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A kind of polypeptide imaging probe and its preparation method and application

A technology for imaging probes and peptides, which is applied in the fields of polypeptide imaging probes and their preparation, in situ self-assembly polypeptide imaging probes for identifying cell receptors and their preparation, and can solve the problem of large molecular weight probes and limited imaging probes. The scope of application, the inability to enter efficiently, etc., to achieve the effect of enhancing the imaging signal-to-noise ratio, good aggregation retention ability, and simple structure

Active Publication Date: 2022-08-09
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the imaging probe has an enzyme-substrate unit, which makes the molecular weight of the probe large and cannot enter cells efficiently, and the substrate needs to react with a high concentration of enzyme around the lesion to trigger the self-assembly of the probe, which limits the applicability of the imaging probe scope

Method used

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  • A kind of polypeptide imaging probe and its preparation method and application
  • A kind of polypeptide imaging probe and its preparation method and application
  • A kind of polypeptide imaging probe and its preparation method and application

Examples

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Embodiment 1

[0073] Example 1 Design, synthesis and functional identification of polypeptide imaging probe αvβ3-Cy

[0074] In this example, a polypeptide imaging probe αvβ3-Cy is designed with αVβ3 as the targeting receptor. The polypeptide imaging probe αvβ3-Cy is composed of a αVβ3 receptor recognition peptide, a soluble self-assembling peptide and a near-infrared fluorescent molecule Cy. The near-infrared fluorescent molecule Cy is connected to the side chain of the polypeptide through cysteine ​​(C), and the molecular structure is as follows figure 2 As shown, the amino acid sequence is shown in SEQ ID NO: 14;

[0075] SEQ ID NO: 14: GNNQQNYKC(Cy7)DRGD.

[0076] The synthesis steps are as follows:

[0077] (1) Weigh the resin and put it into the peptide solid-phase synthesis tube, add an appropriate amount of DMF to swell for more than 4 hours; extract the DMF, use the Fmoc deprotection agent for Fmoc deprotection, and mix on a shaker for 15 minutes; extract the Fmoc deprotection a...

Embodiment 2

[0087] Example 2 Design, synthesis and functional identification of polypeptide imaging probe EpCAM-Cy

[0088] In this example, a polypeptide imaging probe EpCAM-Cy is designed with EpCAM as the targeting receptor. The polypeptide imaging probe EpCAM-Cy is composed of EpCAM receptor recognition peptide, soluble self-assembling peptide and near-infrared fluorescent molecule Cy. The near-infrared fluorescent molecule Cy is connected to the side chain of the polypeptide through cysteine ​​(C), and the molecular structure is as follows Figure 5 As shown, the amino acid sequence is shown in SEQ ID NO: 15;

[0089] SEQ ID NO: 15: GNNQQNYKC(Cy7)DYEVHTYYLD.

[0090] The synthetic method is shown in Example 1.

[0091] to about 10 5 Breast cancer cell lines MCF-7 and 10 with high expression of epithelial cell adhesion molecule EpCAM 5 1 mL of 20 μM polypeptide imaging probe EpCAM-Cy was added to HUVEC, a human umbilical vein endothelial cell line with low expression of the epithe...

Embodiment 3

[0096] Example 3 Design, synthesis and functional identification of polypeptide imaging probe αvβ3-NBD

[0097] Compared with near-infrared fluorescent molecules, the in vivo imaging effect of short-wavelength fluorescent molecules is slightly insufficient, but the imaging effect of cells is more stable and not easy to be quenched. In this example, NBD, a molecule with aggregation-induced luminescence effect, is used instead of the near-infrared fluorescent molecule Cy7 to perform fluorescence imaging at the cell level, which has the advantages of no washing, high signal-to-noise ratio, and can qualitatively characterize the expression of cell surface receptors.

[0098] The molecular structural formula of the polypeptide imaging probe αvβ3-NBD in this example is as follows: Figure 8 As shown, the amino acid sequence is as shown in SEQID NO:16, wherein X is Fmoc aminovaleric acid;

[0099] SEQ ID NO: 16: NBD-X-GNNQQNYRGD.

[0100] The synthesis method is shown in Example 1....

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Abstract

The invention provides a polypeptide imaging probe and its preparation methods and applications that include the polypeptide imaging probe includes receptor recognition peptides, self -assembly peptides and signal molecules;Combine with receptor recognition, trigger self -assembly peptides, and signals by signal molecules.The polypeptide imaging probe of the present invention responds to the formation of nano fiber by the tumor micro -environment. Compared with small molecule imaging agents, it has the advantages of high -rich and long -staying.It has a long -term retention effect, presents a high signal -to -noise ratio in the targeted part, and the required dose is low, which significantly reduces the toxicity of metabolic organs, and provides new ideas and new methods for the transformation and development of imaging.

Description

technical field [0001] The invention belongs to the technical field of nanometer biomedicine, and relates to a polypeptide imaging probe, a preparation method and application thereof, and in particular to an in-situ self-assembled polypeptide imaging probe for recognizing cell receptors, a preparation method thereof, and an imaging probe in cell imaging and / or cell imaging. or applications in in vivo imaging. Background technique [0002] Malignant tumors (cancer) are diseases that seriously threaten human life and health. In the clinical treatment of cancer, the use of imaging probes to image tumor lesions is beneficial for the purposes of early diagnosis, lesion localization, and intraoperative navigation. However, traditional small molecule imaging agents such as indocyanine green (ICG), methylene blue (MB), etc. have the disadvantages of low enrichment efficiency, short retention time, weak fluorescence signal-to-noise ratio, and high dosage, which may lead to false pos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K19/00C07K1/13C09K11/06C09K11/02G01N21/64A61K49/00
CPCC07K5/0817C07K7/06C07K7/08C09K11/06C09K11/025G01N21/6428G01N21/6458A61K49/0056C07K2319/735C09K2211/1029C09K2211/1048C09K2211/1044G01N2021/6432
Inventor 王浩安红维王曼迪吕甘田
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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