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Preparation method of active peptide with snake venom source

A peptide compound, N-terminal technology, applied in the field of anti-tumor, biomedicine, to achieve the effect of high purity, low cost, and simple and easy preparation method

Inactive Publication Date: 2015-03-25
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pyroglutamic acid is formed by cyclization of glutamic acid. This step is catalyzed by pyroglutamate enzyme in the venom gland of snake venom. However, no pyroglutamate enzyme or pyroglutamate enzyme has been extracted from snake venom gland so far. A report on the cyclization of N-terminal glutamic acid of polypeptide by other means
Since the existing solid-phase synthesis technology can usually only provide polypeptides with glutamic acid at the N-terminal, it is necessary to cyclize the glutamic acid at the N-terminal to achieve the desired activity

Method used

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  • Preparation method of active peptide with snake venom source
  • Preparation method of active peptide with snake venom source
  • Preparation method of active peptide with snake venom source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 : Peptide samples with N-terminal glutamic acid Synthesis

[0030] Weigh 0.6779g (0.59mmol / g) of Fmoc-Trp-Wang Resin and place it in the reactor of the peptide synthesizer, add 10ml of DMF and mix for 1 hour to fully swell the resin. Add 10ml of 25% PIP (DMF) solution, mix for 30 minutes, and wash with DMF. After washing, the coupling reaction can be carried out. Add 0.7591g Fmoc-Lys(Trt)-OH, 2.5 ml of 0.64mol / L HOBT (DMF) solution, 3 ml of 0.53mol / L DIC (DMF) solution and 3ml of DMF into the mixing reactor for reaction, the reaction temperature is room temperature, The end point of the reaction was determined by ninhydrin reaction to obtain Fmoc-Lys(Trt)-Trp-Wang Resin.

[0031] After the coupling reaction is finished, wash with 10ml DMF, add 10ml of DMF solution of 25% PIP, carry out deprotection for 30min, wash with DMF after the reaction is finished, add 0.6831g Fmoc-Glu(OtBU)-OH to the reactor, and 0.64mol / L HOBT (DMF) solution 2.5 ml, 0.53mol / L DI...

Embodiment 2

[0036] Dissolve the Glu-Lys-Trp tripeptide obtained in Example 1 in a sodium phosphate buffer solution with a pH of 2, control the sample concentration to 1 mg / ml, add 0.1 mol / l CuCl 2 Three drops. Heated in a water bath at 60°C for 4 hours, and freeze-dried the solution to obtain pyroGlu-Lys-Trp. The product was analyzed by mass spectrometry using a Q-Tof mirco (Waters company) mass spectrometer, see attached figure 1 .

Embodiment 3

[0038] The Glu-Gln-Trp obtained in Example 1 was dissolved in a sodium phosphate buffer solution with a pH of 6, the sample concentration was controlled to be 3 mg / ml, and 0.1 mol / l of CuCl was added 2 Three drops. Heated in a water bath at 85°C for 2 hours, and freeze-dried the solution to obtain pyroGlu-Gln-Trp. The product was analyzed by mass spectrometry using a Q-Tof mirco (Waters company) mass spectrometer, see attached image 3 .

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Abstract

The invention belongs to the field of biological medicine, and relates to a preparation method of a active peptide with snake venom source and application thereof in the antineoplastic aspect. The invention concretely relates to a chemical method for preparing a peptide compound with pyroglutamic acid as N terminal, and concrete purpose of the peptide compound in the antineoplastic field. The invention also relates to a chemical synthetic method of pyroGlu-Lys-Trp, pyroGlu-Asn-Trp or pyroGlu-Gln-Trp, and application of the tripeptides compound in the antineoplastic field.

Description

[0001] This application is a divisional application of a Chinese invention patent application with an application date of April 29, 2010, an application number of 201010158898.7, and the title of the invention is a preparation method of a group of active peptides derived from snake venom and its application in antitumor. technical field [0002] The invention relates to the field of biomedicine, in particular to a chemical method for preparing a peptide compound whose N-terminal is pyroglutamic acid, and the specific use of this peptide compound in the anti-tumor field. Background technique [0003] Snake venom is a natural mixture secreted by the venomous glands of venomous snakes, including proteins, polypeptides and enzymes. It has biological activities such as anticoagulation, analgesia, promoting nerve growth and inhibiting tumor cell growth. It is one of the important natural compound libraries for research and development of new drugs. The anti-tumor components in snak...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/097A61K38/06A61P35/00
Inventor 吴勇冯军张喜全徐宏江薛春佳马宇旋
Owner SHANGHAI INST OF PHARMA IND CO LTD
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