Modified polypeptide based on marine cyclic peptide Samoamide A, synthetic method and application

A marine cyclic peptide and a synthesis method technology, applied in the biological field, can solve problems such as poor anti-tumor activity, and achieve the effects of excellent anti-tumor activity, reducing steric hindrance, and improving tumor cytotoxicity

Active Publication Date: 2020-10-16
ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the defect of poor antitumor activity of a cyclic peptide Samoamide A naturally extracted from marine algae, the present invention provides a method that uses two 4-Br-Phes to replace two phenylal

Method used

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  • Modified polypeptide based on marine cyclic peptide Samoamide A, synthetic method and application
  • Modified polypeptide based on marine cyclic peptide Samoamide A, synthetic method and application
  • Modified polypeptide based on marine cyclic peptide Samoamide A, synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0058] Example 1

[0059] The synthesis of the tumor suppressor peptide B of this embodiment specifically includes the following steps:

[0060] (1) Coupling reaction between resin and amino acid

[0061] Weigh 2.00 g of 2-chlorotrityl chloride resin and put it into the peptide synthetic sand core tube. Add DMF and use a rotary vane vacuum pump to blow in air for 5-10 seconds, then use a circulating water multi-purpose vacuum pump to filter the clean liquid, add DCM soaking resin and blow for 2 to 3 minutes to fully expand and then filter. Weigh 451.4 mg of Fmoc-Val-OH and put it into the sand core tube, add DCM as the reaction solvent, drop 1 mL of DIEA as the condensation reagent, blow the reaction at room temperature for 30 minutes, then pump out the liquid, add DMF to wash 4 times and filter with suction. DCM was added again, 4 mL of anhydrous methanol and 4 mL of DIEA were added dropwise to react for 30 minutes, and the unreacted sites of the resin were capped. After the reac...

Example Embodiment

[0081] Example 2

[0082] This example is an anti-tumor activity verification experiment for Samoamide A and Samoamide B, which includes the following steps:

[0083] (1) DPP-4 enzyme activity inhibition experiment

[0084] Use imported DPP-4 enzyme inhibitor sitagliptin and the experimental methods provided to verify the inhibitory effect of several derivatives on DPP-4 enzyme activity. Take an opaque 96-well black ELISA plate, and add 1μL DPP-4 enzyme solution and 49μL test buffer to each control.

[0085] Then set up each set of experiments:

[0086] Group 1-Blank group: do not add any substance;

[0087] Group 2-sample group to be tested: add 25 μL of the peptide solution with DMSO as the solvent, the concentration is 100 μg / mL, and test the experimental group of the peptide solution of Samoamide A and Samoamide B respectively;

[0088] Group 3-inhibitor comparison group: draw 2μL of the sitagliptin inhibitor mother solution provided in the kit, add buffer to dilute it by 100 times, ...

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Abstract

The invention belongs to the technical field of biology and discloses a modified polypeptide based on marine cyclic peptide Samoamide A, a synthetic method and application. The structure of the activepeptide is as follows: cyclic-(Leu-Pro-(4-Br-Phe)-Ile-Pro-(4-Br-Phe)-Val). The synthetic method comprises following steps: 1), resin and amino acid are subjected to a coupling reaction, and the resinis coupled with a linear peptide; 2), cutting fluid is added to the resin for a reaction, a solution obtained after the reaction is collected, DIEA is dropwise added to the solution to regulate pH value to be neutral, and a crude product solution of the linear peptide is obtained; and 3), the crude product solution of the linear peptide is dropwise added to a cyclic peptide reaction system to synthesize the cyclic peptide. According to the invention, two Br-phenylalanines replace two phenylalanines in original cyclic peptide Samoamide A, a derivative Samoamide B based on the Samoamide A is obtained with an appropriate solid-phase synthesis method, DPP-4 enzyme activity inhibition ratio and cytotoxicity to tumor cells of the prepared Samoamide B are remarkably increased, and Samoamide B shows excellent antitumor activity.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a modified polypeptide based on the marine cyclic peptide Samoamide A, a synthesis method and an application. Background technique [0002] Peptide compounds have become an important research direction of anti-tumor chemical drugs due to their advantages of low toxicity, clear target specificity and small molecular weight. In particular, cyclic peptide compounds have attracted more and more attention from researchers because of their long half-life in vivo, relatively stable structure, and strong cell membrane penetration. [0003] Samoamide A[-(Leu-Pro-Pro-Phe-Ile-Pro-Phe-Val)-] is a cyclic peptide naturally extracted from marine algae, and has a good toxic effect on tumor cells. However, the natural extraction of Samoamide A has low extraction yield and poor activity, and cannot be produced and applied on a large scale. Therefore, it is necessary to invent a method for...

Claims

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Application Information

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IPC IPC(8): C07K7/64C07K1/06C07K1/04A61K38/12A61P35/00
CPCC07K7/64A61P35/00A61K38/00
Inventor 葛飞陈刘旺李婉珍陶玉贵宋平朱龙宝张伟伟
Owner ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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