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A kind of peptide and its preparation method and use

A kind of technology of medicinal salts, applied in the field of biomedicine, can solve the problems of large toxic and side effects, easy to cause adverse reactions, poor selectivity, etc.

Active Publication Date: 2022-04-29
BEIJING BOE TECH DEV CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditionally, the currently clinically used antineoplastic drugs are mainly cytotoxic chemotherapeutic drugs, but these drugs have poor selectivity, high toxicity and side effects, and are likely to cause adverse reactions
Although protein drugs such as antibodies have high specificity and low toxic and side effects, they are difficult to provide for ordinary tumor patients due to their large molecular weight, complex structure, easy to cause immune response and drug resistance, and their preparation process is complicated so that the price is high. bear

Method used

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  • A kind of peptide and its preparation method and use
  • A kind of peptide and its preparation method and use
  • A kind of peptide and its preparation method and use

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Experimental program
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preparation example Construction

[0052] At least one embodiment of the present disclosure also provides a preparation method of a peptoid, the preparation method comprising the following steps:

[0053] (1) The compound of formula II reacts with the amino group at the end of the solid-phase carrier resin to form an amide bond;

[0054]

[0055] Wherein, R is OH or Cl;

[0056] (2) adding a subunit to replace the bromine atom through a nucleophilic substitution reaction;

[0057] (3) Steps (1) and (2) are repeated until the synthesis of all subunits is completed,

[0058] Wherein, the input order of the subunits is: cysteine, monoprotected tetramethylenediamine, monoprotected tetramethylenediamine, β-alanine, ethanolamine, monoprotected tetramethylenediamine Diamine, isobutylamine, the single protection refers to the protection of an amino group in the diamine by an amino protecting group;

[0059] (4) Remove the amino protecting group of the side chain, and cleave the peptoid from the resin.

[0060] I...

Embodiment 1

[0088] The preparation of embodiment 1 formula I class peptide

[0089] The peptoids are synthesized by solid phase synthesis, the method comprising the following steps:

[0090] (1) Soak Rink amide AM resin (substitution level 0.3mmol / g, 200mg) in N,N-dimethylformamide (DMF), fully swell for 15 minutes and discharge the DMF solution;

[0091] (2) Deprotection: configure a DMF solution of 20% hexahydropyridine, immerse the resin in excess deprotection solution and react for 10 minutes, and the Fmoc protecting group is removed to expose free amino groups;

[0092] (3) cleaning resin: alternately cleaning each 3 times with dichloromethane (DCM), DMF;

[0093] (4) Add 2M bromoacetic acid in DMF (2.5ml) and 3.2M N,N'-diisopropylcarbodiimide (DIC) in DMF (2.5ml) to Rink amide AM resin, at 37°C React for 30 minutes to acylate the amino group at the end of the resin;

[0094] (5) Add 2M DMF solution (5 ml) of the subunit to be added and react at 37° C. for 90 minutes to replace th...

Embodiment 2

[0099] Example 2 Peptide Molecular Probe EpCAM Highly Expressed Cell Line Specific Targeting Experiment

[0100] The specific steps for cellular level imaging using fluorescently labeled peptide-like molecular probes are as follows:

[0101] (1) Cell culture and subculture: the cell models were selected as Huh7 cell line with high expression of EpCAM protein and human embryonic kidney 293T cell line with low expression of EpCAM (Shanghai Enzyme Biotechnology Co., Ltd.). Huh7 and 293T cells were respectively used with 10 % fetal bovine serum and 1% penicillin and streptomycin RPMI1640 medium and DMEM / High glucose medium in a constant temperature incubator at 37°C (5% CO 2 ) cultured in;

[0102] (2) When the cell confluency reaches more than 90%, subculture the cells, suck up the medium with a pipette, wash off the residual medium and cell debris with PBS, and then add 0.25% trypsin 37 containing EDTA Digest at ℃ for 2 minutes, add medium containing serum to stop digestion, c...

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Abstract

Embodiments of the present disclosure provide a peptoid, which is a compound of formula I or a pharmaceutically acceptable salt thereof, N-R in formula I 4 , N‑R 3 , N‑R 2 , N‑R 1 These peptides have a strong binding ability to EpCAM protein, and they can be used as molecular probes for diseases related to EpCAM protein, and realize targeted therapy and in-vivo imaging diagnosis of diseases related to EpCAM protein at low cost, accurately and efficiently and prognostic monitoring.

Description

technical field [0001] The present disclosure relates to the field of biomedical technology. In particular, embodiments of the present disclosure relate to a peptoid and its preparation method and use. Background technique [0002] Epithelial cell adhesion molecule (EpCAM) is a single transmembrane protein encoded by the tumor-associated calcium signal transducer 1 (TACSTD1) gene, which belongs to the adhesion molecule family and participates in the regulation of Cell-to-cell adhesion, mediating functions such as signal transduction, cell migration, proliferation and differentiation. Pathologically, EpCAM is expressed in almost all adenocarcinomas, including colorectal adenocarcinoma, gastric adenocarcinoma, breast cancer, ovarian cancer, lung adenocarcinoma, prostate cancer, pancreatic cancer and retinoblastoma. EpCAM activates the expression of proto-oncogenes such as c-myc gene and cyclin A / E by participating in the β-catenin-dependent Wnt cascade reaction, and has a tu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/04A61K38/08A61P35/00G01N33/68G01N33/574G01N33/569A61K49/00
CPCC07K7/06A61P35/00G01N33/68G01N33/57492G01N33/56966A61K49/0056A61K38/00G01N2333/70525A61K38/08Y02P20/55C07K1/061G01N33/54366G01N33/582
Inventor 赵子健
Owner BEIJING BOE TECH DEV CO LTD
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