A kind of fluorescent probe and its application of benzothiazole recognition hydrogen sulfide

A technology of benzothiazoles and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of sample damage and failure to detect sulfides, achieve good fluorescence emission spectrum characteristics, simple synthesis process, and high sensitivity Effect

Active Publication Date: 2016-05-25
CHANGSHU RES INST OF DALIAN UNIV OF TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Traditional methods for the detection of hydrogen sulfide, including colorimetric assays, polarographic sensing methods, and gas chromatography, usually cause damage to the sample to be tested, or cannot detect sulfide in organisms at all.

Method used

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  • A kind of fluorescent probe and its application of benzothiazole recognition hydrogen sulfide
  • A kind of fluorescent probe and its application of benzothiazole recognition hydrogen sulfide
  • A kind of fluorescent probe and its application of benzothiazole recognition hydrogen sulfide

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Experimental program
Comparison scheme
Effect test

Embodiment 12-（2

[0024] Chemical synthesis of embodiment 12-(2(2,4-dinitrophenoxy))benzothiazole

[0025]

[0026] (1) Dissolve 0.5mmol of 2-(2-hydroxyphenyl)benzothiazole, 0.625mmol of potassium carbonate and 0.5mmol of 2,4-dinitrobromobenzene in 10mL of acetonitrile, and react at 80°C for 4h;

[0027] (2) The reaction solution is subjected to vacuum distillation;

[0028] (3) The solid was purified by silica gel chromatography, and eluted with ethyl acetate-n-hexane (1:3v / v) to obtain a light yellow solid. For the characterization results, see figure 1 , figure 2 and image 3 . 1 HNMR(400MHz,DMSO)δ8.98(d,J=2.8Hz,1H),8.50(dd,J=7.9,1.6Hz,1H),8.42(dd,J=9.3,2.8Hz,1H),8.11( d,J=8.0Hz,1H),8.04(d,J=8.1Hz,1H),7.79–7.68(m,1H),7.66–7.51(m,2H),7.47(dd,J=14.4,7.5Hz ,2H),7.24(d,J=9.3Hz,1H).13CNMR(100MHz,CDCl3)δ160.87,155.66,152.67,150.68,141.78,139.54,135.50,132.51,131.30,128.99,127.45,126.657,125. 123.46, 122.25, 122.13, 121.52, 117.80. HRMScalcdforC16H14NO5+([M+H]+)394.0492,found394.0501.

Embodiment 22-（2

[0029] Example 22-(2(2,4-dinitrophenoxy))benzothiazole selectivity for different substances

[0030] (1) Prepare 99 μl metabolic reaction system in advance, including PBS buffer (10 mM) at pH 7.4: dimethyl sulfoxide (volume ratio 7:3), fluoride ion (100 μM), chloride ion (50 μM), bromide ion ( 100μM), iodide ion (100μM), sodium ion (100μM), potassium ion (100μM), calcium ion (100μM), magnesium ion (100μM), nitrate ion (100μM), sodium hydrosulfide (100μM);

[0031] (2) Add 1 μl of 2-(2(2,4-dinitrophenoxy))benzothiazole at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0032] (3) After 30 minutes, perform fluorescence detection (λ Ex =300nm, λ Em =458nm); calculate the fluorescence intensity in each system (see Figure 4 ).

Embodiment 32-（2

[0033] Example 32-(2(2,4-dinitrophenoxy))benzothiazole and hydrogen sulfide concentration linear relationship

[0034] (1) Prepare 99μl metabolic reaction system in advance, including PBS buffer (10mM) at pH 7.4: dimethyl sulfoxide (volume ratio 7:3), hydrogen sulfide (0-100μM), react at 37°C for 30 minute;

[0035] (2) Add 1 μl of 2-(2(2,4-dinitrophenoxy))benzothiazole at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0036] (3) After 30 minutes, perform fluorescence detection (λ Ex=300nm, λ Em =458nm); calculate the fluorescence intensity in each system, and establish the standard curve of fluorescence intensity and hydrogen sulfide concentration (see Figure 5 ); the standard curve is y=3695.9x-373.09, R2=0.9931, where y represents the fluorescence intensity at 458nm, and x represents the concentration of sodium hydrosulfide (the linear relationship between the concentration of hydrazine between 0uM and 100uM is satisfied).

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Abstract

The invention relates to a benzothiazoles fluorescent probe for identifying hydrogen sulfide, and the application of the fluorescent probe, belonging to the field of fine chemical industry. The fluorescent probe is 2-(2-hydroxy phenyl) benzothiazole derivatives, and is prepared by the steps of mixing 2-(2-hydroxy phenyl) benzothiazole with potassium carbonate and 2, 4-dinitro bromobenzene in proportion, and finally purifying by a silica gel column chromatography. The fluorescent probe and the corresponding hydrogen sulfide content detection process are not interfered by biological system matrix and impurities and can be used for quantitative measurement of hydrogen sulfide content in various biological systems. The benzothiazoles fluorescent probe is high in specificity, can be hydrolyzed after being specifically cyclized with the hydrogen sulfide, and namely, is hydrolysate of ether cleavage; the benzothiazoles fluorescent probe is cheap and easily available, can be obtained by chemical synthesis, and is simple and practicable in synthetic process; the benzothiazoles fluorescent probe is high in sensitivity, has good fluorescence emission spectrum characteristic (450-500nm), and can be used for quantitative measurement of the hydrogen sulfide by drawing a standard curve.

Description

technical field [0001] The invention relates to a fluorescent probe for recognizing hydrogen sulfide by benzothiazoles and an application thereof, belonging to the field of fine chemical industry. Background technique [0002] For centuries, hydrogen sulfide (H 2 S) is considered to be a toxic substance produced by geological activities or microbial action. This colorless, flammable gas has a disgusting smell of rotten eggs and is a strong irritant to the eyes and respiratory system of mammals. Excessive inhalation of hydrogen sulfide gas can lead to loss of consciousness, respiratory failure, cardiac arrest and other physiological reactions, and excessive absorption can lead to death. On the other hand, more and more studies have begun to challenge this traditional concept: mammals themselves can produce hydrogen sulfide under controlled conditions, and it is believed that oxygen sulfide plays an important role in maintaining normal physiological functions. Hydrogen sulf...

Claims

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Application Information

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