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Synthetic peptide containing glycine, L-cysteine and L-phenylalanine and application of synthetic peptide

A technology for synthesizing peptides and amino acids, which is applied in the field of biomedicine, can solve the problems of excessive dosage, serious side effects, and limited clinical application, and achieve the effects of small side effects, improvement of oxidative stress damage, and improvement of cognitive dysfunction and dementia

Active Publication Date: 2016-12-07
WUHAN HONGYUE MEDICAL SCI INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although both glycine and cysteine ​​have obvious brain protective effects, the current treatment plan is to administer glycine (800mg / kg) or cysteine ​​(500mg / kg) alone peripherally, and the dose is too large, resulting in serious side effects , limiting their clinical application

Method used

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  • Synthetic peptide containing glycine, L-cysteine and L-phenylalanine and application of synthetic peptide
  • Synthetic peptide containing glycine, L-cysteine and L-phenylalanine and application of synthetic peptide
  • Synthetic peptide containing glycine, L-cysteine and L-phenylalanine and application of synthetic peptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] [Example 1] This patent takes glycine-L-cysteine-L-phenylalanine tripeptide (GCF) as an example to illustrate the preparation process of the solid-phase synthetic peptide as follows:

[0060] 1. Synthesis of Complex I Fmoc-L-Phe-resin:

[0061] The tripeptide of this patent uses the method of solid-phase synthesis, weighs 10.7g of 2-chlorotrityl chloride resin (2-Chlorotrityl Chloride Resin) with a degree of substitution of 0.4mmol / g, puts the resin into a polypeptide reaction tube, and adds Dichloromethane (DCM) 160.5ml, shaken for 30 minutes; filter the DCM solvent through sand core, add 12mmol of Fmoc-L-Phe-OH amino acid, then add 40mmol of N,N-diisopropylethylamine (DIEA ), and finally add a small amount of dimethylformamide (DMF) to dissolve, shake for 1h. Alternately wash 6 times with DMF and DCM. Add 160.5ml of 20% piperidine (piperidine is dissolved in DMF solution), remove the piperidine after 5 minutes, add 160.5ml of 20% piperidine again, remove the piperid...

Embodiment 2

[0078] [Example 2] Cytotoxicity test of the patent small peptide on primary cortical neurons

[0079] In this example, the primary cortical neurons cultured for 10 days were used as the experimental object, the neurons were treated with different concentrations of GCF, and the cell viability was evaluated by cck8, so as to judge the cytotoxicity of GCF, and the phosphorylation level of Akt was used to illustrate Whether GCF has a certain degree of protective effect on nerve cells. It was found that when GCF>=800μM, it has obvious protective effect. In order to determine whether the small peptides of this patent also have a protective effect on the brain, we established an isolated glucose-oxygen deprivation (OGD) model of cortical neurons. Under the condition of OGD injury, the neurons were treated with 500 μM of each small peptide, and evaluated by cck8 The viability of the cells can be used to determine whether each small peptide has a protective effect on neurons. The sma...

Embodiment 3

[0103] [Example 3] Establish a rat cerebral ischemia model, inject fluorescently labeled small peptides intravenously, and observe the ability of small peptides to penetrate the blood-brain barrier as a whole

[0104] 1. The main reagents and instruments of the experiment

[0105]FITC, Wuhan Minghao Biotechnology Co., Ltd.; FITC-GC and FITC-GCF, Wuhan Minghao Biotechnology Co., Ltd.; OCT glue, Beijing Zhongshan Jinqiao Biotechnology Co., Ltd.; pathological tissue slicer, Leitz, Germany, type 1512; Fluorescence microscope, Ningbo Sunny Instrument Co., Ltd.; paraformaldehyde, Sinopharm Chemical Reagent Co., Ltd.

[0106] 2. Experimental principle

[0107] FITC (fluorescein isothiocyanate): It is yellow or orange-yellow crystalline powder with a molecular weight of 389.4, a maximum absorption wavelength of 490-495nm, and a maximum emission wavelength of 520-530nm, showing bright yellow-green fluorescence. The broadest fluorescein.

[0108] FITC-GCF: GCF is fluorescently labele...

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Abstract

The invention belongs to the technical field of biological medicine, and particularly relates to a synthetic peptide and application of the synthetic peptide in preparation of drugs for treating cerebral injuries. An amino acid sequence of the synthetic peptide is X1-(Gly-L-Cys)n-X2-X3, wherein, X1 is a free position or L-Phe, X2 is a free position or Gly, X3 is a free position or L-Phe, X1 and X3 cannot be free positions simultaneously, and n is smaller than or equal to 8. It is shown through animal experiments that the synthetic peptide can pass through a blood brain barrier to reach the brain in an intravenous administration mode under an extremely low dose and is rapidly hydrolyzed, and then free glycine and cysteine are generated to play a brain protective role. The invention provides a new idea and a new small peptide for the drugs for treating the cerebral injuries.

Description

[0001] Cross References to Related Applications [0002] This application claims priority from Chinese application 201610080163.4, filed February 5, 2016, which is incorporated herein in its entirety by reference. technical field [0003] The invention belongs to the technical field of biomedicine, and in particular relates to a synthetic peptide and its application in preparing medicine for treating brain injury. Background technique [0004] Stroke is a sudden onset cerebral blood circulation disorder, clinically manifested as symptoms and signs of one-time or permanent brain dysfunction. Stroke is divided into ischemic stroke and hemorrhagic stroke according to its nature. Stroke is a refractory disease that seriously endangers human life and safety. It has the characteristics of high morbidity, high disability and high mortality. In 2008, in the ranking of causes of death announced by the Ministry of Health of my country, stroke ranked No. 1 among cities. Three, the sec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K7/08C07K5/103C07K5/107C07K5/087C07K5/083A61K38/06A61K38/07A61K38/08A61K38/10A61P9/10A61P25/00A61P25/16A61P25/28
CPCA61K38/00C07K5/0806C07K5/0812C07K5/1008C07K5/1016C07K7/06C07K7/08
Inventor 万芪陈娟庄杨张娅万沙
Owner WUHAN HONGYUE MEDICAL SCI INC
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