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Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof

An immunosuppressant, synthetic technology, applied in the fields of peptides, organic chemistry, drug combination, etc., can solve the problems of difficult chemical synthesis and unfavorable purification, and achieve the effect of stable physical and chemical properties and high purity

Active Publication Date: 2010-09-08
CHINESE PEPTIDE CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The amino acid residues in the natural structure of HS-1 are all hydrophobic amino acids, and the sequence is rich in Pro with a secondary amine ring structure, which makes chemical synthesis extremely difficult and is also very unfavorable for purification

Method used

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  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof
  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof
  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof

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Abstract

The invention relates to a cyclic peptide which is provided with a residue fragment of -Val-Sta-Leu- and is used as immunosuppressive agents, and the synthesis process of the cyclic peptide (Ile-Ile-Pro-Pro-Tyr-Val-Sta-Leu) consists of 1) removing amino-protecting groups, 2) transpeptidase reaction, 3) the cutting of a peptide chain, 4) cyclization of the peptide chain. The cyclic peptide compounds which are provided with the residue fragment of Val-Sta-Leu- and used as immunosuppressive agents and have a high yield and a high purity can be obtained, and the immunosuppressive activity of the cyclic peptide compounds is higher. Through the experiments of the retarding effect of A3HS1 towards the delayed hypersensitivity of mice, the influence of phagocytic function of macrophages, and the retarding effect of the proliferation of lymphocytes, the A3HS1 shows a stronger immunosuppressive effect than HS-1, which reaches or surpasses the immunosuppressive of the positive contrast (cyclosporine).

Description

technical field The invention relates to a peptide compound, specifically a cyclic peptide with a -Val-Sta-Leu- residue fragment that can be used as an immunosuppressant and a synthesis process. Background technique Hymenistatin-1 (HS-1) is a cyclic octapeptide isolated from the Pacific hymeniacidon sponge by researchers such as Pettit (Pettit G.R., Clewlow P.W., Dufresne C., et al. Isolation and structure of the cyclic peptide hymenistatin I . Can. J. Chem. 1990, 68: 708-711.). The sequence of the peptide chain is: cyclo(Pro-Pro-Tyr-Val-Pro-Leu-Ile-Ile). For the convenience and accuracy of discussion, the amino acid residues are numbered, that is, HS-1 is expressed as (Ile 1 -Ile 2 -Pro 3 -Pro 4 -Tyr 5 -Val 6 -Pro 7 -Leu 8 ). It has been reported that HS-1 has an inhibitory effect on cell growth in the study of P388 in mouse lymphoblastic non-leukemic leukemia, but the results have not been fully confirmed in subsequent studies. Researchers such as Siemion reve...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K1/02C07K1/20A61P37/06
CPCY02P20/55
Inventor 李湘徐琪
Owner CHINESE PEPTIDE CO
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