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Cell membrane imaging fluorescence probe and application thereof

A technology for fluorescent probes and cell imaging, which is applied in fluorescence/phosphorescence, luminescent materials, color/spectral characteristic measurement, etc., can solve problems such as poor stability and fluorescence quenching, and achieve good acid resistance, light stability, and stable fluorescence performance , The effect of stable fluorescence imaging performance

Active Publication Date: 2018-09-21
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

which uses Pb 2+ Complexation with compounds can increase the fluorescence intensity during cell imaging, but the complexes are poorly stable in acidic conditions and are easy to dissociate resulting in fluorescence quenching
It can be seen that the stable imaging of cell probes under acidic conditions is a great challenge.

Method used

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  • Cell membrane imaging fluorescence probe and application thereof
  • Cell membrane imaging fluorescence probe and application thereof
  • Cell membrane imaging fluorescence probe and application thereof

Examples

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Effect test

Embodiment 1

[0043] This embodiment proposes a cell membrane fluorescent probe containing pyranoside perylene imide derivatives, N -n-octyl- N’ -((4-Aminophenyl)- β -D-glucopyranoside)-3,4:9,10-peryleneimide, referred to as: PDI-OBAG, has the following molecular structure:

[0044]

[0045] The preparation method of fluorescent probe is as follows:

[0046] Add 0.5 g (0.99 mmol) N-octyl-3,4:9,10-perylenetetracarboxylic acid-3,4-anhydride-9,10-imine into a 100 mL round-bottomed flask, and add 0.35 g (4-aminophenyl)-β-D-glucopyranoside, 1.09 g zinc acetate, 15.0 g imidazole, under nitrogen protection, react at 160 °C for 2.5 h. After the reaction was stopped, cool to room temperature, transfer the reactant to a mixed solution of 480 mL of ethanol and 80 mL of water, stir, let it stand overnight, and filter with suction to obtain a red solid, which was dried in vacuo, and then washed with CH 2 Cl2 and a small amount of DMF washing, get N -n-octyl- N’ -((4-Aminophenyl)- β -D-glucopyr...

Embodiment 2

[0048] Application of cell membrane fluorescence imaging based on peryleneimide derivatives described in Example 1:

[0049] 1) Dissolving PDI-OBAG in PBS to obtain a working solution containing a fluorescent probe, the concentration of the fluorescent probe in the working solution is 10 μM;

[0050] 2) Use the working solution described in step 1) to incubate with SH-SY5Y cells for 25-35 min, and form a cell image after excitation; the wavelength of the excitation light is 605 nm.

[0051] Specific steps are as follows:

[0052] 1. The culture process of the SH-SY5Y cells:

[0053] 1. Recovery of SH-SY5Y cells

[0054] (1) Quickly place the cryopreservation tube of SH-SY5Y cells in warm water at 37 ℃, shake gently to melt it as soon as possible, and take out the cryopreservation tube after 30 seconds in the water bath;

[0055] (2) After sterilizing the outer surface of the cryovial with 75% alcohol, use a straw to suck out the cell suspension in the cryovial and pour it i...

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Abstract

The invention relates to a cell membrane imaging fluorescence probe, in particular to glycosyl-substituted perylene bisimide derivative cell membrane imaging dye. An alkyl chain is introduced into oneend of the derivative, and pyranose is introduced into the other end. The dye can be self-assembled into nano-particles in vitro and enter cells, and then are redistributed in cell membranes, and after the dye is excited, the cell membranes can be specifically imaged. Compared with traditional cell membrane fluorescence dye, the dye is high in biocompatibility and lasting in light and acid stability, and the preparation method is simple, economical and capable of being widely used in cell membrane imaging research, especially, the research on imaging of the cell membranes of tumor cells in aweak acid environment.

Description

technical field [0001] The invention belongs to the technical field of molecular probes, and in particular relates to a fluorescent probe for cell membrane imaging and an application thereof. Background technique [0002] The cell membrane, also known as the cytoplasmic membrane, is a double-layer membrane with a thickness of about 7.5 nm surrounding the cell surface in eukaryotic cells. The cell membrane not only constitutes the boundary of the cell structurally and enables the cell to form a stable internal environment, but also plays an important role in the process of material transport and information and energy exchange between the cell and the external environment. In addition, the cell membrane is also closely related to important cell biological behaviors such as cell adhesion, extension, division, proliferation, endocytosis, efflux, apoptosis, and necrosis. When researchers study the function of cell membranes, they need to use relevant tools, among which the most...

Claims

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Application Information

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IPC IPC(8): C07H15/26C07H1/00C09K11/06G01N21/31G01N21/64
CPCC07H1/00C07H15/26C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/31G01N21/6486
Inventor 黄永伟刘中华刘芳李晓王俊超
Owner HENAN UNIVERSITY
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