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Peptides

An oligopeptide and cyclic oligopeptide technology, which can be applied to peptides, cyclic peptide components, and resistance to vector-borne diseases, etc., can solve problems such as failure to generate active binding sites.

Inactive Publication Date: 2014-05-14
LEXICON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A second challenge is the need to design molecules that retain and provide the combination of amino acids that form this epitope, resulting in a strong binding interaction with the cellular receptor
[0009] The protein's binding site is composed of oligopeptides that are not adjacent to different parts of the protein chain. Attempts to reconstitute this binding site by mixing the separated free oligopeptide solutions failed to produce this active binding site

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: Cyclic oligopeptide inhibits the dose response of lipopolysaccharide (LPS) to stimulate macrophage cell lines to secrete TNF

[0114] 1. A cyclic octapeptide with the structural formula: cyclic (-DF-S-Σ-R-DF-S-Σ-R-) was synthesized by standard methods of Merrifield resin-based technology, and then cyclized in solution phase. A solution of this purified peptide was prepared in distilled water at a concentration of 1 mg / ml.

[0115] R, F and S represent epitope-forming amino acids, Σ represents the binding functional group on the binding amino acid, wherein the binding amino acid is L-α aminocarboxylic acid, and the binding functional group is an aliphatic straight chain containing 10 carbon atoms side chain residues.

[0116] All amino acids are in the L-form unless otherwise stated.

[0117] All amino acids are linked by peptide bonds.

[0118] 2. Inoculate J774A.1 cells (a macrophage cell line) in all wells of a 24-well colony plate at a seeding densit...

Embodiment 2

[0130] Example 2: Cyclic oligopeptides containing different binding functional groups inhibit the effect of cholera toxin B (CTB) fragments stimulating macrophage cell lines to secrete TNF

[0131] 1. Prepare a cyclic oligopeptide with the following structural formula:

[0132] Ring (-DF-R-∑ 10 -S-DF-R-∑ 10 -S-)

[0133] Ring (-DF-S-∑ 10 -R-DF-S-∑ 10 -R-)

[0134] Ring (-DF-R-∑ 4 -S-DF-R-∑ 4 -S-)

[0135]Ring (-DF-S-∑ 4 -R-DF-S-∑ 4 -R-)

[0136] In this formula, S, F and R represent epitope-forming amino acids, Σ represents the binding functional group on the binding amino acid, and Σ 10 Represents a racemic binding amino acid, which is an aminocarboxylic acid whose binding functional group consists of an unbranched -C 10 h 21 Constituent side chain residues, ∑ 4 Represents norleucine, where the binding functional group is a 4-carbon side chain.

[0137] These cyclic oligopeptides were made into a solution with a concentration of 5 mg / ml with diethylene glycol m...

Embodiment 3

[0144] Example 3: Cyclic oligopeptides containing different epitope-forming amino acids and binding amino acid stereochemical configurations inhibit the effect of lipopolysaccharide (LPS) stimulating the secretion of TNF from macrophage cell lines

[0145] 1. Preparation of a cyclic octapeptide with the following structural formula:

[0146] Ring (-DF-S-∑ L -R-DF-S-∑ L -R-)

[0147] Ring (-DF-S-∑ L -R-DF-S-∑ D -R-)

[0148] Ring (-DF-S-∑ D -R-DF-S-∑ D -R-)

[0149] Ring (-DF-R-∑ L -S-DF-R-∑ L -S-)

[0150] Ring (-DF-R-∑ L -S-DF-R-∑ D -S-)

[0151] Ring (-DF-R-∑ D -S-DF-R-∑ D -S-)

[0152] In this formula, F, S and R are epitope-forming amino acids, ∑ L Stands for a position-binding amino acid, which is an L-alpha aminocarboxylic acid in which the binding functional group is composed of unbranched-C 10 h 21 Constituent side chain residues; ∑ D Represents a binding amino acid, which is a D-α aminocarboxylic acid in which the binding functional group is compos...

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Abstract

An internally-constrained cyclic oligopeptide comprising a ring of at least six amino acids for specifically binding to a target ligand, wherein the ring comprises a plurality of amino acid domains, each domain comprising at least two epitope-forming amino acids, and two or more associating functional groups positioned so that they form one or more intra-cyclic associations; whereby the cyclic oligopeptide is constrained in a single conformation so that the epitope-forming amino acids form an epitope in each domain, each epitope being capable of specifically binding to a target ligand.

Description

[0001] The present invention relates to an internally constrained circular oligopeptide, a pharmaceutical composition containing the oligopeptide, the application of the oligopeptide and the pharmaceutical composition in medicine, and a method for preparing the oligopeptide. Background of the invention [0002] It is known that protein receptors generally bind to their target ligands through epitopes, which are combinations of amino acids and constitute a small part of protein macromolecules. [0003] Protein receptors on the cell surface are often triggered to generate a signal inside the cell, resulting in the binding of another protein called a protein ligand. The part of the ligand that interacts with the receptor is called an epitope, which usually consists of a small number of amino acids in close proximity to each other in the backbone of the peptide chain. Examples of epitopes are those structures on the surface of a protein that interact with antibodies or T-cell rece...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/52A61K38/12
CPCY02A50/30
Inventor R·纽
Owner LEXICON