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Fluorescent probe used for cell membrane imaging, and preparation method and application of fluorescent probe

A technology of fluorescent probes and cell membranes, which is applied in the preparation methods of peptides, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of poor stability and specificity, and achieve high photostability, convenient operation, and non-permeation sex high effect

Active Publication Date: 2021-09-24
CHINA UNIV OF GEOSCIENCES (WUHAN)
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, due to the complex and dynamic nature of cell membranes, conventional fluorescent probes that utilize only one or two weak interactions are less specific and less stable when labeling cell membranes.

Method used

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  • Fluorescent probe used for cell membrane imaging, and preparation method and application of fluorescent probe
  • Fluorescent probe used for cell membrane imaging, and preparation method and application of fluorescent probe
  • Fluorescent probe used for cell membrane imaging, and preparation method and application of fluorescent probe

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preparation example Construction

[0032] In addition, the present invention also provides a method for preparing a fluorescent probe for cell membrane imaging, comprising the following steps:

[0033] Step S1: Dissolving the pure polypeptide RP-C and the sulfhydryl reducing agent tris(2-carboxyethyl)phosphine in phosphate buffered saline solution, and reacting at room temperature under nitrogen protection;

[0034] Step S2: Add molecular tetraphenylethylene derivatives with aggregation-induced luminescent effect, and stir for reaction;

[0035] Step S3: Obtain polypeptide aggregates through purification.

[0036] In step S1, the pure polypeptide RP-C and the sulfhydryl reducing agent tris(2-carboxyethyl)phosphine are dissolved in phosphate buffered saline solution, and the tris(2-carboxyethyl)phosphine can prevent the sulfhydryl group of the pure polypeptide RP-C from being oxidized into disulfide bond, the phosphate buffered saline solution can prevent the ring-opening of the maleimide group of the tetraphen...

Embodiment 1

[0044] 1. Synthesis of fluorescent probes for polypeptide aggregates:

[0045] Add MTY (9.0mg, 20μmol), RP-C (17.4mg, 10μmol), tris(2-carboxyethyl)phosphine (1.4mg, 5μmol), dimethyl sulfoxide 2mL, PBS buffer in a 100mL round bottom flask solution 2mL, under the protection of nitrogen atmosphere, stirred and reacted at room temperature for 24 hours to obtain a crude product, which was purified by high performance liquid chromatography and freeze-dried to obtain the product polypeptide aggregate fluorescent probe (17.5 mg, yield: 80%).

[0046] The polypeptide aggregate fluorescent probe prepared above was characterized by high-resolution mass spectrometry, which confirmed the structure of the probe, and its mass spectrometry characterization was as follows: figure 2 shown.

[0047] HRMS(ESI)m / z:[M+3H] 3+ Calculated value: 730.7507, measured value: 731.0847; [M+4H] 4+ Calculated value: 548.3149, measured value: 548.5655; [M+5H] 5+ Calculated value: 438.8533, measured value: 4...

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Abstract

The invention provides a fluorescent probe used for cell membrane imaging, and a preparation method and application of the fluorescent probe. The structural formula of the fluorescent probe consists of three parts: polypeptide RGD, a tetraphenyl ethylene derivative MTY and palmitic acid modified polypeptide Pal-RRRR; the RGD is combined with integrin protein on a cell membrane through ligand-receptor interaction; Pal is inserted into lipid on the cell membrane through hydrophobic interaction; and the RRRR is combined with the cell membrane with negative charges through electrostatic interaction, so that accurate and firm imaging of the cell membrane is realized. The fluorescent probe has the characteristics of high light stability, high fluorescent brightness, high impermeability and the like, and can carry out rapid imaging; and in addition, the fluorescent probe shows an obvious aggregation-induced luminescence phenomenon and excellent photobleaching resistance in practical application, can realize long-time fluorescence imaging, has the characteristics of a simple preparation technology, convenience in operation and a low cost, and has a huge application prospect in the field of biomedical imaging.

Description

technical field [0001] The invention relates to the technical field of molecular probe applications, in particular to a fluorescent probe for cell membrane imaging, a preparation method and application thereof. Background technique [0002] Fluorescence imaging has the advantages of low cost, good biocompatibility and high sensitivity, so it is widely used in the field of biomedical imaging. The cell membrane is the outermost layer of the cell and acts as a barrier that protects the cell from external damage. At the same time, the cell membrane plays an important role in many biochemical processes, such as maintaining the stability of the intracellular environment, controlling the transport of substances between the cell and the surrounding environment, coordinating energy conversion, and regulating signal transduction, etc. At present, cell membrane fluorescent labeling is the simplest and most important method in cell membrane research. It can not only visually observe th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/08C07K1/107C09K11/06G01N21/64
CPCC07K7/08C09K11/06G01N21/6428G01N21/6458C09K2211/1425C09K2211/1466G01N2021/6439
Inventor 娄筱叮杨聚梁胡晶晶夏帆
Owner CHINA UNIV OF GEOSCIENCES (WUHAN)
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