Novel chitosan derivative simulating the structure of cell-penetrating peptide

A kind of technology of chitosan derivative and penetrating peptide, applied in the field of biomedicine

Inactive Publication Date: 2010-06-30
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, chitosan derivatives that have a membrane-penetrating peptide structure and can carry or promote physiologically active substances to penetrate cells, mucous membranes, digestive tracts, skin, blood-brain barriers and other physiological barriers of various organisms have basically not been reported yet.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of chitosan modified by arginine and phenylalanine (N-arginine-N-phenylalanine chitosan)

[0026] Dissolve chitosan (Mw20000) (2g) in (150ml) 2% acetic acid solution, stir until completely dissolved, about 24h, add a certain amount of arginine (0.98g) protected by BOC anhydride, BOC anhydride protected Phenylalanine (1.25g), NHS (1.35g) and EDC (5.58g), stirred for 48h, added 2ml of trifluoroacetic acid, stirred at room temperature for 24h, dialyzed with dialysis bag (MWCO 3500), freeze-dried, after drying, 2.2 g of a water-soluble light yellow powder was obtained.

[0027] FTIR: 1615.97 (arginine guanidine group), 1526.23, 1563.58 (amide bond formed by arginine and phenylalanine), 3086.12, 1532.31, 701.59 (phenyl ring of phenylalanine).

[0028] The degree of substitution of arginine and the degree of substitution of phenylalanine are 17% as measured by elemental analysis combined with nuclear magnetic resonance.

Embodiment 2

[0030] Membrane Penetrating Ability Experiment of N-Arginine-N-Phenylalanine Chitosan

[0031] Compared with chitosan (Mw20000), it shows the membrane-penetrating ability of N-arginine-N-phenylalanine chitosan; N-arginine-N-phenylalanine chitosan is based on the Prepared in Example 1, both chitosan and N-arginine-N-phenylalanine chitosan were labeled with FITC fluorescein.

[0032] ECV-304 was cultured in RPMI 1640 medium containing 10% calf serum, 100 mg / L each of ampicillin and streptomycin. at 37°C, 5% CO 2 , cultured normally under fully saturated humidity, and subcultured once every 3 days.

[0033] Take a ninety-six-well plate, add coverslips, and inoculate ECV-304 cells at a density of 2×10 5cells / well, cultivated overnight, after the cells adhered to the wall, replace the fresh culture medium, remove the culture medium after 30min, and replace with chitosan or N-arginine-N-phenylalanine chitosan containing the same concentration 1mL of 1640 medium (no serum, no dou...

Embodiment 3

[0036] N-Arginine-N-Phenylalanine Chitosan Promotes Gastrointestinal Absorption of Insulin

[0037] Preparation of insulin-N-arginine-N-phenylalanine solution: 10 mg of insulin (potency 29.5 IU / mg, the same below) was dissolved with a small amount of dilute hydrochloric acid, and 10 mg of N-arginine prepared according to Example 1 was added Acid-N-phenylalanine, adjust the pH to 7.4 with 0.1 mol / L NaOH, and dilute to 50 mL with PBS buffer at pH 7.4.

[0038] Preparation of insulin solution for intragastric administration: Dissolve 10 mg of insulin with a small amount of dilute hydrochloric acid, adjust the pH to 7.4 with 0.1 mol / L NaOH, and dilute to 50 mL with PBS buffer with pH 7.4.

[0039] Preparation of insulin solution for subcutaneous injection: Dissolve 10 mg of insulin with a small amount of dilute hydrochloric acid, adjust the pH to 7.4 with 0.1 mol / L NaOH, and adjust the volume to 250 mL with PBS buffer with pH 7.4.

[0040] The SD diabetic rats were randomly divid...

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Abstract

The invention belongs to the field of biomedicine, particularly to a novel chitosan derivative simulating the structure of cell-penetrating peptide and preparation method and application thereof. The invention has the beneficial effects that the invention provides a chitosan derivative which simulates the structure of cell-penetrating peptide, is relatively simple in structure and easy to synthesize and is provided with or promotes physiological active substances to penetrate the cells, the mucosa, the digestive tract, the skin, the hemato encephalic barrier and other physiological barriers of various organisms.

Description

technical field [0001] The invention belongs to the field of biomedicine, specifically, it is a novel chitosan derivative imitating a penetrating peptide structure, a preparation method and application thereof. Background technique [0002] In recent years, some peptides with cell membrane penetration ability, such as TAT ​​peptide, MPG, PEP-1, penetratin, octaarginine, etc., have gradually become the focus of attention. They can efficiently pass through the cell membrane without the cell membrane being damaged. These natural or synthetic peptides can carry various molecules or nano-carriers into various cell membranes, and are called membrane-penetrating peptides. Studies have found that although the structures of various penetrating peptides are quite different, and different types of penetrating peptides do not have a common amino acid sequence, comprehensive analysis shows that they all have the following two common characteristics: (1) Positive charge. CPPs are general...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/36A61K45/00A61K31/675A61K38/28
Inventor 吕慧侠张振海潘睿睿周建平陈箐清
Owner CHINA PHARM UNIV
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