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Open-loop rubiaceae-type cyclopeptide, pharmaceutical composition taking open-loop rubiaceae-type cyclopeptide as active ingredient as well as preparation method and application of open-loop rubiaceae-type cyclopeptide

A technology of Rubiaceae and composition, which is applied in the field of ring-opening Rubiaceae type cyclic peptides, can solve problems such as insufficient extraction, and achieve the effects of good controllability and reproducibility, convenient operation, and low cost

Inactive Publication Date: 2015-08-12
CHINA PHARM UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its disadvantage is that 70% methanol is insufficient for extraction as an extraction solvent

Method used

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  • Open-loop rubiaceae-type cyclopeptide, pharmaceutical composition taking open-loop rubiaceae-type cyclopeptide as active ingredient as well as preparation method and application of open-loop rubiaceae-type cyclopeptide
  • Open-loop rubiaceae-type cyclopeptide, pharmaceutical composition taking open-loop rubiaceae-type cyclopeptide as active ingredient as well as preparation method and application of open-loop rubiaceae-type cyclopeptide
  • Open-loop rubiaceae-type cyclopeptide, pharmaceutical composition taking open-loop rubiaceae-type cyclopeptide as active ingredient as well as preparation method and application of open-loop rubiaceae-type cyclopeptide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation and structural identification of the ring-opening Rubiaceae-type cyclic peptide compounds rubicordilin A(1), rubicordilin B(2) and rubicordilin C(3):

[0030] Take madder root and rhizome (200kg), after drying and crushing, reflux extraction with industrial methanol for 3 times (300L×3 times), 3 hours each time. The extract was concentrated under reduced pressure to obtain 29.2 kg of methanol extract. After the methanol extract was heated and suspended in water, the insoluble matter was filtered off, extracted 3 times with petroleum ether, ethyl acetate and n-butanol successively, and each part of the extract was concentrated under reduced pressure to obtain the petroleum ether part (2.6kg), ethyl acetate Ester fraction (4.0 kg), n-butanol fraction (3.0 kg) and water fraction (14.0 kg). The ethyl acetate fraction (4.0kg) was subjected to silica gel column chromatography and eluted with chloroform / methanol gradient (100:0, 20:1, 10:1, 9:1, 8:2, 7:3, 0:100 )...

Embodiment 2

[0054] The open-loop Rubiaceae type cyclic peptide compound rubicordilin A (1), rubicordilin B (2) and rubicordilin C (3) of the present invention are determined by SRB method in its human non-small cell lung cancer cell line (A549), human gastric cancer cell line (SGC- 7901) and human cervical cancer cells (HeLa), and found that the split-ring Rubiaceae type cyclic peptide compound has better cytotoxic activity. The experimental principles, methods and results are as follows:

[0055] Experimental principle: After co-cultivating the drug with the cells, the cell survival rate is measured. SRB is a water-soluble protein dye with a sulfonic acid group anion in the molecule, which can combine with basic amino acids of intracellular proteins under weakly acidic conditions. Dissolve SRB in cells with alkaline solution and measure its absorbance value. SRB The content of reflects the protein content in the cell, which reflects the cell viability.

[0056] Experimental method: Cel...

Embodiment 3

[0062] The open-loop Rubiaceae type cyclic peptide compounds rubicordilin A (1), rubicordilin B (2) and rubicordilin C (3) of the present invention are tested for their NF-κB signaling pathway inhibitory activity by the luciferase double reporter gene method, and it is found that the cyclic peptide compounds can Inhibits NF-κB pathway activity. The experimental principles, methods and results are as follows:

[0063] Experimental principle: The luciferase dual reporter gene system is often used to evaluate the effect of compounds on the activity of a certain signaling pathway. Luciferin emits fluorescence under the catalysis of luciferase, and the luminescence intensity is detected by a chemiluminescence microplate reader to reflect the activity of the pathway. strong and weak. NF-κB-dependent firefly luciferase plasmid (5×κB-luciferase) was transiently transfected in HEK 293T cells to specifically reflect the activity of NF-κB pathway, and Renilla luciferase plasmid (pTK-Ren...

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Abstract

The invention provides an open-loop rubiaceae-type cyclopeptide, a pharmaceutical composition taking the open-loop rubiaceae-type cyclopeptide as an active ingredient, an inhibitor taking the open-loop rubiaceae-type cyclopeptide as an NF-kappa b signal pathway, a preparation method of the open-loop rubiaceae-type cyclopeptide and an application of the open-loop rubiaceae-type cyclopeptide in a medicine used for treating and preventing inflammatory diseases and cancers related to abnormal activation of the NF-kappa b signal pathway. The open-loop rubiaceae-type cyclopeptide is a cyclic compound formed by condensing one D-alpha-aminopropionic acids, two L-alpha-aminopropionic acids and three substituted N-methyl-L-alpha-tyrosines by virtue of peptide bonds; and the open-loop rubiacea-type cyclopeptide with the structural formula (1-3) is an optimized NF-kappa b signal pathway inhibitor.

Description

Technical field: [0001] The present invention belongs to the technical field of medicines, and in particular relates to a class of ring-splitting Rubiaceae type cyclic peptides, which are used as NF-κB signaling pathway inhibitors, a pharmaceutical composition containing it as an active ingredient, its preparation method and its preparation method for treatment and treatment. Application of drugs to prevent inflammatory diseases and cancers related to NF-κB signaling pathway. Background technique: [0002] NF-κB signaling pathway is one of the classic and important signaling pathways in cells. Ranjan Sen and David Baltimore first discovered the nuclear transcription factor NF-κB in 1986. It is a protein factor that can specifically bind to the enhancer κB sequence of the immunoglobulin κ light chain gene in mature B cells. Studies have shown that NF-κB widely exists in eukaryotic cells, NF-κB exists in the cytoplasm in an inactive form by binding to the inhibitory protein I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K9/00C07K7/64C07K1/36C07K1/16A61K38/14A61K38/12A61P29/00A61P35/00
Inventor 谭宁华陈小强赵思蒙汪哲曾广智
Owner CHINA PHARM UNIV
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