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Cyclo-pentapeptide with antineoplastic activity

A technology of cyclic pentapeptides and anti-tumor drugs, which is applied in the field of cyclic pentapeptides, can solve the problems of extracting cyclic peptides that have not yet been seen, and achieve the effects of strong anti-tumor activity, low production cost, and simple preparation process

Inactive Publication Date: 2008-09-24
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Filamentous Lactobacillus belongs to the Rhodophyta Lactobacillus genus. There are few research reports on the genus Lactobacillus at home and abroad, and there is no report on the extraction of cyclic peptides from Lactobacillus.

Method used

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  • Cyclo-pentapeptide with antineoplastic activity
  • Cyclo-pentapeptide with antineoplastic activity
  • Cyclo-pentapeptide with antineoplastic activity

Examples

Experimental program
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Effect test

Embodiment 1

[0027] The preparation of embodiment 1 cyclic pentapeptide

[0028] The preparation method of cyclic pentapeptide, its concrete steps are as follows:

[0029] (1) Soak and extract Filamentous Lactobacillus in ethanol at a temperature of 20°C, and concentrate the soaked extract under reduced pressure after 45 days;

[0030] (2) After the concentrated extract was extracted with ethyl acetate solution, concentrated under reduced pressure at 20°C to obtain the crude extract;

[0031] (3) The above crude extract is subjected to silica gel chromatography to obtain the crude cyclopentapeptide, and then recrystallized from methanol to obtain the cyclopentapeptide monomer.

[0032] The cyclic pentapeptide is a white needle-like crystal with a molecular formula of C 32 h 59 N 5 o 5 ,[M+H] + m / z: 594.4, mp: 208-210°C, [ α ] D 25 = - 130 ...

Embodiment 2

[0033] Embodiment 2 in vitro antitumor activity test

[0034] Adopt tetramethyl azolium salt microenzyme reaction colorimetry (MTT method), the cyclic pentapeptide (I) that embodiment 1 obtains and human liver cancer cell line HepG2, human breast cancer cell line MCF-7, human liver cancer cell line Strain BEL-7402, human colon cancer cell line LOVO, human nasopharyngeal carcinoma cell line CNE and human lung cancer cell line PC84045 were treated for 72 hours respectively. The results are shown in Table 2.

[0035] Table 2 cyclic pentapeptide (I) to the half maximal effective concentration (IC) of tumor cells 50 )

[0036]

[0037] Example 3 Effect test of cyclic pentapeptide on cycle of BEL-7402 liver cancer cells

[0038] Adopt propidium iodide (PI) staining method, after cyclic pentapeptide of different concentration (the cyclopentapeptide that embodiment 1 prepares) acts on BEL-7402 liver cancer cell 48 hours, flow cytometer measures cell cycle result as shown in Table...

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Abstract

The present invention discloses a cyclic pentapeptide with anti-tumour activity, which is cyclic (leucyl-N-methylleucyl-leucyl-leucyl-N-methylleucyl) and the constitutional formula of which is shown in the formula (I). The cyclic pentapeptide of the present invention is separated from galaxaura filamentosa in the South China Sea, and in vitro experiments show that the cyclic pentapeptide has strong inhibiting effect on human hepatoma cell lines (HepG2), human hepatoma cell lines (BEL-7402), human mammary cancer cell lines (MCF-7), human colon cancer cell lines (LOVO), human lung cancer cell lines (PC84045) and human nasopharyngeal cancer (CNE) and can keep the mitotic cycle of BEL-7402 hepatoma cells in G2 / M phase. The present invention provides a pilot compound for the research and the development of new anti-tumour drugs and is valuable for the exploitation of the marine pharmaceutical resources of China.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a cyclic pentapeptide with antitumor activity extracted from marine organisms seaweed. Background technique [0002] As the most characteristic class of peptide compounds, cyclic peptides are stronger than linear peptide compounds in terms of receptor selectivity and in vivo metabolic stability due to their relatively stable conformation. Cyclic peptides are effective in antifungal and Many aspects such as killing tumor cells have shown natural advantages. [0003] In the past, cyclic peptides in patents were mostly derived from terrestrial animals, plants, and microorganisms, with limited resources and a single type, such as CN99815515.2, CN02114663.2, etc. Marine organisms have become a huge treasure house of biologically active substances due to the diversity of species and the diversity of chemical structures of metabolites. Marine organisms are different from terrestrial ...

Claims

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Application Information

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IPC IPC(8): C07K7/64A61K38/12A61P35/00
Inventor 徐石海许文杰
Owner JINAN UNIVERSITY
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