HOCl fluorescent probe based on pyronin hydrazine, preparation method and application

A technology of fluorescent probe and pyrrolizine, applied in the field of fluorescent probe, can solve the problems of lack of specificity and sensitivity, and achieve the effect of remarkable response and high sensitivity

Active Publication Date: 2021-04-23
SHANXI UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

Due to the lack of sufficient specificity and sensitivity of traditional diagnostic methods for cancer (such as angiography, CT examination, magnetic resona

Method used

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  • HOCl fluorescent probe based on pyronin hydrazine, preparation method and application
  • HOCl fluorescent probe based on pyronin hydrazine, preparation method and application
  • HOCl fluorescent probe based on pyronin hydrazine, preparation method and application

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Embodiment

[0050] (1) Dissolve xanthone (1.01 g, 3 mmol) in anhydrous tetrahydrofuran (30 mL) at 0 °C under nitrogen atmosphere, and slowly add methylmagnesium bromide (3.75 mmol) to the above reaction solution THF solution, stirred overnight at room temperature, quenched with water (50 mL), extracted with DCM (3×50 mL), and removed the solvent under reduced pressure. After 1 min, it was extracted again with DCM (3 × 50 mL), and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration and evaporation gave the crude product, which was purified by column chromatography to give Intermediate 2 (1.05 g, 80%).

[0051] 1H NMR (600 MHz, CDCl3) δ 7.96 (d, J = 9.6 Hz, 2H), 7.03 (d, J = 9.6Hz, 2H), 6.70 (s, 2H), 3.63 (q, J1 = 7.2 Hz, J2 = 6.6 Hz, 8H), 2.88 (s, 3H), 1.34 (t, J = 6.6 Hz, 12H); 13C NMR (150 MHz, CDCl3) δ 152.39, 140.597, 123.53, 123.06, 115.71, 115.02, 66.783, 49. , 21.55; ESI-MS [M+H]+: calcd for337.2274, Found 337.2276.

[0052] (2) Intermediate 2 (1.5 g, 3.43 m...

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Abstract

The invention provides an HOCl fluorescent probe based on pyronin hydrazine, a preparation method and application. The structural formula of the probe is shown as a formula I and a formula II. According to the invention, the probe is constructed by combining a hydrazine reaction site and a pyronin fluorophore, has extremely low background fluorescence due to C=N isomerization and the PET process, provides rapid and significant fluorescence off-on response to HClO in the red light region, has extremely high sensitivity, and has been successfully used for distinguishing cancer cells/tissues from normal cells/tissues.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a pyrolorubin-based HOCl fluorescent probe, a preparation method and an application. Background technique [0002] In view of the characteristics of high sensitivity, visualization, biocompatibility, no radiation, and real-time detection, fluorescence technology has become an indispensable research method in the fields of biology and medicine. Especially in the past ten years, with the development of life sciences, the continuous breakthrough of fluorescent imaging equipment, and the successive development of various new fluorescent dyes and probe molecules, this technology has expanded from the detection of ions, small biological molecules, enzymes, etc. Fast, three-dimensional microscopic imaging of cells, tissues, and living animals. Not only that, fluorescence technology has also made important progress in the diagnosis and treatment of cancer in recent years. With the help...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D417/12C09K11/06G01N21/64A61K49/00
CPCC07D417/12C07D405/12C09K11/06G01N21/6428A61K49/0041C09K2211/1037C09K2211/1029C09K2211/1088G01N2021/6439
Inventor 刘景王林芳郭炜
Owner SHANXI UNIV
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