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A class of fluborazole derivatives with cell membrane labeling function for single-molecule positioning super-resolution imaging and single-molecule tracking and applications

A technology with super-resolution imaging and labeling functions, applied in the field of fine chemical industry, can solve the problems of difficult to achieve high-density positioning super-resolution imaging, dyes cannot exhibit bright and dark state transition characteristics, etc., and is conducive to single-molecule tracking analysis, realization Long-range bright state, the effect of improving diagnostic accuracy and precision

Active Publication Date: 2022-03-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the dyes under this strategy cannot exhibit bright-dark state transition characteristics, making it difficult to achieve high-density localized super-resolution imaging

Method used

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  • A class of fluborazole derivatives with cell membrane labeling function for single-molecule positioning super-resolution imaging and single-molecule tracking and applications
  • A class of fluborazole derivatives with cell membrane labeling function for single-molecule positioning super-resolution imaging and single-molecule tracking and applications
  • A class of fluborazole derivatives with cell membrane labeling function for single-molecule positioning super-resolution imaging and single-molecule tracking and applications

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Synthesis of 2,4,6,8-tetramethylfluoroboron pyrrole: synthesized according to the method in the literature, dissolving pyrrole in dry dichloromethane, adding benzoyl chloride dropwise in an inert gas atmosphere, and reacting in the dark 2-3h, after the reaction is complete, add triethylamine to adjust the pH to neutral, and then add boron trifluoride ether for coordination to obtain boron pyrrole. After the product is washed with water to remove boron trifluoride ether, pass column chromatography Isolation and Purification.

Embodiment 2

[0028]

[0029] Synthetic method: Dissolve the mixture of fluborazole (500mg, 1.54mmol) and p-methylpiperazine benzaldehyde (788mg, 3.88mmol) in toluene (50mL), add piperidine (3mL) in an inert gas atmosphere, and stir for 30min Afterwards, additional glacial acetic acid (3 mL) was added. Heating to reflux, using the water separator to separate the water produced in the reaction process, so that the reaction proceeds gradually to the right. Use TLC to detect the degree of completion of the reaction. After the conversion is complete (about 50-60 h), the reaction can be stopped and purified by column chromatography (dichloromethane:methanol=15:1) to obtain 706 mg of the product with a yield of 66.1%. The product structure was identified by HRMS, m / z=349.2036(z=2).

Embodiment 3

[0031]

[0032] Synthetic method: Dissolve bis(p-piperazinylphenyl)vinylfluoroborate (50 mg, 71.8 μmol) in 20 mL of N,N-dimethylformamide, add methyl iodide (447 μL, 7.18 mmol) dropwise, and stir at room temperature Reaction 48h. After completion of the reaction, wash with dichloromethane or n-hexane three times to obtain 52 mg of BDP1 (yield 99.7%). The product structure was identified by HRMS, m / z=363.2187 (z=2).

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Abstract

A class of fluborazole derivatives with the function of cell membrane labeling for single-molecule positioning super-resolution imaging and single-molecule tracking and their applications belong to the field of fine chemicals. The boropyrrole derivative has excellent photophysical properties, and has good brightness and stability. At the same time, due to the introduction of double bonds, the dye can undergo cis-trans isomerization under high laser irradiation conditions, thereby realizing light-to-dark state photoconversion, which is beneficial to single-molecule positioning super-resolution imaging. The dye is designed as an amphiphilic molecular structure, which can remain on the cell membrane for a long time. At the same time, the fluoroborate fluorophore itself tends to enter the inner side of the phospholipid molecular layer, which can achieve a long-range bright state, which is beneficial to single-molecule tracking analysis. Therefore, the dye can be used to simultaneously image the ultrastructure and fluidity of living cells under non-imaging fluid conditions. The imaging has ultra-high spatial and temporal resolution and reveals important features of the membrane. Molecular diagnostics of cell membrane structure.

Description

technical field [0001] The invention relates to a class of fluoroboryrrole derivatives with the function of cell membrane labeling for single-molecule positioning super-resolution imaging and single-molecule tracking and their applications, which belong to the field of fine chemicals. Background technique [0002] The cell membrane is a key component of cells, providing a barrier for cell physiological metabolism and deeply involved in cell differentiation, autophagy, apoptosis and aging processes. Its main component is phospholipid, which forms the main structure of the membrane in a bilayer configuration, with anisotropic fluidity and aggregation characteristics; the components of the cell membrane also include adhesion or transmembrane proteins with different functions, and adhesion to the surface multi-conformational sugar chains. The complex structure formed by these various components works together on the surface to realize various physiological functions of the cell...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428G01N21/6486G01N21/6456C09K2211/1055C09K2211/1044
Inventor 肖义叶智伟杨薇
Owner DALIAN UNIV OF TECH
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