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Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide

A fluorescent probe and carbazole-based technology, applied in the field of fluorescent probes, can solve problems such as poor anti-interference ability, sample destruction, and low accuracy, and achieve the effects of low cost, low detection limit, and high sensitivity

Active Publication Date: 2018-11-20
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have unbreakable disadvantages in their respective ranges of use, such as low accuracy, low sensitivity, complex processing, poor anti-interference ability, and destructive to samples, etc.

Method used

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  • Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide
  • Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide
  • Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0022] The preparation of embodiment 1 fluorescent probe

[0023] (1) Synthesis of 3-acetyl-N-ethylcarbazole: Dissolve 9.75g (0.05mol) N-ethylcarbazole in 150mL CH 2 Cl 2 , cooling in an ice-water bath and magnetic stirring, quickly add 8.00g (0.06mol) of anhydrous AlCl3, after stirring evenly, slowly add 5.30mL (0.075mol) of acetyl chloride dropwise, after the addition, react at room temperature for 4 hours, treat with ice water, dichloro Extract with methane, adjust the pH value of the organic layer to neutral with saturated sodium carbonate solution, then dry with anhydrous magnesium sulfate, filter with suction, and rotate the filtrate to obtain a green solid powder. The pure product was obtained by recrystallization from ethanol.

[0024] (2) Synthesis of 3-chloro-3-[3-(9-ethylcarbazolyl)]acrolein: slowly drop phosphorus oxychloride (1.395ml, 5mmol) into DMF (15ml ) solution, then remove the ice-water bath and stir for 30 minutes. 3-Acetyl-N-ethylcarbazole (1,1885 g, ...

Embodiment 2

[0028] Example 2 Fluorescent probe with H 2 UV-Vis absorption spectrum of S concentration change: Add 20.0 µL fluorescent probe stock solution to 2.0 mL PBS buffer / DMSO (4 / 6, v / v, pH 7.4) system for H 2 S ultraviolet titration experiment, and record ultraviolet-visible absorption spectrum ( figure 1 ). With H 2 With the increase of S concentration, the absorption peak of the probe at 435 nm gradually decreases, and the absorption peak at 500 nm gradually increases, and the color of the solution changes from yellow to pink at the same time, indicating that the probe can realize the "naked-eye" detection of H 2 S.

Embodiment 3

[0029] Embodiment 3 Fluorescent probe with H 2 Fluorescence emission spectrum of S concentration change: add 20.0 µL fluorescent probe stock solution to 2.0 mL PBS buffer / DMSO (4 / 6, v / v, pH 7.4) system for H 2 S Fluorescence titration experiment, detected on a fluorescence spectrophotometer. With H 2 With the increase of S concentration, the fluorescence intensity at 577 nm gradually weakened ( figure 2 ). At the same time, the fluorescence color of the solution changed from orange to blue under the irradiation of 360nm ultraviolet lamp. Instrument parameters: the slit widths of the excitation wavelength and emission wavelength are 10 nm and 10 nm respectively, the voltage is 600 V, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex 445 nm and a maximum emission wavelength of λ em 577nm. with H 2 S concentration is the abscissa, and the fluorescence intensity at 577 nm is the ordinate to draw a graph to obtain H 2 The working curve of S ...

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Abstract

The invention belongs to the technical field of a fluorescent probe, and provides synthesis and application of a colorimetric carbazole fluorescent probe for detecting hydrogen sulfide. The fluorescent probe is 5-chlorine-2-cyano-5-[3-(9-ethyl carbazole)] penta-2,4-ethyl dienoate. 3-acetyl-N-ethyl carbazole is synthesized by using N-ethyl carbazole as a raw material; 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde is synthesized; and the 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde and ethyl cyanoacetate are dissolved into absolute ethyl alcohol, a catalyst piperidine is added to performa reaction and obtain a crude product, and the crude product is dried to recrystallize the absolute ethyl alcohol, thereby obtaining the fluorescent probe. The probe reacts with the hydrogen sulfide to cause changes of a fluorescence signal and a solution color, and naked eye detection on the hydrogen sulfide can be implemented. The probe has excellent selectivity, is high in detection sensitivity, has a detection limit of 0.16 muM, and can be used for detecting the hydrogen sulfide in cells and chlorella by combining a laser confocal scanning microscopical technique.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to the synthesis and application of a colorimetric carbazole fluorescent probe for detecting hydrogen sulfide. The probe belongs to the carbazole fluorescent probe, and the probe is applied to the detection of hydrogen sulfide in cells and chlorella. Background technique [0002] Hydrogen sulfide (H 2 S) is the third endogenous gas signal molecule that can have physiological effects in the living body after carbon monoxide and nitric oxide. Hydrogen sulfide plays a role in information transmission for changes in physiological and pathological mechanisms in the nervous system, cardiovascular system and immune system of organisms. Most of the hydrogen sulfide in animals is produced from sulfur-containing amino acids such as methionine, cysteine ​​and homocysteine ​​as substrates under the catalysis of cystathionine synthase and cystathionine lyase . An appro...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64G01N21/78
CPCC07D209/86C09K11/06G01N21/6486G01N21/783
Inventor 钞建宾徐苗张永斌王小露
Owner SHANXI UNIV
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