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Novel peptide conjugate of African clawed frog GLP-1 (glucagon like peptide-1), as well as application thereof

A technology of glucagon and Xenopus laevis, applied in the field of novel Xenopus laevis glucagon-like peptide-1 conjugated peptides, can solve the problem of reducing the immunogenicity of heterologous proteins, reducing the in vivo clearance rate, and increasing the protein Drug molecular weight and other issues

Active Publication Date: 2017-02-22
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the methods for prolonging the half-life of polypeptide and protein drugs are mainly based on three principles: 1, increase the molecular weight of protein drugs, reduce the glomerular filtration rate; Slowly release the free protein drug, so that the balance between the bound drug and the free drug moves toward the free drug; 3. Reduce the immunogenicity of the heterologous protein, thereby reducing its clearance rate in the body

Method used

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  • Novel peptide conjugate of African clawed frog GLP-1 (glucagon like peptide-1), as well as application thereof
  • Novel peptide conjugate of African clawed frog GLP-1 (glucagon like peptide-1), as well as application thereof
  • Novel peptide conjugate of African clawed frog GLP-1 (glucagon like peptide-1), as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] His-Gly-Glu-Gly-Thr-Tyr-Thr-Asn-Asp-Val-Cys(S-PEG anolog)-Glu-Tyr-Leu-Glu-Glu-Lys-Ala-Ala-Lys-Glu-Phe- Ile-Glu-Trp-Leu-Ile-Lys-Gly-Lys-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Pro-Ser-NH 2

[0086] (SEQ.ID NO:2) solid-phase synthesis (0.1mmol)

[0087] (1) Swelling of the resin

[0088] Weigh 0.262g of Fmoc-Rink amide-MBHA Resin (substitution amount 0.382mmol / g), swell with 7mL DCM for 2min, remove DCM by suction filtration, then swell with 10mL DCM for 30min, and finally rinse with DCM and DMF 7mL respectively.

[0089] (3) Removal of Fmoc protecting group

[0090] Put the swollen resin into the reactor, add 7mL of 20% piperidine / DMF (V / V) solution, shake back and forth at 180°C for 5min in the reactor, the reaction temperature is 25°C, and filter the solution after the reaction; Then add 7 mL of 20% piperidine / DMF (V / V) solution and shake back and forth at 180°C for 15 min in the reactor at a reaction temperature of 25°C. After the reaction, the solution was filtered off an...

Embodiment 2～10

[0103] According to the method described in Example 1, the Xenopus laevis glucagon-like peptide-1 (GLP-1) analogues of Examples 2-10 were synthesized according to the corresponding sequences, and their molecular weights were confirmed by ESI-MS.

Embodiment 2

[0105] His-Gly-Glu-Gly-Thr-Tyr-Thr-Asn-Asp-Val-Thr-Cys(S-PEG anolog)-Tyr-Leu-Glu-Glu-Lys-Ala-Ala-Lys-Glu-Phe- Ile-Glu-Trp-Leu-Ile-Lys-Gly-Lys-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Pro-Ser-NH 2

[0106] (SEQ. ID NO:3)

[0107] The average theoretical relative molecular mass is 6237.9. ESI-MS m / z:calu[M+5H] 5+ 1248.6, [M+6H] 6+ 1040.6;found[M+5H] 5+ 1248.8, [M+6H] 6+ 1040.7.

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Abstract

The invention relates to a novel peptide conjugate of African clawed frog GLP-1 (glucagon like peptide-1), as well as a synthesis method and application thereof. A spiral promoting sequence is introduced to a terminal C of the African clawed frog GLP-1, and meanwhile, PEG (polyethylene glycol)-based modification is performed to obtain an analogue, with reserved hypoglycemic activity and longer pharmacological action time, of the African clawed frog GLP-1. The analogue of the African clawed frog GLP-1 has the advantages of high synthesis yield and low cost, the half-life of the analogue is remarkably prolonged, and the bioactivity is remarkably improved.

Description

technical field [0001] The invention relates to a novel Xenopus laevis glucagon-like peptide-1 (GLP-1) conjugated peptide and its application. Background technique [0002] Diabetes (Diabetes Mellitus) is a chronic systemic disease related to genetic factors and various environmental factors. It is a metabolic disorder of sugar, fat and protein caused by the absolute or relative deficiency of insulin secretion in the body. It is insulin-dependent diabetes (type 1) and non-insulin-dependent diabetes (type 2), wherein type 2 patients account for more than 80% of diabetes cases. Diabetes is a global high incidence, according to the World Health Organization forecast, by 2025 the world's diabetic patients will reach 300 million. A recent epidemiological survey report in China shows that the prevalence of diabetes in China is as high as 9.7%, which is much higher than the global average prevalence of 6.4%. There are about 150 million people at potential risk of diabetes. Curre...

Claims

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Application Information

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IPC IPC(8): C07K14/605C07K1/16A61K38/26A61K47/60A61P3/10A61P3/04
CPCA61K38/00C07K14/605
Inventor 韩京傅俊杰崔旭周凤费颖颖张莹司鹏斌胡月卫婷
Owner XUZHOU NORMAL UNIVERSITY
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