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Cyclic peptides with -Pro-Sta-Tyr- residue fragment as immunity inhibitor and synthesis process thereof

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

Active Publication Date: 2011-05-04
CHINESE PEPTIDE CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] 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 peptides with -Pro-Sta-Tyr- residue fragment as immunity inhibitor and synthesis process thereof
  • Cyclic peptides with -Pro-Sta-Tyr- residue fragment as immunity inhibitor and synthesis process thereof
  • Cyclic peptides with -Pro-Sta-Tyr- residue fragment as immunity inhibitor and synthesis process thereof

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Embodiment Construction

[0027] The technical solutions of the present invention will be further specifically described below through examples.

[0028] 1 synthesis part

[0029] 1.1 Instruments and reagents

[0030] Peptide synthesizer (ABI 433, American ABI company), semi-preparative high performance liquid chromatography (WatersDelta Prep 4000, American Waters company), analytical high performance liquid chromatography (Agilent 1100, American Agilent company), freeze dryer ( Christ Alpha, German CHRIST company), ion trap mass spectrometer (LCQ Deca, American Thermo-Finnigan company), ultraviolet spectrophotometer (BeckmanDU7400, American Beckman company), C18 reversed-phase analysis column (Waters XTerra, 3.5um, 4.6×150mm).

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Abstract

The invention relates to cyclic peptide used as immunosuppressant and carried with -Pro-Sta-Tyr- residue fragment as well as ring (Ile-Ile-Pro-Sta-Tyr-Val-Pro-Leu). The synthesis process of the invention is as follows: (1) amino protecting group is removed; (2) synthesized peptide is completed; (3) peptide chain cutting is carried out; (4) peptide chain cyclization is completed. Therefore, a cyclic peptide compound, which has high yield, high purity and -Pro-Sta-Tyr- residue fragment and can be used as immunosuppressant, can be obtained; moreover, the compound has higher immunosuppression activity. The experiments on the inhibition of A2HS1 on mouse delayed hypersensitivity, the influence on the phagocytic capability of macrophage and the inhibition on lymphopoiesis show that the A2HS1 represents stronger natural immunosuppression than HS-1 and reaches or exceeds positive contrast (cyclosporin) immunosuppression.

Description

technical field [0001] The invention relates to a peptide compound, specifically a cyclic peptide with a -Pro-Sta-Tyr- residue fragment that can be used as an immunosuppressant and a synthesis process. Background technique [0002] 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 ). [0003] 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. [0004] ...

Claims

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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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