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A copper complex of polypeptide derivatives, its preparation method and application, and an anticancer drug

A technology of copper complexes and peptide derivatives, applied in the field of biomedicine, can solve problems such as large side effects and drug resistance of tumor cells, and achieve the effects of increasing cellularity, good anti-tumor activity and low cost

Active Publication Date: 2022-05-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, cisplatin has relatively large side effects, such as nausea, vomiting, loss of appetite, diarrhea, etc., and has neurotoxicity and nephrotoxicity; at the same time, long-term application of cisplatin can also make tumor cells develop drug resistance

Method used

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  • A copper complex of polypeptide derivatives, its preparation method and application, and an anticancer drug
  • A copper complex of polypeptide derivatives, its preparation method and application, and an anticancer drug
  • A copper complex of polypeptide derivatives, its preparation method and application, and an anticancer drug

Examples

Experimental program
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Effect test

preparation example Construction

[0041] In the present invention, the preparation method of (S)-2-decanoylamino-3-(1-naphthyl)propionyl-leucyl-valine preferably comprises the following steps:

[0042] (1) L-Val-OBzl and Boc-Leu undergo the first condensation reaction to obtain Boc-Leu-Val-OBzl;

[0043] (2) The Boc-Leu-Val-OBzl reacts with the first deprotecting reagent to obtain HCl Leu-Val-OBzl;

[0044] (3) Boc-3-(1-naphthyl)-L-alanine carries out the second condensation reaction with the HCl Leu-Val-OBzl to obtain Boc-3-(1-naphthyl)-propionyl- Leucyl-valine benzyl ester;

[0045] (4) The Boc-3-(1-naphthyl)-propionyl-leucyl-valine benzyl ester reacts with the second deprotection reagent to obtain HCl NH 2 -3-(1-naphthyl)-propionyl-leucyl-valine benzyl ester;

[0046] (5) Capric acid and the HCl NH 2 -3-(1-naphthyl)-propionyl-leucyl-valine benzyl ester undergoes a third condensation reaction to obtain (S)-2-decanoylamino-3-(1-naphthyl)propionyl- Leucyl-valine benzyl ester;

[0047] (6) In flow H 2 Un...

Embodiment 1

[0094] Example 1 (S)-2-decanoylamino-3-(1-naphthyl) propionyl-leucyl-valine (abbreviated as C 10 Preparation of NalLeuVal)

[0095] (1) Preparation of Boc-Leu-Val-OBzl

[0096] Weigh 1.15g (5mmol) Boc-Leu, 0.96g (5mmol) EDC, 0.68g (5mmol) HOBt, put them into a stirring bar, add 20mL acetonitrile, activate in ice bath for 20min, weigh 1.35g (5.5mmol) HCl H -Val-OBzl was added to the eggplant bottle, and 2 mL of NMM was added to adjust the pH to 9, and the reaction was carried out at room temperature for 12 hours. The reaction was monitored by TLC (ethyl acetate / petroleum ether 1:2, Rf=0.3), and the raw material point disappeared to terminate the reaction. Remove the organic solvent with a rotary evaporator to obtain a yellow viscous sample, add ethyl acetate, and obtain a light yellow suspension by ultrasonication, add distilled water, and the solution is layered. Pour the mixed solution into a separatory funnel, discard the lower liquid, keep the upper ethyl acetate layer, a...

Embodiment 2

[0116] Example 2 Polypeptide Derivative Copper Complex Cu-C 10 Preparation of NalLeuVal

[0117] ①Weigh 3.4mgCuCl 2 2H 2 O, add 1mL of distilled water to dissolve, the solution is clear and light blue.

[0118] ②Weigh 11.6mg of (S)-2-decanoylamino-3-(1-naphthyl)propionyl-leucyl-valine, add CuCl prepared above 2 In the solution, ultrasonic 30min, the solution is milky.

[0119]③ After the above emulsion was freeze-dried at -20°C for 10 hours with a freeze dryer, a yellow-green solid was obtained, which was the polypeptide derivative copper complex Cu-C 10 NalLeuVal, denoted as C10NLVCu.

[0120] The obtained polypeptide derivative copper complex Cu-C 10 The infrared spectrum of NalLeuVal is as follows figure 2 shown.

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Abstract

The invention provides a polypeptide derivative copper complex, its preparation method and application, and an anticancer drug, belonging to the technical field of biomedicine. The polypeptide derivative copper complex provided by the present invention comprises (S)-2-decanoylamino-3-(1-naphthyl) propionyl-leucyl-valine and CuCl 2 . The present invention combines (S)-2-decanoylamino-3-(1-naphthyl) propionyl-leucyl-valine with CuCl 2 Complexation, the resulting complex can act as a chelating agent, interact with endogenous copper and chelate endogenous copper, thereby reducing its availability in tumor growth and angiogenesis; the polypeptide derivative copper complex provided by the invention It can inhibit tumor-specific proteases and make them apoptosis, achieving good anti-tumor activity. At the same time, the polypeptide derivative copper complex provided by the invention has the advantages of low toxicity in vivo and low cost, and can be used as a cheap and safe substitute for platinum drugs.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a polypeptide derivative copper complex, a preparation method and application thereof, and an anticancer drug. Background technique [0002] Cisplatin is a metal platinum complex, which belongs to cell cycle non-specific antineoplastic drugs, can damage DNA, inhibit tumor growth, has broad antibacterial spectrum, and is effective against hypoxic cells, and is widely used in clinical practice. However, cisplatin has serious side effects, such as nausea, vomiting, loss of appetite, diarrhea, etc., and has neurotoxicity and nephrotoxicity; meanwhile, long-term application of cisplatin can also lead to drug resistance of tumor cells. [0003] In recent years, many scholars have devoted themselves to developing new metal complexes with better antitumor activity, fewer side effects, and lower drug resistance to replace cisplatin therapy. Copper is an essential trace element in all...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/087C07K1/107A61K33/34A61K45/06A61K47/64A61P35/00
CPCC07K5/0812A61K33/34A61K47/64A61K45/06A61P35/00
Inventor 王玉记冯琦琦樊宇坤高洁贾翌江阿依江范保瑞
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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