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Angiogenesis inhibiting peptide, hyaluronic acid modified compound thereof and preparation method and application of hyaluronic acid modified compound

A technology of hyaluronate and modifier, applied in the field of biomedicine, can solve the problems of limited application of polypeptide drugs, poor water solubility, poor stability, etc., and achieve the effects of strong activity, increased half-life and high stability

Active Publication Date: 2017-10-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with other peptides such as ES-2, the water solubility of Anti-flt1 peptide is poor, which greatly affects its function
[0004] In summary, most of the existing peptide angiogenesis inhibitors have problems such as short half-life in vivo and poor stability, which limits the application of polypeptide drugs in the preparation of angiogenesis inhibitors

Method used

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  • Angiogenesis inhibiting peptide, hyaluronic acid modified compound thereof and preparation method and application of hyaluronic acid modified compound
  • Angiogenesis inhibiting peptide, hyaluronic acid modified compound thereof and preparation method and application of hyaluronic acid modified compound
  • Angiogenesis inhibiting peptide, hyaluronic acid modified compound thereof and preparation method and application of hyaluronic acid modified compound

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Embodiment 1

[0053] Embodiment 1: Preparation of ES-2-AF peptide

[0054] The molecular weight of the ES-2-AF peptide of the present invention is 2197.5Da. It is synthesized by Fmoc solid phase, purified by high performance liquid phase, and confirmed by means of mass spectrometry and high performance liquid chromatography. The purity can reach more than 95%. .

Embodiment 2

[0055] Example 2: Preparation of ES-2-AF peptide hyaluronic acid modification (HA-ES-2-AF)

[0056] The preparation steps are as follows:

[0057] (1) Wash the Dowex ion exchange resin with water, add excess tetrabutylamine hydroxide TBA-OH (24.5ml), and mix well. Dowex-TBA resin was obtained, and the supernatant was removed by filtration. Sodium hyaluronate NaHA (1 g) was dissolved in water and poured into the prepared Dowex-TBA resin (10 g). After mixing for 3 hours, filter with a 0.45 μm syringe filter to remove Dowex resin to obtain a clear HA-TBA solution, which was lyophilized for 3 days.

[0058] (2) HA-TBA and ES-2-AF peptide prepared in step (1) were dissolved in DMSO respectively. After HA-TBA is fully dissolved, add excess Carter condensing agent BOP to activate HA carboxyl, and mix for 30 minutes. Then the HA-TBA solution, the peptide solution, and an equimolar amount of DIPEA were mixed and dissolved in DMSO. After reacting for 24 hours, an equal volume of 1M ...

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Abstract

The invention discloses an angiogenesis inhibiting peptide, a hyaluronic acid modified compound thereof and a preparation method and application of the hyaluronic acid modified compound. The amino acid sequence of an ES-2-AF peptide is represented by SEQ ID NO.1 in a sequence table; and the hyaluronic acid modified compound of tge ES-2-AF peptide is formed by amino groups of the ES-2-AF peptide and carboxy groups on hyaluronic acid molecules through bonding of amido bonds, and the structural formula is HA-CO-NH-(ES-2-AF)n. Compared with an anti-flt1 peptide and an ES2 peptide, the ES-2-AF peptide has the advantage that the capacity of inhibiting angiogenesis is preserved and even enhanced. Compared with the ES-2-AF peptide, the hyaluronic acid modified compound has the advantages that the antiangiogenic activity and anti-tumor activity of the ES-2-AF peptide are preserved, the properties of antiangiogenesis and the like of macromolecule hyaluronic acid are integrated, and the hyaluronic acid modified compound has the characteristics of relatively high stability, relatively strong hydrophilcity and targeting property and the like, so that the hyaluronic acid modified compound has relatively good use effects and application values.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a preparation method and application of an angiogenesis inhibitory peptide and a hyaluronic acid modified product thereof. Background technique [0002] Endostatin (Endostatin, ES) is a 20KDa polypeptide isolated from hemangioendothelioma, which is identified as the C-terminal part of collagen XVIII. Endostatin can directly target the endothelial cells near the tumor without obvious toxicity to normal cells. It can also inhibit the proliferation and migration of endothelial cells and cause apoptosis. Its anti-angiogenic activity is achieved by regulating the expression of vascular endothelial growth factor VEGF. ES-2 (IVRRADRAAVP) is a short peptide segment in the ES structure that has obvious anti-angiogenesis and anti-tumor activities. It is easier to enter the cell interior, and it is easier to obtain and modify. However, like ES, ES-2 also exists in the body The shortc...

Claims

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Application Information

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IPC IPC(8): A61K38/39A61K38/08A61K47/61A61P35/00A61P19/02A61P9/10A61P3/10A61P27/02
CPCA61K38/08A61K38/39A61K2300/00
Inventor 谭海宁于洋孙凤邢亮杨志芳王振东
Owner SHANDONG UNIV
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