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A Ratiometric Fluorescent Probe for Detecting Hydrogen Sulfide and Its Application

A ratiometric fluorescent probe, hydrogen sulfide technology, applied in fluorescence/phosphorescence, organic chemistry, luminescent materials, etc., to achieve fast response, strong selectivity, and broad application prospects

Inactive Publication Date: 2017-05-10
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, how to select donors and acceptors to make FRET more efficient, how to improve the selectivity and sensitivity of recognition molecules and improve other application properties (such as response time, stability, membrane permeability, low toxicity, etc.) no rules yet
Based on this, there are no reports on ratiometric fluorescent probes and their applications for the detection of hydrogen sulfide based on the FRET mechanism.

Method used

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  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Sulfide and Its Application
  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Sulfide and Its Application
  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Sulfide and Its Application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 The preparation of the ratio fluorescent probe (CPC) that detects hydrogen sulfide according to the present invention:

[0039] Step (a) is specifically:

[0040] Under ice-salt bath, dissolve 4-piperazinylbenzaldehyde (0.118g, 0.618mmol) in 20mL dry dichloromethane, add 0.3mL triethylamine, and add 7-diethylamino-3 - Coumarinyl chloride (0.157g, 0.562mmol), stirred for 0.5h, removed the ice-salt bath, reacted at room temperature for 3h, monitored by TLC, the reaction was complete. The solvent was distilled off under reduced pressure, using DCM:MeOH=50:1 as the developing solvent, and silica gel column chromatography gave the compound represented by formula (II) (0.140 g, 89.1%), melting point: 195-197°C.

[0041]

[0042] H NMR spectrum determination: 1 H NMR (300MHz, d-DMSO): δ9.73(s, 1H), 8.02(s, 1H), 7.74(d, J=9Hz, 2H), 7.51(d, J=9Hz, 1H), 7.06( d, J=9Hz, 2H), 6.76(dd, J=9, 2.4Hz, 1H), 6.57(d, J=2.4Hz, 1H), 3.72-3.46(m, 12H), 1.14(t, J= 7.2Hz,6H)...

Embodiment 2

[0052] Embodiment 2 fluorescent probe CPC selectively detects hydrogen sulfide

[0053] Add 10 equivalents of H to the solution of PBS buffer (0.2M, pH=7.4) containing 10mL of prepared fluorescent probe CPC with a micro-syringe. 2 S and 20 equivalents of Cl - ,CH 3 CO 2 - ,N 2 h 4 , SO 3 2- ,Br - , HCO 3 - , SO 4 2- ,EDA,CH 3 NH 2 ,CO(NH 2 ) 2 ,CS(NH 2 ) 2 ,H 2 o 2 ,NH 3 .H 2 O, I - ,HClO,GSH,Hcy,Cys,NO,O 2 - , K + , Na + , Ca 2+ After 3 hours, the aqueous solution was tested by UV-Vis spectrophotometry and fluorescence spectrophotometry (excitation wavelength is 410nm), and the results are shown in figure 2 , 3.

Embodiment 3

[0054] Embodiment 3 fluorescent probe CPC is tested to hydrogen sulfide titration

[0055] Prepare a solution of 10 mL of fluorescent probe CPC (5 μM) in PBS buffer (0.2 M, pH=7.4), add hydrogen sulfide (0-11 equivalents) to it successively, such as Figure 4 As shown, the excitation wavelength is 410nm, the fluorescence of the probe at 587nm gradually weakens, and the fluorescence at 474nm gradually increases. The response of the probe to hydrogen sulfide is very sensitive, the detection limit is 40nM, the results are as follows Figure 5 shown.

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Abstract

The invention discloses a ratiometric fluorescent probe for detecting hydrogen sulfide. The ratiometric fluorescent probe is formed by taking a coumarin fluorophore as a donor and a half-cyanine fluorophore as a receptor through piperazine connection and is used for detecting the hydrogen sulfide based on an FRET (Fluorescence Resonance Energy Transfer) mechanism. A chemical structural formula of the ratiometric fluorescent probe is as shown in formula (I). An experiment verifies that when no hydrogen sulfide exits, red fluorescent light of a half-cyanine part can be emitted by the ratiometric fluorescent probe as FRET is opened; when the hydrogen sulfide exists, a nucleophilic addition reaction is carried out by half-cyanine and the hydrogen sulfide, the FRET is restrained, blue fluorescent light of a coumarin part can be emitted by the ratiometric fluorescent probe, a ratio-metering type fluorescent response is realized, and the ratiometric fluorescent probe has the advantages that the operation is simple, the response is sensitive, and the like. The experiment indicates that the ratiometric fluorescent probe has a wide application prospect in detecting whether a hydrogen sulfide-containing sample is a biological cell containing exogenous hydrogen sulfide or endogenous hydrogen sulfide or in a solution containing the hydrogen sulfide or in mitochondria locating in a cell.

Description

technical field [0001] The invention relates to a hydrogen sulfide fluorescent probe, in particular to a ratio fluorescent probe for detecting hydrogen sulfide and its application; it belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Hydrogen sulfide (H 2 S) as a kind of endogenous gas sensing signal molecule, which acts as an antioxidant and a scavenger of reactive oxygen species. However, abnormal concentrations of hydrogen sulfide can cause many diseases, such as Alzheimer's disease, Down's syndrome and diabetes. Therefore, the quantitative detection of H2S in biological systems has attracted extensive attention. [0003] Fluorescence detection method has the characteristics of convenient operation, high sensitivity, strong selectivity, and can realize real-time and online detection of biological samples, and has attracted extensive attention. However, most of the reported hydrogen sulfide probes are fluorescent "off-on" t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D209/14G01N21/64C12Q1/02
Inventor 赵宝祥苗俊英冯笑张涛
Owner SHANDONG UNIV
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