Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof

A technology of fluorescent probes and biothiols, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex synthesis process, low sensitivity, long response time, etc., and achieve high detection sensitivity and selectivity High and simple preparation method

Inactive Publication Date: 2019-08-16
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many of them have long response time, low sensitivity, c

Method used

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  • Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof
  • Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof
  • Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof

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Experimental program
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Example Embodiment

[0028] Example 1: Preparation of Compound 1:

[0029] N-diethylaminophenol (1.8 g, 10.9 mmol) and phthalic anhydride (1.8 g, 12.2 mmol) were reacted in 200 mL of benzene at 130 °C for 12 hours to obtain a white solid by suction filtration, and then the white solid (0.626 g , 2 mmol) was added to 10 mL of methanesulfonic acid containing p-hydroxyacetophenone (0.272 g, 2 mmol), reacted at 90 °C for 8 hours, added to 200 mL of ice water after cooling, added 10 mL of perchloric acid, and diluted with dichloride. Extraction with methane (50 mL × 3), drying and rotary evaporation of the solvent, and separation by column chromatography with a mixed solvent of dichloromethane and glacial acetic acid to obtain compound 1, yield: 33%. Synthetic routes such as figure 1 shown.

Example Embodiment

[0030] Example 2: Preparation of the fluorescent probe for detecting biological thiols in a water-soluble environment according to the present invention:

[0031] Combine compound 1 (600 mg, 1.45 mmol) with 2,4-dinitrobenzenesulfonyl chloride (1.542 g, 5.8 mmol), triethylamine (804 μL, 5.8 mmol) in 30 mL of redistilled dichloromethane, ice After bathing for 1 hour, return to room temperature and stir for 16 hours. Add 30 mL of dichloromethane to dilute, wash with water (50 mL × 3), dry and evaporate the solvent by rotary evaporation, and use a mixed solvent of dichloromethane and methanol to separate the target compound PA-SN by column chromatography, yield: 50%. 1 H NMR (600 MHz, CDCl 3 ) δ(ppm): 8.68 (d, J = 1.8 Hz, 1H), 8.52 (dd, J = 8.6, 1.9 Hz, 1H), 8.41(s, 2H), 8.21(d, J = 8.6 Hz, 1H), 7.99 (d, J = 7.7 Hz, 1H), 7.84 (d, J = 8.7 Hz, 2H), 7.67(t, J = 7.5 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 6.63 (d, J = 8.9 Hz, 1H), 6.47(dd, J = 18.9, 10.0 Hz, 2H), 5.65 (s...

Example Embodiment

[0032] Example 3: Titration experiment of pH=7.4 fluorescent probe and biological thiol:

[0033] In PBS buffer pH=7.4, the fluorescent probe was added at an initial concentration of 2 mM, so that the concentration of the fluorescent probe in the solution was 10 μM. Then, different amounts of biothiols with an initial concentration of 20 mM were added sequentially, so that the concentrations of biothiols in the solution were 2 μM, 4 μM, 6 μM, 8 μM, 10 μM, 12 μM, 14 μM, and 16 μM, respectively. , 18 μM, 20 μM, 24 μM, 28 μM, 32 μM, 36 μM, 40 μM, 45 μM, 50 μM, 60 μM, 80 μM, 100 μM, 120 μM, 140 μM, 160 μM, 180 μM, 200 μM, 250 μM, 300 μM, 500 μM, and no biothiol was added as a control, and let stand for 0.5 hours to fully react the biothiol with the fluorescent probe. The absorption and fluorescence spectra of different biological thiols were tested with an absorption spectrometer and a fluorescence spectrometer, respectively. The excitation wavelength of the fluorescence spectrum...

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Abstract

The invention belongs to the technical field of organic small molecule fluorescent probes, and provides a fluorescent probe for detecting biological mercaptan in a water-soluble environment and a preparation method and application thereof. The molecular formula of the fluorescent probe is C32H26N3O10S<+>, the name of the probe compound is 4-(2-carboxyphenyl)-7-(diethylamino)-2-(4-(((2,4-dinitrophenyl) sulfonyl) oxy) phenyl) benzopyran, which is abbreviated as PA-SN, and the structural formula is shown in the specification. The preparation method of the fluorescent probe is simple. The probe has large fluorescence enhancement multiple and obvious color change, and can recognize the biological mercaptan with high selectivity in a water system, an organic solvent system and organisms. The fluorescence of the probe is weak and almost colorless in the organic system. After the probe is reacted with the biological mercaptan, the fluorescence of a solution increases significantly, and the color changes to purple obviously. The detection of the biological mercaptan is highly selective, sensitive and obvious.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule fluorescent probes, in particular to a fluorescent probe for detecting biothiols in a water-soluble environment and its preparation method and application. The fluorescent probe can be used in water-soluble, organic environments and cell environments Efficient identification of biothiols. Background technique [0002] Biothiols such as cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) play key roles in biological systems, and abnormal levels of these biothiols are associated with many diseases. Cys deficiency is associated with many syndromes such as slow growth in children, hair depigmentation, edema, lethargy, liver damage, muscle and fat loss, skin damage and weakness. GSH deficiency is also implicated in many diseases such as liver damage, loss of white blood cells, cancer, AIDS and neurodegenerative diseases. Therefore, rapid, convenient, selective and sensitive de...

Claims

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Application Information

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IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 李亚平乔柳琪蔡建华吕鑫
Owner SHANXI UNIV
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