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Selenium peptide and preparation method and application thereof

An enzyme-responsive, selenium amino acid technology, applied in the field of selenopeptides and its preparation, can solve the problems of low release efficiency, difficult penetration, and poor enrichment efficiency, and achieve the effects of reducing toxic and side effects, reducing drug levels, and good therapeutic effects

Active Publication Date: 2021-03-12
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the complex physiological barriers in the human body affect the therapeutic effect of nanomedicine, such as rapid clearance of nanomedicine in blood, poor enrichment efficiency in tumor part, difficulty in penetration in tumor tissue and drug release efficiency in tumor cells Low, these factors hinder the further clinical development of conventional nanomedicine
[0004] At present, nano-drugs targeting tumors generally have the problems of fast metabolism, poor enrichment efficiency, difficulty in penetration and low release efficiency.

Method used

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  • Selenium peptide and preparation method and application thereof
  • Selenium peptide and preparation method and application thereof
  • Selenium peptide and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] This example provides a Boc group protected C 12 Fatty chain-L selenocysteine ​​Boc-L-Sec (C 12 h 25 )-OH, the Boc-L-Sec(C 12 h 25 )-OH preparation method comprises the following steps:

[0118] Take 0.64g of selenium powder and 0.60g of sodium borohydride in a 100mL round bottom flask, add 2mL of water, the selenium powder and sodium borohydride react violently to generate disodium diselenide. The round bottom flask was sealed with a rubber stopper and placed in an oil bath at 50°C with stirring. After 20 min, 0.95 mL of 1-bromododecane was mixed with 10 mL of tetrahydrofuran, injected into the reaction flask through a syringe, and the reaction flask was kept in an oil bath at 50° C. for 12 h. The reaction flask was cooled in an ice-water bath, and 2 mL of an aqueous solution containing 0.3 g of sodium borohydride was added into the round-bottomed flask with a syringe, and stirred at room temperature for 30 min.

[0119] Dissolve 2.74g of N-tert-butoxycarbonyl-O-...

Embodiment 2

[0132] The present embodiment provides a kind of selenopeptide (C 12 -selenopeptide), the structural formula of the selenopeptide is: [L-Sec(C 12 h 25 )-OH]-K[L-Sec(C 12 h 25 )-OH]-GPLGVRGRGD, the selenopeptide is synthesized by polypeptide solid-phase synthesis, specifically comprising the following steps:

[0133] Weigh 300 mg of Rink amide AM resin (amino acid loading rate 0.35 mmol / g) into a 10 mL peptide synthesis tube, add 8 mL of anhydrous DMF to it, place on a shaker overnight to fully swell the resin, and remove DMF with a suction filter pump .

[0134] Add 8 mL of Fmoc deprotecting agent (that is, a mixed solution of DMF and piperidine with a volume ratio of 4:1) to the peptide synthesis tube, react for 10 minutes to remove Fmoc from the amino acid on the resin, and wash alternately with dichloromethane and DMF for 3 Second-rate.

[0135] Take a small amount of resin in a 1mL plastic centrifuge tube, add ninhydrin test solution (that is, a mixture obtained by d...

Embodiment 3

[0142] The present embodiment detects the C prepared by Example 2 12 - the MMP-2 enzyme response ability of the selenopeptide, the specific steps are as follows:

[0143] Combine MMP-2 enzyme with C 12 - The selenopeptides are mixed in PBS buffer solution with a pH of 7.4, and the concentrations of the two after mixing are 50 μg / mL and 120 μmol / L, respectively. The two were reacted at 37°C for 2h. The solution after the reaction is detected by HPLC, wherein, different peak times in the HPLC spectrum correspond to different substances, and the peak area corresponds to the content of the substance. The results are as follows figure 2 shown.

[0144] It can be seen from the figure that after 2 hours of mixed reaction with MMP-2 enzyme, 80% of C 12 - The selenopeptide is cut by MMP-2 enzyme, and a new peak appears at the same time, which proves that a new substance is generated. The new substance was confirmed by MALDI-TOF-MS as [L-Sec(C 12 h 25 )-OH]-K[L-Sec(C 12 h 25 )...

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Abstract

The invention provides a selenium peptide as well as a preparation method and application thereof. The selenium peptide comprises an oxidation response unit, an enzyme response breaking unit and a tumor targeting unit which are sequentially connected from an N end to a C end; wherein the oxidation response unit comprises oxidation response selenium amino acid, and the oxidation response selenium amino acid is aliphatic chain-L-selenocysteine. The invention also provides a self-assembled selenium peptide nano-drug. The self-assembled selenium peptide nano-drug comprises the selenium peptide andan anti-tumor drug. The oxidation response selenium amino acid has the capacity of sensitively responding to an oxidation environment, the selenium peptide has a tumor targeting function, and the particle size is reduced through enzyme response breakage, so that the permeability is improved, and the capacity of accelerating drug release in tumor cells is improved; the self-assembled selenium peptide nano-drug composed of the selenium peptide and an anti-tumor drug has an excellent tumor treatment effect, and is low in toxic and side effects and wide in application prospect.

Description

technical field [0001] The invention belongs to the field of biotechnology and pharmaceutical technology, and in particular relates to a selenopeptide and its preparation method and application. Background technique [0002] Cancer is a disease that seriously endangers people's life and health. Affected by the living environment and unhealthy lifestyle, the incidence and death of cancer have been increasing in recent years. How to effectively treat cancer has always been a major scientific problem for human beings, and it is also one of the focuses of modern medical research. [0003] Chemotherapy plays an important role in cancer treatment. As a systemic treatment, chemotherapy can kill tumor cells in the body to the greatest extent and inhibit tumor recurrence and metastasis. Traditional small-molecule anti-cancer agents such as platinum drugs, paclitaxel and doxorubicin have caused great damage to normal tissues and organs of patients while killing tumor cells. In recen...

Claims

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Application Information

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IPC IPC(8): A61K47/42A61K47/62A61K47/69A61K31/704A61P35/00C07K7/02C07K1/04C07K1/06C07K1/10
CPCA61K47/42A61K47/62A61K47/6929A61K31/704A61P35/00C07K7/02
Inventor 王浩易宇魏子钰
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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