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Fluorescent probe for detecting hypochlorite aions, and preparation method thereof

A technology for detecting hypochlorous acid and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of high selectivity, good water solubility, and fast reaction time

Inactive Publication Date: 2013-03-27
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yi Zhou et al. (Y.Zhou, et al, Chem.Commun., 2012, 48, 4677–4679) disclosed a dihydrofluorescein ester derivative whose fluorescence increases after hypochlorous acid oxidation, but the reaction takes 2 hours

Method used

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  • Fluorescent probe for detecting hypochlorite aions, and preparation method thereof
  • Fluorescent probe for detecting hypochlorite aions, and preparation method thereof
  • Fluorescent probe for detecting hypochlorite aions, and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The synthetic route of fluorescent probe is as follows: figure 1 shown.

[0025] Fluorescein hydrazide was refluxed with fluorescein (1g) and excess hydrazine hydrate (3ml) in 30ml of ethanol for 5 hours. After the ethanol was removed by rotary evaporation, the product was washed with distilled water, and 900mg of the product was obtained by suction filtration, with a yield of 86.5%. ESI-MS(M+H) + :m / zcalcd 347.1; found 347.0.

[0026] The synthesis steps of fluorescent probe 1 with the structure shown in formula I are as follows: fluorescein hydrazide (346 mg) and phenyl isocyanate (0.3 mL) were dissolved in 5 mL of dry N, N-dimethylformamide, and stirred overnight at room temperature for reaction. Then, 20 mL of distilled water was added to the above solution, and extracted three times with 20 mL of dichloromethane, the separated organic phase was washed with distilled water and dried over anhydrous sodium sulfate, and then the dichloromethane was removed with a rot...

Embodiment 2

[0029] The selectivity of the fluorescent probe shown in formula I to the fluorescence detection of hypochlorite.

[0030] The 10mM PBS buffer solution with pH=7.4 was used to control the experimental conditions to meet the physiological environmental conditions.

[0031] Add 0.1ml of fluorescent probe 1 ethanol solution (1mM), 8.0ml of PBS buffer solution, 0.3ml of the analyte (in which the concentration of freshly prepared sodium hypochlorite is 1mM, and the concentration of the rest of the analyte Both are 10mM), and dilute to 10ml with PBS buffer solution. After constant volume, the concentration of the probe is 10M, the concentration of hypochlorite is 30M, and the other analytes are all 300M. Shake well, and after equilibrating for 3 minutes, transfer 3ml of the working solution to a 1cm fluorescent dish to measure the fluorescence spectrum. The excitation and emission wavelengths are 480nm and 525nm, respectively. In the blank experiment, no analyte was added to the a...

Embodiment 3

[0033] Quantitative fluorescent detection of hypochlorite by fluorescent probe shown in formula I.

[0034]Add 0.1ml of fluorescent probe 1 ethanol solution (1mM), 8.0ml of PBS buffer solution, 0-1.0ml of 1mM sodium hypochlorite solution in different volumes to a series of 10ml colorimetric tubes, and dilute to 10ml with PBS buffer solution. After constant volume, the concentration of the probe is 10M, and the concentration of hypochlorite is 0-100M. Shake well, and after equilibrating for 3 minutes, transfer 3ml of the working solution to a 1cm fluorescent dish to read and record the fluorescence intensity at 525nm. The fluorescence intensity and the corresponding hypochlorite concentration data were input into the software Origin8 for fitting, and a linear working curve was obtained in the range of sodium hypochlorite concentration of 0.67-1.8M, and the linear regression constant was 0.9964, indicating that the probe can quantitatively detect the concentration of hypochlorit...

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Abstract

The invention relates to a fluorescent probe for detecting hypochlorite aions. A preparation method of the fluorescent probe comprises the steps of refluxing and reacting fluorescein and hydrazine hydrate in ethanol to generate fluorescein hydrazide; then reacting fluorescein hydrazide with phenyl isocyanate in N,N-dimethyl formamide at a room temperature, and purifying by silica gel column chromatograph to obtain a fluorescein amide phenylurea fluorescent probe. The fluorescent probe has good water-solubility, fast reaction time and high selectivity, has high specificity for the hypochlorite aions, can work at a physiological environment condition with a pH value of 7.4, and has prospects for applications in bioluminescent imaging.

Description

technical field [0001] The invention belongs to the field of fluorescent probes and preparation thereof, in particular to a fluorescent probe for detecting hypochlorite and a preparation method thereof. Background technique [0002] Hypochlorous acid (HOCl) is one of the reactive oxygen species with important physiological significance, and under the acidity of the physiological environment (pH ~ 7.4), the main hypochlorite ion (ClO - ) form exists. Although hypochlorite plays an important role in sustaining life, it is harmful if the concentration is too high. Therefore, it is of great significance to develop a rapid quantitative detection method for hypochlorite under physiological environmental conditions. The fluorescent probe method has attracted much attention because of its high sensitivity, good selectivity, and easy automation and visualization. Ma Huimin and others invented a fluorescent probe of N-benzoylrhodamine B hydrazine (Ma Huimin, Chen Xinqi, 2008, patent...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 张煊
Owner DONGHUA UNIV
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