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Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe

A fluorescent probe, thiophenol technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of thiophenol toxicity, hindlimb paralysis, muscle weakness, etc., and achieve the effect of rapid response

Active Publication Date: 2015-04-22
CHANGSHU RES INST OF DALIAN UNIV OF TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, thiophenol is extremely toxic, and its half-lethal concentration to fish is 0.01mM-0.4mM. Human body exposure to thiophenol liquid or gas will cause serious damage to the central nervous system and other related systems. Includes shortness of breath, muscle weakness, hind limb paralysis, coma and even death

Method used

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  • Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe
  • Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe
  • Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 The chemical synthesis of 2-benzothiazolyl-6-(2,4-dinitrophenoxy)naphthalene

[0021] (1) 0.5mmol of 2-benzothiazolyl-6-naphthol and 0.625mmol of potassium carbonate and 0.6mmol of 2,4-dinitrobromobenzene were dissolved in 10mL of N,N dimethylformamide, 80 ℃ for 12 hours;

[0022] (2) The reaction solution is distilled under reduced pressure to obtain a light yellow solid residue;

[0023] (3) The solid was purified by silica gel chromatography and eluted with ethyl acetate-n-hexane (1:3 v / v) to obtain 188 mg of light yellow solid powder. 1 H NMR (400MHz, DMSO) δ8.96(d, J=2.2Hz, 1H), 8.81(s, 1H), 8.48(dd, J=9.2, 2.3Hz, 1H), 8.37(d, J=8.9Hz ,1H), 8.30(d,J=8.5Hz,1H), 8.21(d,J=8.0Hz,1H), 8.11(d,J=7.5Hz,2H), 7.89(s,1H), 7.59(t , J=7.6Hz, 2H), 7.51(t, J=7.4Hz, 1H), 7.37(d, J=9.2Hz, 1H).

Embodiment 2

[0024] Example 2 The selectivity of 2-benzothiazolyl-6-(2,4-dinitrophenoxy)naphthalene to different substances

[0025] (1) Prepare 99 μL metabolic reaction system in advance, including PBS buffer (10 mM) at pH 7.4: DMF (volume ratio 1:1), mercaptoethanol (100 μM), p-nitrothiophenol (100 μM), cysteine (100μM), homocysteine ​​(100μM), glutathione (100μM), sodium hydrosulfide (100μM), thiophenol (100μM);

[0026] (2) Add 1 μL of 2-benzothiazolyl-6-(2,4-dinitrophenoxy)naphthalene at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0027] (3) After 20min, carry out fluorescence detection, calculate the fluorescence intensity in each system (see figure 1 ).

Embodiment 3

[0028] Example 3 Linear relationship between the concentration of 2-benzothiazolyl-6-(2,4-dinitrophenoxy)naphthalene and thiophenol

[0029] (1) Prepare 99 μL of metabolic reaction system in advance, including PBS buffer (10 mM) at pH 7.4: DMSO (volume ratio 1:9), thiophenol (0-200 μM), and react at 25°C for 30 minutes;

[0030] (2) Add 1 μL of 2-benzothiazolyl-6-(2,4-dinitrophenoxy)naphthalene at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0031] (3) After 20 min, perform fluorescence detection, and calculate the fluorescence intensity in each system. (See figure 2 ).

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Abstract

The invention discloses a specific fluorescence probe for identifying thiophenol and application of the specific fluorescence probe and belongs to the field of fine chemical industry. The specific fluorescence probe is a derivative of 2-benzothiazole-6-naphthol and is prepared by the following steps: mixing the 2-benzothiazole-6-naphthol and 2, 4-dinitrobenzene into an N, N-dimethylformamide solution according to a proportion, heating, and finally, purifying by adopting silica gel chromatography to obtain the fluorescence probe. The fluorescence probe and a corresponding thiophenol content detecting process can not be interfered by matrixes and impurities in a biological system and can be used for quantitatively determining the thiophenol content in various biological systems. The specific fluorescence probe is high in specificity, can be hydrolyzed after being acted with the thiophenol, namely an ether bond is fractured; is cheap and is easy in acquisition, can be obtained by chemical synthesis, is simple and feasible in synthetic process; is high in sensitivity, is good in fluorescence attribute. A hydrolysate can be excited by a two-photon laser with 800nm as an excitation light source, a biological sample is weak in background fluorescence, and the specific fluorescence probe is suitable for detecting the thiophenol content in cells and is capable of quantitatively determining the thiophenol 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 thiophenol and its application. Background technique [0002] In the fields of chemistry, biology, and environmental science, it is particularly important to develop high-sensitivity and high-selectivity detection techniques for related biologically active or toxic molecules. Thiophenol belongs to thiol compounds and is widely used in the preparation of pesticides, medicines and various industrial products, and is an important chemical raw material. However, thiophenol is extremely toxic, and its half-lethal concentration to fish is 0.01mM-0.4mM. Human body exposure to thiophenol liquid or gas will cause serious damage to the central nervous system and other related systems. These include shortness of breath, muscle weakness, hind limb paralysis, coma and even death. Therefore, considering the harm of thiophenol to the environment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D277/66G01N21/64
Inventor 冯磊崔京南
Owner CHANGSHU RES INST OF DALIAN UNIV OF TECH CO LTD
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