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Specific fluorescent probe for identifying hydrogen sulfide and application of probe

A fluorescent probe, hydrogen sulfide technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems such as damage to the sample to be tested, inability to achieve sulfide detection, achieve good fluorescence emission spectral characteristics, and simple synthesis process Easy, highly sensitive effect

Active Publication Date: 2014-05-21
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

[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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  • Specific fluorescent probe for identifying hydrogen sulfide and application of probe
  • Specific fluorescent probe for identifying hydrogen sulfide and application of probe
  • Specific fluorescent probe for identifying hydrogen sulfide and application of probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 The chemical synthesis of 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one

[0028] Figure 10 Shown in 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one synthetic route, its synthetic steps are as follows:

[0029] (1) Dissolve 0.5 mmol of resorufin sodium salt, 0.625 mmol of potassium carbonate, and 0.5 mmol of 2,4-dinitrobromobenzene in 10 mL of N,N-dimethylformamide, and react at 80 °C for 4 h;

[0030] (2) Pour the reaction solution into ice water, a large amount of solid precipitates, and filter;

[0031] (3) The solid was purified by silica gel chromatography, and eluted with ethyl acetate-n-hexane (1: 1 v / v), to obtain 159.6 mg of orange solid powder;

Embodiment 2

[0032] Example 2 The selectivity of 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one for different substances

[0033] (1) Prepare 99 μl metabolic reaction system in advance, including PBS buffer (10 mM) at pH 7.4: ethanol (volume ratio 9:1), fluoride ion (100 μM), chloride ion (50 μM), bromide ion (100 μM), L-iodide ion (100μM), sodium ion (100μM), potassium ion (100μM), calcium ion (100μM), magnesium ion (100μM), nitrate ion (100μM), sodium hydrosulfide (100μM)

[0034] (2) Add 1 μl of 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0035] (3) After 60 min, perform fluorescence detection (λ Ex =550 nm, λ Em =590 nm); calculate the fluorescence intensity in each system (see Image 6 );

Embodiment 3

[0036] Example 3 Linear relationship between 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one and hydrogen sulfide concentration

[0037] (1) Prepare 99 μl metabolic reaction system in advance, including PBS buffer (10 mM) at pH 7.4: ethanol (volume ratio 9:1), sodium hydrosulfide (0-200 μM), react at 37°C for 30 minutes ;

[0038] (2) Add 1 μl of 7-(2,4-dinitrophenoxy)-3H-phenoxazin-3-one at a final concentration of 10 μM to the reaction system to initiate the reaction;

[0039] (3) After 60 min, perform fluorescence detection (λ Ex =550 nm, λ Em =590 nm); calculate the fluorescence intensity in each system, establish the standard curve of fluorescence intensity and hydrogen sulfide concentration, the standard curve is y = 243.72x - 2422.7, where, y represents the fluorescence intensity, x represents the concentration of hydrogen sulfide (see Figure 7 );

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Abstract

The invention relates to a specific fluorescent probe for identifying hydrogen sulfide and an application of the probe, belonging to the field of fine chemical engineering. The fluorescent probe is a resorufin derivative. Resorufin sodium salt, potassium carbonate and 2, 4-binitro bromobenzene are mixed in proportion in acetonitrile liquor to be heated, and finally are purified by silica gel chromatography to obtain the fluorescent probe. The fluorescent probe and a corresponding hydrogen sulfide content detection process are not interfered by matrixes and impurities in a biosystem and can be used for quantitative determination of hydrogen sulfide content in various biosystems. The fluorescent probe has high specificity and can be hydrolyzed with hydrogen sulfide after being specifically cyclized to obtain a hydrolysate with broken ether bonds. The probe is low in cost and feasible, can be obtained by chemical synthesis and is simple and feasible in synthetic process. The probe is high in sensitivity, and has good fluorescence emission spectrum characteristics (600-650nm). In the wavelength range, the background fluorescence of a biological sample is weak, so that the probe is suitable for detecting hydrogen sulfide content in cells. Hydrogen sulfide is quantitively detected by drawing a standard curve.

Description

technical field [0001] The invention relates to a specific fluorescent probe for identifying hydrogen sulfide and its application, belonging to the field of fine chemical industry. Background technique [0002] Type background description paragraph here 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 physiologica...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D265/38G01N21/64
Inventor 崔京南冯磊
Owner CHANGSHU RES INST OF DALIAN UNIV OF TECH CO LTD
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