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No-clean cell membrane targeting fluorescent probe and preparation method and application thereof

A technology for fluorescent probes and cell membranes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high probe production cost, cumbersome cleaning process, small Stokes shift, etc., and achieve simple post-processing , Reduce background interference, simple operation effect

Active Publication Date: 2020-08-14
WANNAN MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, although some cell membrane fluorescent dyes such as DiO, DiI, CellMask, etc. have been commercialized, the production costs of these probes are high, and there are problems in the actual application process. New economical and efficient cell membrane fluorescent probes still need to be developed urgently

Method used

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  • No-clean cell membrane targeting fluorescent probe and preparation method and application thereof
  • No-clean cell membrane targeting fluorescent probe and preparation method and application thereof
  • No-clean cell membrane targeting fluorescent probe and preparation method and application thereof

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Effect test

Embodiment 1

[0050] A no-wash type cell membrane targeting fluorescent probe, the no-wash type cell membrane targeting fluorescent probe is a pyridinium salt derivative, and its structural formula is:

[0051]

[0052] The preparation method and reaction formula of the no-wash cell membrane targeting fluorescent probe are as follows:

[0053]

[0054] Dissolve M1 (1.08g, 4mmol) and M2 (0.86g, 4mmol) in 20mL of acetonitrile, add 0.2mL of piperidine dropwise, and reflux for 14 hours. When the reaction solution was cooled to room temperature, a yellow solid powder precipitated out, which was filtered under reduced pressure. The filter cake was washed twice with a small amount of acetonitrile, and dried in vacuum for 24 hours to obtain 1.49 g of yellow solid Car-py with a yield of 80%.

[0055] References for the synthesis methods of compounds M1 and M2 (J Org Chem., 2013, 78, 3222-3234; Spectrochim Acta Part A Mol Biomol Spectrosc., 2017, 175, 92-99).

[0056] IR(KBr,cm -1 )selected b...

Embodiment 2

[0061] Application of no-wash cell membrane-targeted fluorescent probes in cell imaging

[0062] 1. Cell Membrane Identification

[0063] Plant human cervical cancer cells (HeLa cells) on small dishes (NEST product number: 801002), inoculate 10 cells per well 5 Cells can be used when the cell density grows to 60%. Formulate the compound Car-py into 10 -2 mol / L mother solution, the solvent is dimethyl sulfoxide, diluted to 10 μM with medium, and 2 mL is added to the well-cultured human cervical cancer cell (HeLa cell) in each well, and the 2 In a gas incubator at 37°C for 20 minutes, wash with PBS buffer solution twice, and then observe the results on the Leica TCS SP8 laser confocal microscope equipment, set the excitation wavelength to 405nm; figure 2 left and image 3 As shown in A1-A4, it can be seen from the figure that the compound Car-py can be precisely targeted to the cell membrane.

[0064] The cells after 20 minutes of incubation were not washed with PBS buffer...

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Abstract

The invention discloses a no-clean cell membrane targeting fluorescent probe and a preparation method and application thereof. Cheap carbazole monoaldehyde derivatives and 4-methylpyridinium containing sulfonate radicals are used for reaction, the compound pyridinium salt derivative Car-py with a D-pi-A conjugated structure is prepared, the fluorescent probe can be accurately positioned on a cellmembrane of a biological cell, the compound Car-py can be used for a developing test without cleaning after acting with the cell, the operation is simple, and the microstructure and dynamic change ofthe biological cell can be visually observed in real time through fluorescence microimaging.

Description

technical field [0001] The invention belongs to the technical field of molecular probes, and in particular relates to a wash-free cell membrane targeting fluorescent probe, a preparation method and application thereof. Background technique [0002] The cell membrane is composed of phospholipid bilayers embedded in proteins. Due to its selective permeability, it plays an important role in regulating material exchange and maintaining cell homeostasis. Meanwhile, the cell membrane is involved in various cellular processes and biological functions, including cell signal transduction, cell adhesion, endocytosis, exocytosis, etc. Cell membrane abnormalities are important biomarkers of cell states and various diseases, for example, cell membrane rupture or partial phagocytosis are important evidences of drug-induced apoptosis. Therefore, the observation of the microstructure of the cell membrane has important application value in the fields of cell biology, pharmacology, toxicolog...

Claims

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Application Information

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IPC IPC(8): C07D401/10C09K11/06G01N21/64
CPCC07D401/10C09K11/06G01N21/6428G01N21/6458C09K2211/1029C09K2211/1007
Inventor 王慧胡磊沈学彬许丙嵩陈浩蔡丰泽
Owner WANNAN MEDICAL COLLEGE
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