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Peptide chain modified tetraphenylethylene derivative and preparation method and application thereof

A technology of tetraphenylethylene and derivatives, applied in the field of fluorescence imaging, can solve the problems of harmful organisms, cumbersome process, difficult modification of nanoparticles, and achieve good biocompatibility, good selective permeability, and increased solubility. and cell permeability

Pending Publication Date: 2021-02-23
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many steps in the preparation of nanoparticles, and the process is relatively cumbersome. The materials used to prepare nanoparticles are usually harmful to organisms.
Moreover, in practical applications, further modification of nanoparticles is required to facilitate cells to swallow nanoparticles, and the modification of nanoparticles is relatively difficult.

Method used

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  • Peptide chain modified tetraphenylethylene derivative and preparation method and application thereof
  • Peptide chain modified tetraphenylethylene derivative and preparation method and application thereof
  • Peptide chain modified tetraphenylethylene derivative and preparation method and application thereof

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preparation example Construction

[0057] In the present invention, when R is -H, the preparation method of the tetraphenylethylene derivatives modified by the peptide chain comprises the following steps:

[0058] Mix 4-(1,2,2-triphenylethenyl)benzaldehyde, a polypeptide containing cysteine ​​residues, and N,N-dimethylformamide for a nucleophilic addition-cyclization reaction, Obtain peptide chain-modified tetraphenylethylene derivatives;

[0059] Wherein, the structural formula of the polypeptide containing cysteine ​​residues is as follows:

[0060]

[0061] The reaction scheme is as follows:

[0062]

[0063] In the present invention, the molar ratio of the 4-(1,2,2-triphenylvinyl)benzaldehyde to the polypeptide containing cysteine ​​residues is preferably 1:(1~1.5), more preferably 1: (1~1.2). In the present invention, the N,N-dimethylformamide (DMF) is used as a solvent, and the dosage ratio of the N,N-dimethylformamide and the polypeptide containing cysteine ​​residues is preferably 2 mL: (0.033...

Embodiment 1

[0097] Preparation of tetraphenylethylene derivatives (referred to as compound I-1-i) modified with a peptide chain having a structure shown in formula I-1-i comprises the following steps:

[0098] Dissolve the polypeptide containing cysteine ​​residues (Peptidyl has the structure shown in formula i, 0.033mmol) and 4-(1,2,2-triphenylethenyl)benzaldehyde (0.04mmol) in N,N- In dimethylformamide (DFM, 2mL), the resulting mixture was stirred and reacted at room temperature (25°C) for 24h; after the reaction was completed, the resulting product system was slowly added to anhydrous ether (200mL) and allowed to stand for 12h A precipitate was precipitated, and then the filter cake was collected by filtration, washed with anhydrous ether, and dried to obtain the target product as a yellow solid.

[0099] Described target product is characterized, and the result is as follows:

[0100] MALDI-TOF:[M+H] + m / z 1356.7291 (found), 1356.7285 (calculated).

[0101] From the above molecular...

Embodiment 2

[0103] Preparation of a peptide chain modified tetraphenylethylene derivative (referred to as compound I-1-ii) having a structure shown in formula I-1-ii comprises the following steps:

[0104] Dissolve the polypeptide containing cysteine ​​residues (Peptidyl has the structure shown in formula ii, 0.036mmol) and 4-(1,2,2-triphenylethenyl)benzaldehyde (0.04mmol) in N,N- In dimethylformamide (2mL), the resulting mixture was stirred and reacted at room temperature for 24h; after the reaction, the resulting product system was slowly added to anhydrous ether (150mL), and left to stand for 12h to precipitate a precipitate, which was then collected by filtration The filter cake was washed with anhydrous ether and dried to obtain the target product as a yellow solid.

[0105] Described target product is characterized, and the result is as follows:

[0106] MALDI-TOF:[M+H] + m / z 1761.6886 (found), 1761.6869 (calculated).

[0107] From the above molecular weight data, it can be seen ...

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Abstract

The invention provides a peptide chain modified tetraphenylethylene derivative and a preparation method and application thereof, and belongs to the technical field of fluorescence imaging. TPE or a derivative thereof is marked on a polypeptide chain, the solubility and cell permeability of hydrophobic AIE molecules are improved, the obtained peptide chain modified tetraphenylethylene derivative isgood in water solubility, biocompatibility and selective permeability of a cytoplasmic membrane, a typical aggregation-induced emission (AIE) behavior is shown, dyeing imaging of a cytoplasmic regioncan be achieved, and the derivative can serve as a fluorescence probe molecule to be applied to the field of cell fluorescence imaging. The polypeptide chain is adopted as a modifying group, and thederivative has excellent biocompatibility and has great advantages compared with inorganic and organic nanoparticles of a polymer matrix or a silicon matrix with biotoxicity in the prior art.

Description

technical field [0001] The invention relates to the technical field of fluorescence imaging, in particular to a peptide chain-modified tetraphenylethylene derivative and a preparation method and application thereof. Background technique [0002] Fluorescence imaging technology is an important molecular imaging technology, which has the advantages of high sensitivity, fast response, convenient operation and real color imaging. The key to fluorescence imaging technology is to adjust the performance of fluorescent materials to make them suitable for imaging environment. The basic structures of existing aggregation-induced emission (AIE) molecules are mostly hydrophobic small organic molecules composed of aromatic rings and other groups, and their application in biological imaging is limited by many conditions. [0003] For example, the inherent strong hydrophobicity of small AIE organic molecules represented by tetraphenylethylene (TPE) makes it difficult for them to disperse ...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/02G01N21/64
CPCC07K7/06G01N21/6486
Inventor 孙景志倪珏宸童嘉琦
Owner ZHEJIANG UNIV
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