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BODIPY derivative with cell membrane labeling function and used for single-molecule positioning super-resolution imaging and single-molecule tracking and application thereof

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: 2021-08-06
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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  • BODIPY derivative with cell membrane labeling function and used for single-molecule positioning super-resolution imaging and single-molecule tracking and application thereof
  • BODIPY derivative with cell membrane labeling function and used for single-molecule positioning super-resolution imaging and single-molecule tracking and application thereof
  • BODIPY derivative with cell membrane labeling function and used for single-molecule positioning super-resolution imaging and single-molecule tracking and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] 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

[0027]

[0028]Synthesis 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 a 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

[0030]

[0031] Synthetic method: Dissolve bis(p-piperazinylphenyl)vinylfluoroboropyrrole (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 three times with dichloromethane or n-hexane 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

The invention discloses a BODIPY derivative with a cell membrane labeling function and used for single-molecule positioning super-resolution imaging and single-molecule tracking and application thereof, and belongs to the field of fine chemical engineering. The BODIPY derivative has excellent photo-physical properties, and has good brightness and stability. Meanwhile, due to introduction of double bonds, cis-trans isomerism change can occur under the condition of high laser irradiation, so that light conversion in bright and dark states is realized, and single-molecule positioning super-resolution imaging is facilitated. The dye is designed into an amphiphilic molecular structure and can be retained on a cell membrane for a long time, and meanwhile, a BODIPY fluorophore tends to enter the inner side of a phospholipid molecular layer, so that a long-range bright state can be realized, and tracking analysis of a single molecule is facilitated. The dye can be used for realizing simultaneous imaging of the ultra-structure and fluidity of living cells under a non-imaging liquid condition, and the imaging has ultrahigh temporal-spatial resolution and reveals important characteristics of a membrane, so that the derivative can be used for realizing molecular diagnosis of a cell membrane structure. The new diagnosis information can improve the diagnosis accuracy and precision, and has important application prospects in molecular-scale diagnosis and treatment.

Description

technical field [0001] The invention relates to 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 application, belonging 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 membran...

Claims

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Application Information

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Patent Type & Authority Applications(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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