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Anti-tumor cyclic peptide and its preparation method and application

An anti-tumor and cyclic peptide technology, applied in the field of cyclic peptides, can solve the problems of how to improve the anti-tumor effect of the cyclic peptide SamoamideA, and achieve excellent anti-tumor effects, high yield and wide application prospects

Active Publication Date: 2022-05-17
ANHUI POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, research on the functional aspects of the cyclic peptide Samoamide A is on the rise at home and abroad, but the specific transformation direction of the cyclic peptide Samoamide A is still in the initial stage of exploration, and it has not been able to explore how to improve the anti-tumor effect of the cyclic peptide Samoamide A

Method used

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  • Anti-tumor cyclic peptide and its preparation method and application
  • Anti-tumor cyclic peptide and its preparation method and application
  • Anti-tumor cyclic peptide and its preparation method and application

Examples

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preparation example 1

[0076] Cutting fluid: prepare 95% trifluoroacetic acid.

Embodiment 1

[0077] Embodiment 1 (as figure 1 shown)

[0078] 1) Soak 1000mg of 2-chlorotrityl chloride resin (substitution degree 1.03mmol / g) with 15mL of DCM at 30-35°C for 0.5h, then remove the DCM.

[0079] Ligation reaction of a single amino acid: Before connecting the first amino acid, weigh 311.3 mg of Fmoc-Ala-OH amino acid, soak it in 977 μL of DIPEA and 10 mL of DCM for 1 hour to activate, then connect the resin and react at 30-35°C for 1-1.5 h to obtain compound 1; then use 15mL of 20% methanol volume ratio dichloromethane solution, react at 30-35°C for 30min, block the sites on the resin that do not participate in the reaction, after the reaction, wash with DCM and DMF respectively for 3 Repeat, pump out the washing liquid. Add 15 mL of 25% piperidine volume ratio DMF solution into the reaction tube, react for 30 min, remove the Fmoc protecting group, after the reaction, wash with DCM and DMF for 5 times respectively, and remove the washing solution.

[0080] Repeat the abov...

Embodiment 2

[0084] 1) Soak 1000mg of 2-chlorotrityl chloride resin (substitution degree 1.03mmol / g) with 15mL of DCM at 30-35°C for 0.5h, then remove the DCM.

[0085] Ligation reaction of a single amino acid: Before connecting the first amino acid, weigh 387.0 mg of Fmoc-Phe-OH amino acid, soak it in 977 μL of DIPEA and 10 mL of DCM for 1 hour to activate, then connect the resin and react at 30-35°C for 1-1.5 h to obtain Fmoc-Phe-2-chlorotrityl chloride resin; then use 15mL of 20% methanol volume ratio dichloromethane solution, react for 30min at 30-35°C, and block the sites that do not participate in the reaction on the resin, After the reaction, wash with DCM and DMF three times respectively, and remove the washing solution. Add 15 mL of 25% piperidine volume ratio DMF solution into the reaction tube, react for 30 min, remove the Fmoc protecting group, after the reaction, wash with DCM and DMF for 5 times respectively, and remove the washing solution.

[0086] Repeat the above steps o...

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PUM

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Abstract

The invention discloses an anti-tumor cyclic peptide and its preparation method and application. The structure of the tumor cyclic peptide is as follows: formula (I-1), formula (I-2), formula (I-3), formula (I-4 ), formula (I‑5), formula (I‑6), formula (I‑7), formula (I‑8); the anti-tumor cyclic peptide has a more excellent anti-tumor effect, and at the same time The preparation method has the advantages of simple procedure and high yield, so that the anti-tumor cyclic peptide can have wide application prospects.

Description

technical field [0001] The present invention relates to cyclic peptides, in particular to an anti-tumor cyclic peptide and its preparation method and application. Background technique [0002] The cyclic peptide Samoamide A is a polypeptide extracted from the marine cyanobacteria Symploca spp, an octacyclic peptide composed of Phe-Pro-Ile-Phe-Pro-Pro-Leu-Val (05Jan 2017,80(3):625 -633), Samoamide A inhibits the enzyme dipeptidyl peptidase (CD26, DPP4) at the allosteric binding site of cancer cells, which was shown to be effective in several human cancer cell lines in conventional cell culture and domain inhibition bioassays has in vitro cytotoxic activity. [0003] At present, research on the functional aspects of the cyclic peptide Samoamide A is on the rise at home and abroad, but the specific transformation direction of the cyclic peptide Samoamide A is still in the initial stage of exploration, and it has not been able to explore how to improve the anti-tumor effect of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K1/02C07K1/06A61K38/12A61P35/00
CPCA61P35/00C07K7/64A61K38/00Y02P20/55
Inventor 葛飞张驰陶玉贵张旭光孙良玉朱龙宝
Owner ANHUI POLYTECHNIC UNIV