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Mimetic peptide of erythropoietin, preparation method and applications thereof

A technology of mimicking peptides and medicinal salts, which is applied in the field of erythropoietin mimicking peptides, and can solve problems such as poor stability in vivo and inability to meet the conditions for drug production

Inactive Publication Date: 2013-12-18
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the half effective concentration (EC 50 ) The smallest is 200nM, which is much higher than the EC of EPO measured at the same time 50 (20pM), in addition, their in vivo stability is also poor, therefore, can not meet the requirements of drug

Method used

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  • Mimetic peptide of erythropoietin, preparation method and applications thereof
  • Mimetic peptide of erythropoietin, preparation method and applications thereof
  • Mimetic peptide of erythropoietin, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Example 1: Synthesis of SEQ-01 (see Table 1 for the structural sequence)

[0094] With 1.0g Rink-amide resin (0.25mmol) as a solid phase carrier, with Fmoc-Ala-OH, Fmoc-Arg(pbf)-OH, Fmoc-Cys(Trt)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Gly-OH, Fmoc-His(Trt)-OH, Fmoc-Ile-OH, Fmoc-Leu-OH, Fmoc-Lys(Boc)-OH, Fmoc-Met-OH, Fmoc-MeAla-OH, Fmoc- 1-Nal-OH, Fmoc-Phe-OH, Fmoc-Pro-OH, Fmoc-Ser(tBu)-OH, Fmoc-Sar-OH, Fmoc-Val-OH as raw material, HBTU-HOBt as condensing agent, according to SEQ According to the amino acid sequence of -01, the peptide resin was synthesized according to the standard Fmoc solid-phase peptide synthesis method. Use 20ml of trifluoroacetic acid: thioanisole: m-cresol: ethanedithiol: water (8.25:0.5:0.5:0.25:0.5, volume ratio) as the lysate, react at 0°C for 30 minutes, and at room temperature for 90 minutes, The peptide is deprotected and cleaved from the resin. Crude peptide dissolved in 20% DMSO / H 2 O solution is used as a medium for oxidation to form a disulfide ...

Embodiment 2

[0095] Example 2: Synthesis of SEQ-02 (see Table 1 for the structural sequence)

[0096] With 1.0g Rink-amide resin (0.25mmol) as a solid phase carrier, with Fmoc-Ala-OH, Fmoc-Arg(pbf)-OH, Fmoc-Cys(Trt)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Gly-OH, Fmoc-His(Trt)-OH, Fmoc-Ile-OH, Fmoc-Leu-OH, Fmoc-Lys(Boc)-OH, Fmoc-Met-OH, Fmoc-1-Nal-OH, Fmoc-Phe-OH, Fmoc-Pro-OH, Fmoc-Ser(tBu)-OH, Fmoc-Sar-OH, Fmoc-Tyr(OtBu)-OH, Fmoc-Val-OH as raw material, HBTU-HOBt as condensing agent According to the amino acid sequence of SEQ-02, according to the method of Example 1, SEQ-02 was obtained. The results of MALDI-Tof mass spectrometry are shown in Table 1.

Embodiment 3

[0097] Example 3: Synthesis of SEQ-03 (see Table 1 for the structural sequence)

[0098] With 1.0g Rink-amide resin (0.25mmol) as a solid phase carrier, with Fmoc-Ala-OH, Fmoc-Arg(pbf)-OH, Fmoc-Cys(Trt)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Gly-OH, Fmoc-His(Trt)-OH, Fmoc-Ile-OH, Fmoc-Leu-OH, Fmoc-Lys(Boc)-OH, Fmoc-MeAla-OH, Fmoc-Met-OH, Fmoc- 1-Nal-OH, Fmoc-Phe-OH, Fmoc-Pro-OH, Fmoc-Ser(tBu)-OH, Fmoc-Sar-OH, Fmoc-Tyr(OtBu)-OH, Fmoc-Val-OH as raw materials, HBTU-HOBt is a condensing agent. According to the amino acid sequence of SEQ-03, according to the method of Example 1, SEQ-03 was obtained. MALDI-Tof mass spectrometry analysis results Table 1.

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Abstract

The present invention relates to a mimetic peptide of erythropoietin represented by the Formula (I) and applications thereof. The mimetic peptide of erythropoietin or pharmaceutically-acceptable salts thereof can be used as alternatives of erythropoietin, and can be used in drugs for preventing and / or treating diseases and / or symptoms related to the low activity of EPO or EPO receptors.

Description

technical field [0001] The present invention relates to an erythropoietin mimetic peptide, a preparation method thereof, a pharmaceutical composition containing them and their use in treating diseases characterized by lack of erythropoietin or red blood cell deficiency or defect. Background technique [0002] Erythropoietin (EPO) is a hematopoietic growth factor (HGF) and a glycoprotein necessary for red blood cell production. Containing 165 amino acids, the molecular weight is about 30.4kD, 40% of the molecular weight is the result of glycosylation modification, and the glycosylation sites are asparagine side chain amino N-glycosylation at positions 24, 38, and 83 and 126 Serine side chain hydroxyl O-glycosylation. In humans, EPO is mainly produced in the kidney and liver of the fetus, and is synthesized and released by the peritubular capillary endothelial cells of the renal tubules. As a cytokine, EPO plays a role in promoting red blood cell production in bone marrow he...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/00C07K1/06C07K1/04A61K38/16A61P7/06
CPCA61K38/1816A61P7/06C07K14/505
Inventor 刘克良梁远军常少华许笑宇宫泽辉颜玲娣董华进贾启燕孟庆斌郄建坤
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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