner QUFU NORMAL UNIV
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