Lysosome target fluorescent probe of sulfur dioxide/sulfurous acid (hydrogen) saline

A fluorescent probe, sulfur dioxide technology, applied in the field of sulfur dioxide fluorescent probes, can solve the problems of fluorescent probes such as long response time and scattering interference, and achieve the effects of fast recognition speed, good specificity and high yield

Inactive Publication Date: 2018-05-15
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, molecular fluorescent probes for the detection of sulfur dioxide have been reported in the literature, but these common fluorescent probes have defects such as long response time and scattering interference, which may affect the application of sulfur dioxide detection in complex physiological environments

Method used

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  • Lysosome target fluorescent probe of sulfur dioxide/sulfurous acid (hydrogen) saline
  • Lysosome target fluorescent probe of sulfur dioxide/sulfurous acid (hydrogen) saline
  • Lysosome target fluorescent probe of sulfur dioxide/sulfurous acid (hydrogen) saline

Examples

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Embodiment 1

[0036] Example 1 Synthesis of a lysosome-targeted fluorescent probe for rapid detection of sulfur dioxide

[0037] (1) Synthesis of Compound 1

[0038] ;

[0039] In a 100 mL round bottom flask, the compound N-(2-aminoethyl)morpholine (1.30 g, 10 mmol) was added and mixed with 1,8-4-bromonaphthalic anhydride (2.77 g, 10 mmol), Add 30 mL of ethanol to it and stir under reflux, cool to room temperature, place the reaction system in a -5 °C environment, a large amount of solids precipitate, filter under reduced pressure, wash the filter cake with ethanol 2-3 times, and dry in vacuo to obtain compound 1 . The crude product was recrystallized from ethanol to obtain pure product. Yield: 88%.

[0040] (2) Synthesis of compound 2

[0041] ;

[0042] In a 100 mL round bottom flask, add 30 mL of ethanol, add compound 1 (1.945 g, 5 mmol), 80% hydrazine hydrate (1.00 g, 25 mmol), heat and reflux for 2-3 h, then cool to Filter under reduced pressure at room temperature, wash the...

Embodiment 2

[0046] Example 2 Compound Na-SO 2 -Lyso detects the fluorescence intensity of different concentrations of sodium bisulfite.

[0047] Preparation concentration is the fluorescent probe Na-SO obtained in embodiment 1 of 1 mM 2 -Lyso's acetonitrile test stock solution ready for use.

[0048]The final concentration of the probe was 10 μM, and PBS solution (pH 5.5) containing 5% acetonitrile solution was mixed with different concentrations of sodium bisulfite (1 μM, 3 μM, 6 μM, 10 μM, 15 μM, 21 μM, 27 μM, 34 μM, 42 μM, 51μM, 61μM, 72μM, 84μM, 97μM, 110μM, 121μM, 132μM, 143μM, 154μM, 170μM, 186μM, 200μM, 215μM, 230μM, 240μM, 250μM, 260μM) full effect, for fluorescence detection (λ ex =440 nm, λ em =545 nm). The fluorescence intensity in each system was obtained, and the standard curve of fluorescence intensity and sodium bisulfite concentration was established, and the results were as follows: figure 2 shown. Depend on figure 2 It can be seen that as the concentration of so...

Embodiment 3

[0049] Example 3 Compound Na-SO 2 - Kinetic test of Lyso in PBS buffer.

[0050] Preparation concentration is the fluorescent probe Na-SO obtained in embodiment 1 of 1 mM 2 -Lyso's acetonitrile test stock solution ready for use.

[0051] Prepare the probe with a final concentration of 10 μM, PBS solution (pH 5.5) containing 5% acetonitrile solution, fully react with sodium bisulfite (250 μM), and perform fluorescence detection every three seconds (λ ex =440 nm, λ em =545 nm). The fluorescence intensity in each system was obtained, and the standard curve of fluorescence intensity and time was established, such as image 3 shown. Depend on image 3 It can be seen that with the increase of time, the fluorescence intensity at 545 nm increases gradually, and the reaction reaches equilibrium within 9 s.

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Abstract

The invention provides a lysosome target fluorescent probe of sulfur dioxide/sulfurous acid (hydrogen) saline which can be used for qualitatively or quantitatively detecting the content of sulfur dioxide or derivatives in solutions, tissues or zebra fishes. The lysosome target fluorescent probe of sulfur dioxide is simple in synthesis step, raw materials are easy to obtain, the yield is high, andthe lysosome target fluorescent probe of sulfur dioxide is suitable for industrialized application; and meanwhile, the identification speed is high, interferences of various kinds of ions, amino acidand reactive oxygen can be resisted, and the lysosome target fluorescent probe of sulfur dioxide has the relatively good specificity, can be used for detecting variation of sulfur dioxide in cells andzebra fishes, and has potential application value for research of biological pathology and relevant diseases.

Description

technical field [0001] The invention relates to a sulfur dioxide fluorescent probe, which belongs to the field of small organic molecule fluorescent probes. Background technique [0002] Sulfur dioxide (SO 2 ) is one of the main pollutants in the atmosphere. After entering the respiratory tract, because it is easily soluble in water, most of them are blocked in the upper respiratory tract, and corrosive sulfurous acid, sulfuric acid and sulfate are formed on the moist mucous membrane, making the The stimulating effect is enhanced. Because of the antiseptic and antioxidative effects of sodium sulfite and sodium bisulfite, they are widely used as food additives, so SO 2 It is very closely related to human health. Furthermore, SO 2 Considered as the "fourth gas signal molecule", its concentration in organisms is closely related to its function, therefore, the design and synthesis of lysosome-targeted SO 2 Fluorescent probes are of great significance for studying their func...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029C09K2211/1033G01N21/6456G01N21/6486
Inventor 林伟英赵玉萍马燕燕
Owner UNIV OF JINAN
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