Anticancer peptide containing poly-L-histidine as well as preparation and application thereof

A technology of polyhistidine and histidine, which is applied in the field of anti-tumor polypeptide drugs, can solve the problems of increased permeability, decreased activity of cancer cells, death, etc., and achieves the effect of convenient artificial synthesis and simple structure

Pending Publication Date: 2017-05-31
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These peptides increase the permeability of the cell membrane by inserting and cleaving it, leading to the reduction of cancer cell activity and death

Method used

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  • Anticancer peptide containing poly-L-histidine as well as preparation and application thereof
  • Anticancer peptide containing poly-L-histidine as well as preparation and application thereof
  • Anticancer peptide containing poly-L-histidine as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0058] The preparation of the anticancer polypeptide 1 comprises the following steps:

[0059] (1) Add Rink amide resin (309mg, 0.810mmol / g, 0.25mmol, 1equiv) to DMF / DCM (v / v=1 / 1; 10mL) to swell for 3h, wash the resin with DMF, and then use piperidine / DMF ( v / v=1 / 4; 10mL) to remove the Fmoc protecting group, react for 20 minutes; wash the resin with DMF, put Fmoc-His(Trt)-OH (0.75mmol, 3.0equiv) in the reaction flask, add organic Alkali (2.5mmol, 10equiv) and condensing agent (0.75mmol, 3.0equiv), after reacting in DMF solution for 3 hours, remove Fmoc protecting group again, obtain the resin coupled with histidine;

[0060] (2) Put the Rink amide resin reacted with the first histidine and Fmoc-His(Trt)-OH (0.75mmol, 3.0equiv) in a reaction flask, add organic base (2.5mmol, 10equiv) and condensation The mixture (0.75mmol, 3.0equiv) was reacted in DMF solution for 3 hours at room temperature. After the reaction is complete, let stand, drain the DMF, wash the resin with DMF, t...

preparation Embodiment 2

[0069] The preparation of the anticancer polypeptide 2 comprises the following steps:

[0070] (1) Add Rink amide resin (309mg, 0.810mmol / g, 0.25mmol, 1equiv) to DMF / DCM (v / v=1 / 1; 10mL) to swell for 3h, wash the resin with DMF, and then use piperidine / DMF ( v / v=1 / 4; 10mL) to remove the Fmoc protecting group, react for 20 minutes; wash the resin with DMF, put Fmoc-His(Trt)-OH (0.75mmol, 3.0equiv) in the reaction flask, add organic Alkali (2.5mmol, 10equiv) and condensing agent (0.75mmol, 3.0equiv), after reacting in DMF solution for 3 hours, remove Fmoc protecting group again, obtain the resin coupled with histidine;

[0071] (2) Put the Rink amide resin reacted with the first histidine and Fmoc-His(Trt)-OH (0.75mmol, 3.0equiv) in a reaction flask, add organic base (2.5mmol, 10equiv) and condensation The mixture (0.75mmol, 3.0equiv) was reacted in DMF solution for 3 hours at room temperature. After the reaction is complete, let stand, drain the DMF, wash the resin with DMF, t...

preparation Embodiment 3

[0080] The preparation of the anticancer polypeptide 3 comprises the following steps:

[0081] (1) Add Rink amide resin (309mg, 0.810mmol / g, 0.25mmol, 1equiv) to DMF / DCM (v / v=1 / 1; 10mL) to swell for 3h, wash the resin with DMF, and then use piperidine / DMF ( v / v=1 / 4; 10mL) to remove the Fmoc protecting group, and reacted for 20 minutes; the resin was washed with DMF, and the aminododecanoic acid protected by Fmoc was placed in a reaction flask, and an organic base (2.5mmol, 10equiv) was added and Condensing agent (0.75mmol, 3.0equiv), after reacting in DMF solution for 3 hours, remove Fmoc protecting group again, obtain the resin coupled with aminododecanoic acid;

[0082] (2) Place the Rink amide resin and Fmoc-His(Trt)-OH (0.75mmol, 3.0equiv) in the reaction flask after reacting with aminododecanoic acid, add organic base (2.5mmol, 10equiv) and condensing agent ( 0.75mmol, 3.0equiv), in DMF solution, reacted at room temperature for 3 hours. After the reaction is complete, l...

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Abstract

The invention discloses an anticancer peptide containing poly-L-histidine as well as preparation and application thereof and belongs to the technical field of development and application of antitumor drugs. An amino acid sequence of the poly-L-histidine comprises a plurality of histidines; the poly-L-histidine has efficient antitumor activity. Through the adoption of a polypeptide solid phase synthesis technique, a series of peptides which are rich in histidine and have membrane cracking activity and antitumor activity are built; the peptides have effects of killing cancer cells and is especially capable of killing ovarian cancer SKOV-3 cells under the acid condition with high selectivity; cytotoxicity experiments of in-vitro ovarian cancer SKOV-3 cells, lung cancer A549 cells and breast cancer MCF-7 cells and the tumor-inhibiting experiment of mouse in-vivo ovarian cancer SKOV-3 tumor show that the poly-L-histidine peptide has excellent effects of treating ovarian cancer, lung cancer and breast cancer.

Description

technical field [0001] The invention relates to the field of anti-tumor polypeptide drugs, in particular to an anti-cancer polypeptide containing polyhistidine and its preparation and application. Background technique [0002] Malignant tumors seriously threaten human health and life. Among them, ovarian cancer is a common gynecological cancer. Its incidence rate ranks third after breast cancer and uterine body cancer. women's lives. Most of the current anti-tumor drugs have disadvantages such as low selectivity, strong side effects, and easy drug resistance. There is an urgent need to research and develop new anti-tumor drugs. [0003] Tumor drug resistance has always been a major obstacle to cancer treatment. High-efficiency anti-cancer polypeptide, as a candidate drug that directly and powerfully destroys tumor cells, is attracting more and more attention due to its special mechanism of action, which is not prone to tumor drug resistance. The development of anti-tumor ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/04A61K38/08A61P35/00
CPCC07K7/06A61K38/00Y02P20/55
Inventor 吴君臣姚德帆王坤艳罗深圳朱晓敏周于人赵朋田禾
Owner EAST CHINA UNIV OF SCI & TECH
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