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Application of tumor cell membrane selectively penetrating peptide

A tumor cell and penetrating peptide technology, applied in the field of penetrating peptides, can solve problems such as inability to distinguish between ordinary cells and tumor cells, enhanced efficacy and toxic side effects of anti-tumor drugs, and patient suffering.

Inactive Publication Date: 2011-09-07
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although ordinary membrane-penetrating peptides have many of the above advantages, when they assist anti-tumor drugs or their anti-tumor drug carriers to enter cells, they cannot distinguish between ordinary cells and tumor cells, and cannot selectively play a role in penetrating membranes. Therefore, the efficacy and side effects of antineoplastic drugs will be strengthened at the same time, which will bring more pain to patients

Method used

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  • Application of tumor cell membrane selectively penetrating peptide
  • Application of tumor cell membrane selectively penetrating peptide
  • Application of tumor cell membrane selectively penetrating peptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] RRRRRHHH(R 5 h 3 , R at the C-terminus and N-terminus) as an example to illustrate the method of using solid-phase synthesis of polypeptides.

[0019] Add 1g of Rinkamide-MBHA resin (0.74mmol / g) into a 50mL round-bottomed flask with a branch pipe on the side and a sand plate filter element in the branch pipe, add 20mL DMF to swell for 10 minutes, and remove the solvent by suction filtration. Then 20 mL of 20% piperidine / DMF solution was added, stirred for 30 minutes, and suction filtered. The resin was washed 6 times with DMF, and the solvent was removed by suction filtration. Add 1.44g (2.22mmol) Fmoc-Arg(Pbf)-OH (Pbf is 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl), 0.46g ( 2.22mmol) dicyclohexylcarbodiimide and 0.30g (2.22mmol) HOBt (1-hydroxybenzotriazole) and 20mL DMF, stirring at room temperature for condensation reaction. After 2 hours of reaction, a small amount of resin was taken for ninhydrin color reaction, and the result showed that the condensation...

Embodiment 2

[0023] RRRRRHHH(R 6 h 3 , R at the C-terminus and N-terminus) as an example to illustrate the method of using solid-phase synthesis of polypeptides.

[0024]Add 1.13g of Rinkamide-MBHA resin (0.74mmol / g) into a 50mL round-bottomed flask with a branch pipe on the side and a sand plate filter element in the branch pipe, add 20mL DMF to swell for 10 minutes, and remove the solvent by suction filtration. Then 20 mL of 20% piperidine / DMF solution was added, stirred for 30 minutes, and suction filtered. The resin was washed 6 times with DMF, and the solvent was removed by suction filtration. Add 1.63g (2.51mmol) Fmoc-Arg(Pbf)-OH (Pbf is 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl), 0.52g ( 2.51mmol) of dicyclohexylcarbodiimide and 0.34g (2.51mmol) of HOBt (1-hydroxybenzotriazole) and 20mL of DMF were stirred at room temperature for condensation reaction. After 2 hours of reaction, a small amount of resin was taken for ninhydrin color reaction, and the result showed that th...

Embodiment 3

[0028] RRRRRRRHHH(R 7 h 3 , R at the C-terminus and N-terminus) as an example to illustrate the method of using solid-phase synthesis of polypeptides.

[0029] Add 1.26g of Rinkamide-MBHA resin (0.74mmol / g) into a 50mL round-bottomed flask with a branch pipe on the side and a sand plate filter element in the branch pipe, add 20mL DMF to swell for 10 minutes, and remove the solvent by suction filtration. Then 20 mL of 20% piperidine / DMF solution was added, stirred for 30 minutes, and suction filtered. The resin was washed 6 times with DMF, and the solvent was removed by suction filtration. Add 1.82g (2.80mmol) Fmoc-Arg(Pbf)-OH (Pbf is 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl), 0.58g ( 2.80mmol) dicyclohexylcarbodiimide and 0.38g (2.80mmol) HOBt (1-hydroxybenzotriazole) and 20mL DMF, stirring at room temperature for condensation reaction. After 2 hours of reaction, a small amount of resin was taken for ninhydrin color reaction, and the result showed that the condens...

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Abstract

The invention belongs to the field of the membrane penetrating peptide and particularly relates to a tumor cell membrane selectively penetrating peptide and application thereof. The sequence of the tumor cell membrane selectively penetrating peptide comprises a basic amino acid cluster which is composed of 5 to 12 consecutive arginine residues. The tumor cell membrane selectively penetrating peptide is characterized in that the C or N end of the basic amino acid cluster is connected with three histidine residues. The tumor cell membrane selectively penetrating peptide has cell membrane penetration capacity, can distinguish tumor cells and normal tissue cells and can efficiently penetrate through the tumor cell membrane without penetrating through the normal tissue cell membrane basically.

Description

Technical field: [0001] The invention belongs to membrane-penetrating peptides, in particular to tumor cell-selective membrane-penetrating peptides and applications thereof. Background technique: [0002] In recent years, some peptides with the ability to penetrate the cell membrane, such as TAT, MPG, PEP-1, penetratin, oligoarginine, etc., have gradually become the focus of research in the field of biomedicine. These positively charged polypeptide sequences can pass through the cell membrane without destroying the structure of the cell membrane. These natural or synthetic peptides are water-soluble, low-lying, and can enter various cells through non-phagocytosis, so they are called cell-permeable peptides (CPP), because penetrating peptides were first discovered in the whole Transmembrane transport of chain proteins, so it is also called protein transduction domain (protein transduction domain, PTD). Although the transmembrane mechanism of penetrating peptides is not full...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K7/08A61K47/42A61P35/00A61K47/18
Inventor 周建平吕慧侠孙博张振海张银龙姜天玥
Owner CHINA PHARM UNIV
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