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Water-soluble double-photon hydrogen sulfide fluorescent probe capable of being used for detecting hydrogen sulfide in red wine and living bodies, and preparation method and application of fluorescent probe

A fluorescent probe, hydrogen sulfide technology, applied in the field of chemical analysis and detection, to achieve the effect of high sensitivity, broad application prospects and high selectivity

Active Publication Date: 2019-06-11
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are few fluorescent probes for detecting hydrogen sulfide. Synthesizing a fluorescent probe with high sensitivity and high selectivity, which can quickly and conveniently detect hydrogen sulfide in red wine, cancer cells and tissues has important significance and practical value.

Method used

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  • Water-soluble double-photon hydrogen sulfide fluorescent probe capable of being used for detecting hydrogen sulfide in red wine and living bodies, and preparation method and application of fluorescent probe
  • Water-soluble double-photon hydrogen sulfide fluorescent probe capable of being used for detecting hydrogen sulfide in red wine and living bodies, and preparation method and application of fluorescent probe
  • Water-soluble double-photon hydrogen sulfide fluorescent probe capable of being used for detecting hydrogen sulfide in red wine and living bodies, and preparation method and application of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] This embodiment provides a method for preparing a water-soluble two-photon hydrogen sulfide fluorescent probe for red wine and in vivo hydrogen sulfide detection, comprising the following steps:

[0038] S1. Synthesis of crude product: 0.193g (1.00mmol) 4-(diethylamino)-salicylaldehyde, 0.186g 2,4-dinitrofluorobenzene (1.00mmol), 0.294g (3mmol) K 2 CO 3 and 40mL CH 3 CN was added to a 100-ml round-bottomed flask, equipped with a circulating condensing device, the mixture was stirred at 65 ° C, and the reaction was followed by thin-layer chromatography until 4-(diethylamino)-salicylaldehyde was completely reacted; the final mixture Pour into an appropriate amount of ice water, and suction filter to obtain a yellow solid. The solid is washed 3 times with cold water, and the solid is dried in a constant temperature drying oven to obtain a solid crude product that is directly used in the next reaction. The structure of the crude product is as shown in formula (II). Shown;...

Embodiment 2

[0044] The present embodiment is a probe molecular detection test, and the results are as follows: image 3 shown.

[0045] Where: (a) is the normalized UV-Vis absorption spectrum of CM-H2S and CM-H2S+Na2S.

[0046] (b) is the fluorescence spectrogram of the response of the probe molecule (1 μM) to hydrogen sulfide, hydrogen sulfide (0-35 μM), the titration experiment of the hydrogen sulfide fluorescent probe and hydrogen sulfide. Use a fluorescence spectrometer to test the fluorescence spectrum under different concentrations of hydrogen sulfide. The excitation wavelength of the fluorescence spectrum is 380nm, the emission wavelength is 500nm, and the detection wavelength is 400-650nm. With the increase of the concentration of sodium sulfide, the fluorescence intensity at 500nm wavelength Gradually enhanced, indicating that the fluorescent probe prepared by the present invention can respond to hydrogen sulfide.

[0047] (c) is the calibration curve.

[0048] (d) is a linear...

Embodiment 3

[0051] This embodiment is a selectivity test for fluorescent probes to detect hydrogen sulfide, and the results are as attached Figure 4 shown.

[0052] Under the same test conditions, the fluorescence spectrum after adding 35 micromoles of hydrogen sulfide or 100 micromoles of other analytes to 1 micromoles of probe molecules. Among them: the excitation wavelength of the fluorescence spectrum is 380nm, the emission wavelength is 500nm, and the detection wavelength is 400-650nm. The results are attached Figure 4 (a) shown.

[0053] attached by Figure 4 (a) It can be seen that numbers 1 to 16 represent blanks (probe molecules) respectively, and S 2 o 3 2- , S 2 o 4 2- , S 2 o 5 2- , SO 3- , GSH, Cys, Hcy, Na 2 S, Ca 2+ , Mg 2+ , Na + , K + , Cu 2+ , Zn 2+ , and Fe 3+ . Only hydrogen sulfide is significantly enhanced in fluorescence intensity, and other bioactive small molecules and other analytes do not interfere with the detection results, indicating th...

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Abstract

The invention belongs to the field of chemical analysis and detection, and particularly discloses a water-soluble double-photon fluorescent probe capable of being directly used for detecting hydrogensulfide in red wine, cancer cells and tissues, and a preparation method and application of the water-soluble two-photon fluorescent probe. According to the fluorescent probe, a coumarin derivative with a double-photon property is taken as a signal group, 2,4-dinitrophenyl ether is taken a hydrogen sulfide recognition group, and the structure of the fluorescent probe is represented as in a formula(I). The fluorescent probe is good in water solubility, high in selectivity, excellent in anti-interference capability and high in sensitivity, can be directly used for rapid detection of hydrogen sulfide in red wine, cancer cells and tissues, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and more specifically, relates to a water-soluble two-photon hydrogen sulfide fluorescent probe for red wine and in vivo hydrogen sulfide detection and its preparation method and application. The fluorescent probe of the invention is especially Suitable for applications in the detection of hydrogen sulfide in red wine, cancer cells and tissues. Background technique [0002] Hydrogen sulfide (H 2 S) is a toxic contaminant with a strong "rotten egg" aroma, a common wine component produced by yeast fermentation, and a typical problem in wine production and storage around the world. [0003] In recent years, as an excellent detection technology, fluorescent probes have attracted more and more attention due to their high selectivity, high sensitivity and real-time imaging, and have been widely used in the detection of various substances. Recent studies have shown that H 2 S ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/43C09K11/06G01N21/64
Inventor 周礼义
Owner HUNAN UNIV OF TECH
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