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Cyclic peptide compound and application thereof

A compound and cyclic peptide technology, applied in the field of cyclic peptide compounds and their applications, can solve the problems of low clinical response rate and immune-related inflammation, and achieve the effects of reducing immune-related side effects, inhibiting interactions, and promoting killing

Active Publication Date: 2020-11-20
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs still have the disadvantages of low clinical response rate and severe immune-related inflammation and other toxic side effects.

Method used

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  • Cyclic peptide compound and application thereof
  • Cyclic peptide compound and application thereof
  • Cyclic peptide compound and application thereof

Examples

Experimental program
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preparation example Construction

[0046] The preparation method of above-mentioned cyclic peptide compound comprises the following steps:

[0047] (1) Synthesize linear peptides protected by side chains. The synthesis steps are as follows: take 0.5g of 2-chlororityl chloride resin, add it to a reactor with a filter element, add 10mL of dry dichloromethane to swell for 30min, remove the solvent, add the second An amino acid raw material (3eq.) that needs to be uploaded, diisopropylethylamine (3eq.), dichloromethane as a solvent, and react at room temperature for 3h. The main chain amino group of the amino acid raw material is protected by Fmoc. If the amino acid side chain has active groups, it needs to be protected by a protecting group suitable for the Fmoc / tBu synthesis strategy. If R 7 for -OCO-(CH 2 ) n CH 3 (n=a positive integer of 0 to 18), wherein the threonine needs to be protected with fatty acids of different lengths in the side chain, and the threonine raw material whose amino group is protected...

Embodiment 1

[0052] As a cyclic peptide compound according to an embodiment of the present invention, the structural formula of the cyclic peptide compound is shown in Formula II, The name of the cyclic peptide compound shown in formula II is cyclo(-Leu-DPhe-Pro-Ala-Asp-Leu-DPhe-Pro-Val-Arg-), with respect to the general formula of the peptide compound shown in formula I, R 1 =-CH 3 , R 2 =-CH 2 CH(CH 3 ) 2 , R 3 with R 4 concatenated as -CH 2 CH 2 CH 2 -and-CH 2 CH 2 CH 2 - with the R 3 , R 4 The C-N bond where it is connected is a five-membered heterocyclic ring containing a nitrogen, R 5 =-CH(CH 3 ) 2 , R 6 =-CH 2 C 6 h 5 .

[0053] The preparation method of the cyclic peptide compound of the present embodiment comprises the following steps:

[0054] (1) Synthesize the linear peptide Leu-DPhe-Pro-Ala-Asp(OtBu)-Leu-DPhe-Pro-Val-Arg(Pbf), the specific steps are: get 0.5g 2-chlororityl chloride resin, add the In the reactor, add dry dichloromethane 10mL to swell for...

Embodiment 2

[0059] As a cyclic peptide compound according to an embodiment of the present invention, the structural formula of the cyclic peptide compound is shown in formula III, The name of the compound shown in formula III is cyclo (-Leu-DPhe-Pro-Ala-Asp-Ala-DPhe-Pro-Val-Arg-), with respect to the general formula of the peptide compound shown in formula I, R 1 =-CH 3 , R 2 =-CH 3 , R 3 with R 4 concatenated as -CH 2 CH 2 CH 2 -and-CH 2 CH 2 CH 2 - with the R 3 , R 4 The C-N bond where it is connected is a five-membered heterocyclic ring containing a nitrogen, R 5 =-CH(CH 3 ) 2 , R 6 =-CH 2 C 6 h 5 .

[0060] The difference between the preparation method of the cyclic peptide compound of this example and Example 1 is: 1, the synthesis of the linear peptide compound Leu-DPhe-Pro-Ala-Asp(OtBu)-Ala-DPhe-Pro-Val-Arg(pbf), 2. Depending on the linear peptide sequence during synthesis, the amino acid raw materials uploaded in sequence are different.

[0061] The product a...

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Abstract

The invention provides a cyclic peptide compound and application thereof. A structural formula of the cyclic peptide compound is disclosed by a formula I. The cyclic peptide compound disclosed by theinvention can obviously inhibit mutual action of a programmed death ligand 1 (PD-1) and a programmed death receptor 1 (PD-L1), and in addition, the cyclic peptide compound disclosed by the invention can obviously accelerate PBMC (Peripheral blood mononuclear cell) to kill tumor cells. In addition, the cyclic peptide compound disclosed by the invention can obviously lower the tumor growth speed ofa tumor-bearing animal and tumor quality so as to display that the cyclic peptide compound disclosed by the invention can accelerate a killing function of the immune system for tumor through the obstruction of an immunosuppression effect in tumor environment. In addition, the cyclic peptide compound disclosed by the invention can lower the content rise of cell factor IFN-[gamma] and IL-10 due to Tcell activation so as to display that an immunity related side effect can be reduced.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a cyclic peptide compound and its application. Background technique [0002] Malignant tumors seriously endanger human health. Although traditional treatment methods such as surgery, radiotherapy, and chemotherapy have been widely used clinically, they still have serious defects such as drug resistance, toxic side effects, and damage to the immune system. In recent years, tumor immunotherapy, which uses the body's own immune system to kill tumors and inhibit tumor growth, has attracted much attention. Chemotherapy, radiotherapy and targeted therapy are an emerging treatment method, which has become a hot spot in current anticancer drug research. Among them, restoring the anti-tumor immune effect by blocking immune checkpoint-related proteins has attracted widespread attention. [0003] Programmed death ligand 1 (programmed death ligand-1, PD-L1) is expressed on most tumor cells and immu...

Claims

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Application Information

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IPC IPC(8): C07K7/06A61K38/12A61P35/00
CPCC07K7/06A61P35/00A61K38/00
Inventor 卜宪章孙海霞伍伟健
Owner SUN YAT SEN UNIV
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