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Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe

A fluorescent probe and fluoride ion technology, applied in the field of specific fluorescent probes, can solve problems such as inconclusive fluoride ion concentration, and achieve the effect of simple and easy synthesis process and high sensitivity

Active Publication Date: 2015-03-25
苏州新启材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the concentration of fluoride ion that can exert an anti-caries effect is still inconclusive

Method used

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  • Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe
  • Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe
  • Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Chemical synthesis of 2-(2-triisopropylsiloxyphenyl)benzothiazole

[0022] (1) Dissolve 0.5 mmol of 2-(2-hydroxyphenyl) benzothiazole and 0.625 mmol of triethylamine in 10 mL of tetrahydrofuran, dropwise add 5 mL of tetrahydrofuran containing 0.6 mmol of acetyl chloride under ice bath conditions, and stir for 8 h ;

[0023] (2) the reaction solution is distilled under reduced pressure to obtain a white solid residue;

[0024] (3) The solid was purified by silica gel chromatography and eluted with ethyl acetate-n-hexane (1:3 v / v) to obtain 116 mg of white solid powder. 1 H NMR (400MHz, CDCl 3 )δ8.39–8.27(m, 1H), 8.00(d, J=8.1Hz, 1H), 7.79(t, J=10.4Hz, 1H), 7.35(t, J=7.6Hz, 1H), 7.21( dt, J=9.2, 4.5Hz, 2H), 6.96 (t, J=7.5Hz, 1H), 6.87 (d, J=8.2Hz, 1H), 1.40 (td, J=15.0, 7.5Hz, 3H), 1.10–1.00 (m, 18H).

Embodiment 2

[0025] Example 2 Selectivity of 2-(2-triisopropylsiloxyphenyl)benzothiazole to different substances

[0026] (1) Prepare 99 μL of metabolic reaction system in advance, including acetonitrile, fluoride ion (100 μM), chloride ion (100 μM), bromide ion (100 μM), iodide ion (100 μM), nitrate ion (100 μM), sulfate ion (100 μM) , carbonate ions (100 μM);

[0027] (2) Add 1 μL of 2-(2-triisopropylsiloxyphenyl)benzothiazole with a final concentration of 10 μM to the reaction system to initiate the reaction;

[0028] (3) After 60min, perform fluorescence detection and calculate the fluorescence intensity in each system (see figure 1 ).

Embodiment 3

[0029] Example 3 Relationship between 2-(2-triisopropylsiloxyphenyl)benzothiazole and fluoride ion concentration

[0030] (1) Prepare 99 μL of metabolic reaction system in advance, including acetonitrile and fluoride ion (0-20 μM), and react at 25°C for 30 minutes;

[0031] (2) Add 1 μL of 2-(2-triisopropylsiloxyphenyl)benzothiazole with a final concentration of 10 μM to the reaction system to initiate the reaction;

[0032] (3) After 60 minutes, fluorescence detection was performed, and the fluorescence intensity in each system was calculated. (See figure 2 );

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Abstract

The invention discloses a specific fluorescent probe for recognizing fluorine ions and an application of the specific fluorescent probe, and belongs to the field of fine chemistry. The fluorescent probe is a 2-(2-hydroxycyclohexyl phenyl ketone) benzothiazole derivative. The 2-(2-hydroxycyclohexyl phenyl ketone) benzothiazole derivative and triethylamine are dissolved in tetrahydrofuran, acyl chloride is slowly dripped into the tetrahydrofuran in ice bath, and finally, purification is realized by silica gel chromatography to obtain the fluorescent probe. The fluorescent probe and a corresponding fluorine ion content detection process cannot be interfered by a biological system matrix and impurities, and can be used for quantitatively measuring fluorine ion content in various biological systems. The fluorescent probe has high specificity, can specifically realize silicon-oxygen bond breakage under the action of fluorine ions, is cheap and available, high in sensitivity and suitable for detecting the fluorine ion content in cells and can be obtained by chemical synthesis, the synthesis process is simple and practicable, and the fluorine ions are quantitatively measured by drawing a standard curve.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and relates to a specific fluorescent probe for identifying fluoride ions and its application. Background technique [0002] Fluoride is one of the essential trace elements for the human body, and in some countries, fluoride is added to drinking water and toothpaste to prevent dental caries. However, there is still no conclusion about the fluoride ion concentration that can play an anti-caries effect. my country's drinking water hygiene standard GB5749-2006 stipulates that fluoride in drinking water is less than or equal to 1.0mg / L, which can play a role in preventing caries; the American ADA organization believes that the effective fluoride content in bottled water should be 0.6 ~ 1.2mg / L. However, excessive intake of fluoride can lead to both acute and chronic diseases. Among them, acute diseases include gastrointestinal and renal dysfunction, etc., and chronic diseases include dental flu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/18G01N21/64
Inventor 冯磊崔京南
Owner 苏州新启材料科技有限公司
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