CN111072650B - Benzothiazole hydrogen sulfide fluorescent probe - Google Patents

Benzothiazole hydrogen sulfide fluorescent probe Download PDF

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CN111072650B
CN111072650B CN201811227297.XA CN201811227297A CN111072650B CN 111072650 B CN111072650 B CN 111072650B CN 201811227297 A CN201811227297 A CN 201811227297A CN 111072650 B CN111072650 B CN 111072650B
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hydrogen sulfide
fluorescent probe
benzothiazole
sulfide fluorescent
detecting hydrogen
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CN111072650A (en
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杨绍祥
田红玉
刘永国
陈海涛
孙宝国
王嘉琳
王皓
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Beijing Technology and Business University
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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Abstract

The invention discloses a benzothiazole fluorescent probe for detecting hydrogen sulfide, which has the following specific chemical structural formula:

Description

Benzothiazole hydrogen sulfide fluorescent probe
Technical Field
The invention relates to a benzothiazole hydrogen sulfide fluorescent probe and application thereof in detection of hydrogen sulfide.
Background
Hydrogen sulfide (H)2S) smells of rotten eggs at low concentrations. Inhalation of a small amount of high concentration hydrogen sulfide can be fatal in a short time, and is an acute virulent.
H2S is a third endogenous gas signaling molecule following NO, CO. It is produced by tissue sulfoether-beta-synthetase, sulfoether-gamma-lyase and 3-mercaptopropionate transferase, and is distributed in various tissues and organs. H2S is involved in most physiological processes in the body as an immunomodulator, neurotransmitter. However, H2Abnormalities in S content also lead to the development of many diseases, tumors, diabetes, stroke, alzheimer' S disease, etc. In addition, the wine drunk by people in daily life has H in the fermentation process2S production, excess H2S can affect the taste of the wine, and even the health of a human body can be affected by excessive intake.
The organic small molecule fluorescent probe detection method is a very effective detection method due to the advantages of simple and convenient operation, rapid detection, high sensitivity, potential imaging and the like, and a plurality of organic small molecule fluorescent probes are developed at present. Therefore, the fluorescent probe is used as a detection tool to measure the content of the hydrogen sulfide, and the method has important significance for food quality and safety research.
Disclosure of Invention
The invention aims to provide a fluorescent probe for detecting hydrogen sulfide, which is suitable for detecting hydrogen sulfide in products such as food, medicines, cosmetics and the like.
More particularly, the present invention relates to a fluorescent probe for detecting hydrogen sulfide, which is represented by the following formula:
Figure BSA0000172347390000011
drawings
FIG. 1 shows the change in fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) in phosphate buffered saline (pH 7.4) with the addition of hydrogen sulfide at various concentrations. Embedding a graph: the concentration of hydrogen sulfide.
FIG. 2 is a standard curve of fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) as a function of hydrogen sulfide concentration in phosphate buffered saline (pH 7.4).
FIG. 3 shows the color change of the solution after the fluorescent probe (10. mu.M) of the present invention reacts with hydrogen sulfide (100, 200, 300, 400, 500, 600. mu.M) at different concentrations under natural light.
Detailed Description
Example 1 preparation of fluorescent Probe for detecting Hydrogen sulfide
The synthetic route is shown as the following formula:
Figure BSA0000172347390000021
20mL of ethanol dissolved 6-hydroxynaphthaldehyde (0.86g, 5mmol) and 4-aminothiophenol (0.63g, 5mmol) in a round-bottomed flask. Stir at room temperature for 10min and slowly add toluene sulfonic acid (0.17g, 1mmol) to the round bottom flask while adding additional 10mL ethanol and continue stirring with heating to reflux for 5 h. Stopping heating, cooling to room temperature, adding 50mL of distilled water, stirring and mixing, standing for 15min, filtering and drying to obtain a yellow solid, namely the compound 3(1.29g, 93.5%), and directly carrying out the next step according to the steps without purification.
Dissolving the compound 3(0.5g, 1.8mmol) with 20mL of trichloromethane, stirring, adding 2-thiophenecarbonyl chloride (0.29g, 1.8mmol) and a catalytic amount of triethylamine, adding 10mL of trichloromethane into a round-bottom flask, and heating and refluxing for 4h to obtain a colorless and transparent reaction solution. After the reaction was completed, heating was stopped, the reaction mixture was cooled to room temperature, the solvent was removed by rotary evaporation, and the mixture was purified by column chromatography (petroleum ether: ethyl acetate 4: 1) to obtain a white solid, which was the target product (0.570g, 81.8%).
The product is characterized by nuclear magnetic hydrogen spectrum and nuclear magnetic carbon spectrum.
1H NMR(300MHz，DMSO)，δ(ppm)：8.78(s，1H)，8.28(d，J＝4.35Hz，2H)，8.20(d，J＝3.96Hz，1H)，8.12-8.14(m，4H)，8.11(d，J＝Hz，1H)，7.96(s，1H)，7.58(t，J＝4.41Hz，2H)，7.50(t，J＝3.78Hz，1H)，7.35(s，1H).13C NMR(75MHz，DMSO)：δ(ppm)：168，161，154，150，136，135，132，131，130，129，128，127，126，125，123，120.
The change of the fluorescence intensity of the fluorescent probe of the invention along with the hydrogen sulfide is shown in figure 1, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) along with the change of the hydrogen sulfide concentration can be made according to the change, the standard curve is shown in figure 2, and the fluorescent probe of the invention can be used for quantitative detection of the hydrogen sulfide through establishment of the standard curve. The color change of the solution after the fluorescent probe reacts with hydrogen sulfide with different concentrations is shown in figure 3, the solution of the fluorescent probe gradually changes from colorless to yellow along with the increase of the concentration of the hydrogen sulfide, and the fluorescent probe can be used for qualitative and semi-quantitative detection of the hydrogen sulfide.

Claims (1)

1. A benzothiazole fluorescent probe for detecting hydrogen sulfide has a specific chemical structural formula as follows:
Figure FSA0000172347380000011
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103923640A (en) * 2014-04-30 2014-07-16 大连理工常熟研究院有限公司 Benzothiazoles fluorescent probe for identifying hydrogen sulfide and application of fluorescent probe
CN104531136A (en) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe
CN105419788A (en) * 2015-12-25 2016-03-23 济南大学 Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103923640A (en) * 2014-04-30 2014-07-16 大连理工常熟研究院有限公司 Benzothiazoles fluorescent probe for identifying hydrogen sulfide and application of fluorescent probe
CN104531136A (en) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe
CN105419788A (en) * 2015-12-25 2016-03-23 济南大学 Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Design, synthesis and evaluation of a novel fluorescent probe to accurately detect H2S in lysosomes;Lujuan Liao，等;《Tetrahedron Letters》;20180530;第59卷;全文 *

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