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Long-acting Exendin-4 analogue and application thereof

An analogue, exenatide technology, applied in the field of long-acting exenatide analogues, can solve the problems of prolonging the half-life of GLP-1, and achieve the effects of prolonging the biological half-life, improving efficiency, and avoiding local itching

Inactive Publication Date: 2016-09-14
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the peptide is also rapidly filtered and eliminated in the kidney, the degradation by anti-DPP-IV enzymes can only prolong the half-life of GLP-1 to a certain extent

Method used

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  • Long-acting Exendin-4 analogue and application thereof
  • Long-acting Exendin-4 analogue and application thereof
  • Long-acting Exendin-4 analogue and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063]

[0064] microwave-facilitated solid-phase synthesis

[0065] (1) Cysteine ​​synthesis with side chain modification

[0066] Weigh 0.21g of Fmoc-Cys-OH, dissolve in DCM, add 0.12g N-n-octylmaleimide, 3ul DIEA as a catalyst, stir and react at room temperature for 4 hours, after the completion of the TLC monitoring reaction, the reaction The solution was concentrated under reduced pressure and separated by column chromatography to obtain 0.27 g of the product with a yield of 79%.

[0067] MS (70eV) m / z: 575.6 ([M+Na] + ).

[0068] (2) Swelling of the resin

[0069] Weigh 50 mg of Fmoc-Rink amide-MBHA Resin (substitution amount 0.4 mmol / g), swell with 7 mL of DCM for 30 min, remove DCM by suction filtration, then swell with 10 mL of NMP for 30 min, and finally rinse with NMP, DCM, and 7 mL of NMP respectively.

[0070] (3) Microwave promotes removal of Fmoc protecting group

[0071] Put the swollen resin into the reactor, add 7mL of 25% piperidine / NMP (V / V) solutio...

Embodiment 2～9

[0085] According to the method described in Example 1, the Exendin-4 analogues of Examples 2-9 were synthesized according to the corresponding sequences, and their respective molecular weights were confirmed by electrospray mass spectrometry (ESI-MS).

Embodiment 2

[0087]

[0088] The theoretical relative molecular mass is 4426.8. ESI-MS m / z: found[M+3H] 3+ 1476.6, [M+4H] 4+ 1107.7;calu[M+3H] 3+ 1476.8, [M+4H] 4+ 1107.9.

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Abstract

The invention relates to a long-acting Exendin-4 analogue and a synthesis method thereof. Exendin-4 is transformed to obtain the Exendin-4 analogue having longer pharmacological action time, synthesis of a target polypeptide is rapidly achieved by a microwave-promoted solid phase synthesis method, and a crude product is purified and freeze-dried to obtain the Exendin-4 analogue.

Description

technical field [0001] The invention relates to long-acting exenatide (Exendin-4) analogs in the field of diabetes treatment and applications thereof. Background technique [0002] Diabetes is the third chronic non-communicable disease that seriously threatens human health after tumors and cardiovascular diseases. Currently, there are about 300 million diabetics in the world, which is expected to increase to 500 million by 2025. Clinically, intensive insulin therapy is used to delay the progression of diabetes. Insulin therapy can reverse the damage of pancreatic β-cell function to a certain extent while lowering blood sugar. However, there is a risk of hypoglycemia with insulin. Affected by factors such as dose size, injection site, injection route, individual differences or not eating after injection, if insulin is used carelessly, severe hypoglycemia side effects will occur. [0003] Glucagon-like peptide-1 (GLP-1) is a glucose-dependent incretin hormone. GLP-1 stimula...

Claims

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Application Information

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IPC IPC(8): C07K14/575A61K38/22A61P3/10
CPCC07K14/57563A61K38/00
Inventor 黄文龙钱海孙李丹蔡星光韩京褚莹莹周洁
Owner CHINA PHARM UNIV
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