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Peptide compound as well as preparation method and application thereof

A compound and target compound technology, applied in the field of peptide compounds and their preparation, can solve problems such as poor quality, achieve strong inhibitory activity and promote cell apoptosis

Active Publication Date: 2020-09-25
RENJI HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the neutral loss scan means that Q1 and Q3 perform a full scan at the same time, but the two always maintain a certain fixed mass difference. Only the neutral part lost in the collision cell Q2 meets this fixed mass difference. Ions can be detected

Method used

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  • Peptide compound as well as preparation method and application thereof
  • Peptide compound as well as preparation method and application thereof
  • Peptide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1 finds and extracts natural compound 1 (C from sponge) 45 h 61 N 11 o 8 )

[0064] From the mass spectrometry fragmentation mechanism of peptide compounds, it is found that the secondary fragment ions formed after the collision-induced dissociation of cyclic peptides are often caused by the loss of certain neutral molecular fragments. Most of these neutral molecules are the basic units of the cyclic peptide— - Each amino acid residue. According to this feature, the analysis of secondary MS found that the cyclic peptide containing kynurenine can be quickly searched through the parent ion with a poor mass of 190Da among the fragment ions. The crude fraction of the brown flat sponge Phakellia fusca (belonging to the class Demospongiae, order Halichondrid, family Axinellidae, genus Phakellia) collected from the waters near the Xisha Islands in China was scanned by neutral loss mass spectrometry , from which the precursor ion was found to be m / z884.48[M+H] ...

Embodiment 2

[0094] Embodiment 2 prepares compound 1 of the present invention by synthesis

[0095] Synthetic route of compound 1

[0096]

[0097] The synthesis steps are as follows:

[0098] Loading of the first amino acid into 2-CTC resin: 2-CTC resin (100 mg, loading: 1.0 mmol / g) was swelled in a disposable container (TORIVQ) with 2 mL of anhydrous DCM for 20 minutes. Fmoc-Pro-OH (2.0 equiv) and DIEA (4.0 equiv) in DCM were added and the reaction vessel was shaken on a vortex at room temperature for 1 hour. Add 200 µL of MeOH to the reaction mixture and spin the resin for 15 min. The resin was filtered and washed with anhydrous DCM (3 mL×5 times, 1 min / time), 1:1 DCM / MeOH (v / v) (3 mL×5 times, 1 min / time) and MeOH (3 mL×2 times, 1 min / time) times) washing.

[0099] Fmoc deprotection: at room temperature, use 3 mL of 20% piperidine in DMF solution for Fmoc deprotection for 20 minutes, and then wash the resin with DMF (3 mL×2 times, 1 minute / time).

[0100] Peptide coupling: Gentl...

Embodiment 3

[0107] Embodiment 3 The in vitro activity experiment of compound 1 of the present invention

[0108] Cytotoxic activity test: the compound 1 of the present invention was tested for its cytotoxic activity against six tumor cell lines (MCF-7, HeLa, NCI-H460, SW480, PC9 and HepG2) and one normal cell line (H9C2). The sample was dissolved in DMSO and stored at low temperature. The concentration of DMSO in the final system was controlled within the range that did not affect the detection activity, and the working concentration was 1-100 μg / mL by doubling dilution. Take the cells in the logarithmic growth phase and make a single cell suspension 1×10 6 per mL, the suspension was added to a 96-well plate, and 100 μL was added to each well. at 5% CO 2 After culturing in a 37°C incubator for 24 hours, each concentration of the test drug was added to make the final concentrations respectively 100, 50, 25, 12.5, and 6.25 μg / mL. Three replicate holes were set up for each sample, and the ...

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Abstract

The invention belongs to the technical field of medicinal chemistry. The invention discloses linear peptide or cyclic peptide with the tumor cell inhibition activity. The linear peptide or cyclic peptide contains condensation fragments of kynurenine and arginine. A mass spectrum rapid positioning method for selectively identifying a cyclic peptide compound containing the kynurenine in complex extract is further used for separating and obtaining a new cyclic peptide compound with the antitumor activity from phakellia fusca thiele; and full synthesis of the compound is realized by applying solid-phase synthesis, liquid-phase cyclization and ozonation strategies in the final stage.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a peptide compound and its preparation method and application. Background technique [0002] Sponges are the oldest and simplest multicellular animals with an evolutionary history of more than 500 million years. They rely on filtered seawater to feed, lack real tissues, cannot move and lack physical defenses. In the harsh competitive environment of the ocean, sponges defend against foreign biological attacks by producing active secondary metabolites. Sponge is one of the most prolific and important sources of new marine compounds. Since the study of marine natural products began in the 1960s, active substances with novel structures found in sponges account for about one-third of marine natural products every year. At present, a total of 49 active substances derived from marine sources have been approved for marketing or entered into clinical practice at home and abro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/64C07K7/06C07K5/12C07K1/16C07K1/20C07K1/14C07K1/04C07K1/02C07K1/06A61K38/12A61K38/08A61K38/07A61P35/00
CPCA61K38/00A61P35/00C07K5/126C07K7/06C07K7/64Y02P20/55
Inventor 林厚文王淑萍吴莹孙凡刘丽云
Owner RENJI HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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