A kind of antitumor active peptide, synthesis method and application

A technology of anti-tumor activity and synthesis method, which is applied in the field of synthesis and anti-tumor active peptides, can solve the problems of poor anti-tumor activity, achieve excellent anti-tumor activity, reduce steric hindrance, and improve cyclization efficiency

Active Publication Date: 2022-03-08
ANHUI POLYTECHNIC UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the defect of poor antitumor activity of the cyclic peptide Samoamide A naturally extracted from marine algae, the present invention provides a method to replace two phenylalanines in the original Samoamide A cyclic peptide by using two D-phenylalanines. acid, to obtain Samoamide C, a derivative based on Samoamide A. Under the same application concentration, Samoamide C has significantly improved the inhibition rate of DPP-4 enzyme activity and the cytotoxicity of tumor cells, reflecting more excellent anti-tumor activity.

Method used

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  • A kind of antitumor active peptide, synthesis method and application
  • A kind of antitumor active peptide, synthesis method and application
  • A kind of antitumor active peptide, synthesis method and application

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Embodiment 1

[0060] The synthesis of the tumor suppressor active peptide C in this embodiment specifically includes the following steps:

[0061] (1) Coupling reaction between resin and amino acid

[0062] Weigh 2.00 g of 2-chlorotrityl chloride resin and put it into the sand core tube for polypeptide synthesis. Add DMF and use a rotary vane vacuum pump to blow and wash for 5-10 seconds, then use a circulating water-type multi-purpose vacuum pump to filter the liquid, add DCM to soak the resin and blow for 2-3 minutes to fully expand and then filter. Weigh 451.4 mg of Fmoc-Val-OH and put it into a sand core tube, add DCM as a reaction solvent, add 1 mL of DIEA dropwise as a condensation reagent, blow the reaction at room temperature for 30 minutes, pump out the liquid, add DMF to wash 4 times and filter with suction. Add DCM again, add dropwise 4mL of anhydrous methanol and 4mL DIEA to react for 30min, and cap the unreacted sites of the resin. After the reaction was finished, filter with...

Embodiment 2

[0082] This embodiment is an antitumor activity verification experiment for Samoamide A and Samoamide C, including the following steps:

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

[0084] The imported DPP-4 enzyme inhibitor sitagliptin and the experimental method provided were used to verify the inhibitory effect of several derivatives on DPP-4 enzyme activity. Take an opaque 96-well black microtiter plate, and drop 1 μL of DPP-4 enzyme solution and 49 μL of test buffer into each control. Then set up each group of experiments:

[0085] Group 1-blank group: without adding any substance;

[0086] Group 2 - sample group to be tested: add 25 μL of peptide solution with DMSO as solvent, the concentration is 100 μg / mL, and test the experimental groups of Samoamide A and Samoamide C peptide solutions respectively;

[0087] Group 3-inhibitor comparison group: pipette 2 μL of the sitagliptin inhibitor mother solution provided in the kit, add buffer to dilute it 100 tim...

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Abstract

The invention belongs to the field of biotechnology, and discloses an anti-tumor active peptide, a synthesis method and an application. The structure of the active peptide is: Cyclo-(Leu-Pro-Pro-(D-Phe)-Ile-Pro-(D -Phe)-Val). The synthesis method comprises the following steps: 1) using resin and amino acid for coupling reaction, so that linear peptide is coupled on the resin; 2) adding cutting solution to the resin for reaction, collecting the solution after reaction, adding DIEA dropwise to the solution Adjust the pH value to be neutral to obtain a crude product solution of the linear peptide; 3) add the crude product solution of the linear peptide dropwise into the cyclic peptide reaction system to synthesize the cyclic peptide. The present invention replaces the two phenylalanines in the original Samoamide A cyclic peptide by two D-phenylalanines, and obtains Samoamide C based on the derivative of Samoamide A through a suitable solid-phase synthesis method, and the prepared Samoamide C The inhibition rate of DPP-4 enzyme activity and the toxicity to tumor cells are significantly improved, reflecting more excellent anti-tumor activity.

Description

technical field [0001] The invention belongs to the field of biotechnology, and specifically relates to an anti-tumor active peptide, a synthesis method and an application. Background technique [0002] Peptide drugs are widely concerned because of their small molecular weight, high specificity, and low side effects. They are considered to be good drugs for treating malignant tumors. 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 solid-phase synthesis to improve the yield and simultaneously improve its activity, so that it can be more widely used. application. [0003] After searching, for the synthesis method of Samoamide A, related applications have been published in the prior ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K1/06C07K1/04A61K38/12A61P35/00
CPCC07K7/64A61P35/00A61K38/00
Inventor 陶玉贵陈刘旺李婉珍葛飞宋平朱龙宝张伟伟
Owner ANHUI POLYTECHNIC UNIV
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