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Ratiometric fluorescent probe for detecting sulfur dioxide derivatives and application thereof

A ratiometric fluorescent probe, sulfur dioxide technology, applied in fluorescence/phosphorescence, organic chemistry, luminescent materials, etc., to achieve a targeted effect

Inactive Publication Date: 2020-07-03
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The search found that the energy donor 3-(pyridin-4-yl)-6-(N,N-diethyl)-coumarin fluorophore, the energy acceptor (E)-2-(3-cyano-4 -(4-(disubstituted amino)styryl)-5,5-dimethylfuran-2(5H)-ylidene)malononitrile and linker acetylpiperazine based on fluorescence resonance energy transfer mechanism A ratiometric fluorescent probe for the detection of sulfur dioxide derivatives has not been reported

Method used

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  • Ratiometric fluorescent probe for detecting sulfur dioxide derivatives and application thereof
  • Ratiometric fluorescent probe for detecting sulfur dioxide derivatives and application thereof
  • Ratiometric fluorescent probe for detecting sulfur dioxide derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (E)-2-(3-cyano-5,5-dimethyl-4-(4-(piperazine-1-)styrene)furan-2(5H)-ylidene)malononitrile ( 10mmol, 3.73g) was dissolved in dry dichloromethane (30mL), dry triethylamine (12mmol, 1.22g) was added, then chloroacetyl chloride (12mmol, 1.34g) was added dropwise under ice-bath conditions, and the reaction The time is 1h. After the reaction, the mixture was washed 5 times with saturated sodium bicarbonate solution (300 mL), and the organic phase was dried for 2 h by adding an appropriate amount of anhydrous sodium sulfate. After filtration and concentration, Intermediate 1 was obtained by column chromatography.

[0028] 3-(Pyridin-4-yl)-6-(N,N-diethyl)-coumarin (10.5mmol, 147.57mg) and intermediate 1 (0.5mmol, 224.5mg) were dissolved in acetonitrile (10mL) , Potassium iodide (0.6mmol, 99.6mg) was added, and the reaction time of reflux was about 16h. After the temperature was cooled to room temperature, precipitation occurred.

[0029] The obtained precipitate is the ratiom...

Embodiment 2

[0034] In a 10mL volumetric flask, prepare a ratio fluorescent probe with a concentration of 5 μM for detecting sulfur dioxide derivatives according to the present invention, and add 10 equivalents of ions and biological thiols, or 1 equivalent of SO 3 2- / HSO 3 - , Fluorescence test was performed after 15 minutes of action.

[0035] The results show that the probe of the present invention is only for SO 3 2- / HSO 3 - have better responsiveness and selectivity, see figure 1 .

Embodiment 3

[0037] In a 10mL volumetric flask, prepare a ratio fluorescent probe whose concentration is 5 μM to detect sulfur dioxide derivatives according to the present invention, and add different equivalents of SO with a micro-injector. 3 2- , Fluorescence test was performed after 15 minutes of action.

[0038] The results showed that the ratio of the fluorescence intensity at 568nm to the fluorescence intensity at 648nm relative to SO 3 2- The concentration has a linear relationship within a certain range, see figure 2 .

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Abstract

The invention discloses a ratiometric fluorescent probe for detecting sulfur dioxide derivatives. The ratiometric fluorescent probe is composed of an energy donor 3-(pyridine-4-yl)-6-(N,N-diethyl)-coumarin, an energy receptor (E)-2-(3-cyano-4-(4-(disubstituted amino)styryl)-5,5-dimethylfuran-2(5H)-subunit) malononitrile and a linking group acetyl piperazine. The chemical structure is shown as a formula (I). The probe can selectively detect HSO3<-> / SO3<2->, and along with the increase of the concentration of HSO3<-> / SO3<2->, the fluorescence emission intensity of the probe is gradually enhancedat 568nm and is gradually weakened at 648nm; and the ratio (I568 / I648) of the two fluorescence emission peaks and the concentration of HSO3<-> / SO3<2-> have a linear relationship within a certain range. Besides, the probe has a mitochondrial targeting property, can detect endogenous and exogenous HSO3<-> / SO3<2-> of cells, and has considerable application prospects in the fields of industrial detection and biological detection.

Description

technical field [0001] The invention relates to a ratio fluorescent probe and its application, in particular to a ratio fluorescent probe for detecting sulfur dioxide derivatives based on a fluorescence resonance energy transfer mechanism and its application; it belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Biological endogenous sulfur dioxide derivatives are usually produced by the hydrogen sulfide oxidation process in the cytoplasm and mitochondria or the enzymatic reaction of sulfur-containing amino acids, and it is a very important biogas signal molecule. Sulfur dioxide derivatives in organisms as HSO 3 - / SO 3 2- Existing in the form of human body, it can participate in many important physiological activities such as blood pressure regulation and metabolism. On the other hand, excessive inhalation of sulfur dioxide derivatives by the human body can cause adverse physiological reactions such as respiratory diseases a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
CPCC07D405/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/6428G01N21/6456
Inventor 赵宝祥孙琬雪苗俊英李娜
Owner SHANDONG UNIV
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