Method for synthetizing fullerene bis-addition polypeptide by combining liquid phase and solid phase

A double addition, fullerene technology, applied in the field of medicine, can solve the problems of unreported anti-tumor activity research, complex compound structure, etc., to achieve good anti-cancer activity, good free radical scavenging, and improved solubility.

Inactive Publication Date: 2015-04-01
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many reports on the photodynamics of fullerenes, but the synthesized compounds have complex structures, and there are few further systematic studies in biology. For the research on the photosensitivity and other anti-tumor activities of the nanoparticles of fullerene derivatives It has not been reported

Method used

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  • Method for synthetizing fullerene bis-addition polypeptide by combining liquid phase and solid phase
  • Method for synthetizing fullerene bis-addition polypeptide by combining liquid phase and solid phase
  • Method for synthetizing fullerene bis-addition polypeptide by combining liquid phase and solid phase

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Experimental program
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Effect test

Embodiment 1

[0031] The synthetic route of the fullerene double addition RGD peptide of this embodiment is:

[0032]

[0033] Among them, 1 is N-substituted fullerene double-added pyrrolidine, 2 is fullerene double-added aspartic acid (including Fmoc and OtBu), 3 is fullerene double-added aspartic acid (containing Fmoc), 4 is fullerene double addition RGD peptide.

[0034] The preparation method of the fullerene double addition RGD peptide of the present embodiment is as follows:

[0035] (1) Take 0.24 mmol α-amino and β-carboxyl protected Fmoc-Asp-OtBu, dissolve 0.24 mmol HOBT in 4 mL DCM, add DMF drop by drop until the solution is clear, then add 0.24 mmol DCC and mix well, then protect the ice bath from light with nitrogen React for 30 minutes, filter out the white DCU, then add 0.012 mmol fullerene double-addition pyrrolidine and 3 mg DMAP, protect under nitrogen and avoid light, react for 72 hours, spin evaporate, and separate and purify by silica gel column chromatography, the el...

Embodiment 2

[0041] The preparation method of the fullerene double addition TISWPPR peptide of the present embodiment is as follows:

[0042] (1) Take 0.24mmol α-amino and β-carboxyl protected Fmoc-Glu-OtBu, dissolve 0.24mmol HOBT in 4mL DCM, add DMF drop by drop until the solution is clear, then add 0.24mmol DCC and mix well, then protect the ice bath from light with nitrogen After reacting for 30 minutes, filter off the white DCU, then add 0.024 mmol fullerene double-added pyrrolidine and 3 mg DMAP, protect against light under nitrogen, and react for 48 hours, then rotary evaporate, and separate and purify by silica gel column chromatography, the eluent is toluene / ethyl acetate =3:1, the main product obtained after separation is vacuum-dried to obtain product 2 after rotary evaporation;

[0043] (2) Product 2 was decarboxylated with 90% TFA / DCM, reacted at room temperature for 0.5h, and finally purified by cold ether precipitation to obtain fullerene double-added glutamic acid FBPG (cont...

Embodiment 3

[0046] The preparation method of the fullerene double addition PHLATLF peptide of the present embodiment is as follows:

[0047] (1) Take 0.24 mmol α-amino and β-carboxyl protected Fmoc-Asp-OtBu, dissolve 0.24 mmol HOBT in 4 mL DCM, add DMF drop by drop until the solution is clear, then add 0.24 mmol DCC and mix well, then protect the ice bath from light with nitrogen React for 30 minutes, filter off the white DCU, then add 0.006 mmol fullerene double-added pyrrolidine and 3 mg DMAP, protect against light under nitrogen, and react for 24 hours, then rotary evaporate, and separate and purify by silica gel column chromatography, the eluent is toluene / ethyl acetate =3:1, the main product obtained after separation is vacuum-dried to obtain product 2 after rotary evaporation;

[0048] (2) Product 2 was decarboxylated with 17% TFA / DCM, reacted at room temperature for 12 hours, and finally purified by cold ether precipitation to obtain fullerene double-added aspartic acid FBPD (inclu...

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Abstract

The invention discloses a method for synthetizing fullerene bis-addition polypeptide by combining a liquid phase and a solid phase. N-substitutive fullerene bis-addition pyrrolidine and Fmoc-Asp-OtBu with protected alfa-amino and beta-carboxyl have a condensation reaction with a liquid-phase synthesis method in the presence of DCC (dicyclohexylcarbodiimide), HOBt (hydroxybenzotriazole ) and DMAP (dimethylaminopyridine); after the reaction, separation and purification are conducted through silica-gel column chromatography, and fullerene bis-addition aspartic acid is obtained after deprotection of a product; an alpha-carboxyl of fullerene bis-addition aspartic acid and activated amino on arginine in Wang resin-polypeptide have a condensation reaction with a solid-phase synthesis method, and fullerene bis-addition polypeptide is obtained after deprotection and decomposition of a product. Fullerene bis-addition polypeptide has good anti-tutor activity and capacity for scavenging free radicals, improves the stability of peptide and water solubility of fullerene, can be used for connecting different polypeptide and obtains different biological activity with changing of functional peptide.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a method for preparing a fullerene double-addition polypeptide synthesized by combining liquid and solid phases. The compound greatly improves the solubility of fullerene in polar solutions and improves the biological availability and its targeting to cells. Background technique [0002] Fullerene C 60 Because of its special physical and chemical properties, it shows unique biological activity, which can be classified into photosensitivity and non-photosensitivity effects. The former is related to the light-induced generation of free radicals such as singlet oxygen in the presence of oxygen by fullerene cages, including light-induced DNA breakage, cell membrane damage, and cytotoxicity. The increasing research data shows that fullerene derivatives have a wide range of application prospects in the field of biomedicine, such as photosensitizers in photodynamic therapy, anti-ag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/11C07K7/06C07K1/16C07K1/06C07K1/04C07K1/02
Inventor 张静张晓磊何婷
Owner ZHENGZHOU UNIV
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