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Oxathiacyclopentane-benzocoumarin compound, preparation method thereof and application of oxathiacyclopentane-benzocoumarin compound as fluorescent probe

A technology of oxathiolane and benzocoumarin, applied in the field of fluorescent probes, can solve the problems of complicated synthesis, small Stokes shift, easy to be affected by the environment, etc., and achieves a wide range of pH applications and good biocompatibility good optical properties

Active Publication Date: 2022-07-12
TIANSHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although a large number of fluorescent probes for the detection of HClO have been found, most of the fluorescent probes still have certain defects in practical applications, such as cumbersome synthesis, high cost, low fluorescence quantum yield, slow response time, poor water solubility, Stokes Small displacement, easy to be affected by the environment, low sensitivity, narrow pH application range, and some probes cannot be used for biological applications and visual imaging, etc.

Method used

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  • Oxathiacyclopentane-benzocoumarin compound, preparation method thereof and application of oxathiacyclopentane-benzocoumarin compound as fluorescent probe
  • Oxathiacyclopentane-benzocoumarin compound, preparation method thereof and application of oxathiacyclopentane-benzocoumarin compound as fluorescent probe
  • Oxathiacyclopentane-benzocoumarin compound, preparation method thereof and application of oxathiacyclopentane-benzocoumarin compound as fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0047] Synthesis of Intermediate BM: In a 50 mL round bottom flask, a mixture of 2-hydroxynaphthaleneacetaldehyde (1.72 g, 10 mmol) and ethyl acetoacetate (1.56 g, 12 mmol) was dissolved in 20 mL of ethanol. A catalytic amount of piperidine was added and the reaction mixture was stirred at room temperature for 20 minutes. It was further heated to reflux for 2 hours, after completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, and the resulting pale yellow solid product was filtered, dried and recrystallized from ethanol to obtain intermediate BM, yield 82%; melting point : 1 H NMR (400 Hz, CDCl 3 ) (attached figure 1 ):δ H (ppm): 9.331 (s, 1H), 8.369 (d, J=8.4Hz, 1H), 8.099 (d, J=9.2Hz, 1H), 7.924 (d, J=8.0 Hz, 1H), 7.757 (t , J=8.4Hz, 1H), 7.619(t, J=6.4Hz, 1H), 7.473(d, J=9.2 Hz, 1H), 2.790(s, 3H, CH 3 )ppm; 13 C NMR (101MHz, CDCl 3 ) (attached figure 1 )δ 195.55, 159.45, 156.20, 143.21, 136.31, 130.26, 129.90, 129.29, 1...

Embodiment 2

[0050] The solvent effect of the oxathiolane-benzocoumarin compound of the present invention (abbreviated as BMH in the present invention) as a fluorescent probe was investigated.

[0051] To investigate the effect of different solvent systems on ligand fluorescence, it was found that BMH plus equivalent hypochlorous acid in different solvents (ethanol, methanol, dichloromethane, ethyl acetate, dimethylformamide, dimethylmethylene The fluorescence intensity of sulfone, water, acetonitrile) is obviously different. The ligand BMH plus an equivalent amount of hypochlorous acid has strong fluorescence in water, and the fluorescence in other solvents is weak. Therefore, in the next experiment, choose PBS (10mM, PH= 7.4) The solution was used as the test system.

Embodiment 3

[0053] The selective and competitive study of the oxathiolane-benzocoumarin compound (BMH) of the present invention as a fluorescent probe.

[0054] In order to study the specific selectivity of probe BMH for HClO, as Figure 7 As shown, in the PBS (0.01M, PH=7.4) solution system, when various reactive oxygen species, amino acids, anions and cations are added, the probe BMH has almost no fluorescence change and no fluorescence is generated, only the probe BMH is generated after the addition of HClO. Strong fluorescence.

[0055] Subsequently, the competition of probe BMH to HClO under the condition of coexistence of other interfering substances was investigated. Probe BMH (10 μM) was added to PBS solution (2 mL) followed by various other analyte ions (Ag + , Fe 3+ ,Mg 2+ ,Pb 2+ ,Cu 2+ , Al 3+ ,Na + , Zn 2+ ,Ca 2+ ,Cr 3+ ,), anion (F - ,Cl - ,Br - ,I - ,SO 4 2- ,S 2 O 3 2- ,S 2- ,S 2 O 4 - ,HCO 3 - ,NO 3 - ,NO 2 - ), amino acids (Cys, Gin, Glu, Gly,...

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Abstract

The invention relates to the technical field of fluorescent probes, and discloses an oxathiacyclopentane-benzocoumarin compound, a preparation method thereof and application of the oxathiacyclopentane-benzocoumarin compound as a fluorescent probe. According to the oxathiolane-benzocoumarin compound, benzocoumarin serves as a fluorophore, and the compound serves as a fluorescent probe, has good optical properties, can specifically recognize HClO, and is short in response time, wide in pH application range, low in detection limit and good in water solubility. Besides, the probe BMH can be used as a solid probe to be applied to rapid detection of HClO, can also be used for detecting HClO in an actual water sample so as to obtain a satisfactory recovery rate, has good biocompatibility, and can be successfully applied to accurate monitoring of changes of levels of endogenous and exogenous HClO in natural HClO and living RAW 264.7 cells.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to an oxathiolane-benzocoumarin compound, a preparation method thereof, and use as a fluorescent probe. Background technique [0002] Reactive oxygen species (ROS) are important metabolites in physiological processes. As one of the important members of ROS, hypochlorous acid (HClO) has strong oxidative properties. Endogenous hypochlorous acid is produced by the reaction of hydrogen peroxide and chloride ions under the catalysis of heme myeloperoxidase (MPO). In the body's immune system, hypochlorous acid is a powerful weapon against invading pathogens. However, when the concentration of hypochlorous acid in the body is too high, oxidative stress and chlorination stress will occur, disrupt the normal metabolism of the body, damage tissues, and cause various diseases, such as neurodegenerative diseases, kidney disease, heart disease, and liver ischemia. Reperfusion injur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D411/04C09K11/06G01N21/64
CPCC07D411/04C09K11/06G01N21/6428G01N21/643G01N21/6486C09K2211/1088C09K2211/1092
Inventor 刘岿张建斌司长代王晓峰冯小强李晓芳
Owner TIANSHUI NORMAL UNIV
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