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Polypeptide derivative copper complex, preparation method and application thereof, and anti-cancer drug

A technology of copper complexes and peptide derivatives, applied in the field of biomedicine, can solve the problems of large side effects, drug resistance of tumor cells, etc., and achieve the effects of increasing cell entry, good anti-tumor activity, and low toxicity in vivo

Active Publication Date: 2021-07-13
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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  • Polypeptide derivative copper complex, preparation method and application thereof, and anti-cancer drug
  • Polypeptide derivative copper complex, preparation method and application thereof, and anti-cancer drug
  • Polypeptide derivative copper complex, preparation method and application thereof, and anti-cancer 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) decanoic 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 ...

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 into a stirrer, 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, and success...

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, a preparation method and application thereof and an anti-cancer drug, and belongs to the technical field of biological medicine. The polypeptide derivative copper complex provided by the invention comprises (S)-2-decanoyl amino-3-(1-naphthyl) propionyl-leucyl-valine and CuCl2 (copper chloride). According to the invention, the (S)-2-decanamido-3-(1-naphthyl) propionyl-leucyl-valine is complexed with CuCl2, and the obtained complex can serve as a chelating agent, interacts with endogenous copper and is chelated with the endogenous copper, so that the availability of the complex in tumor growth and angiogenesis is reduced; the polypeptide derivative copper complex provided by the invention can inhibit tumor specific protease and enable the tumor specific protease to be apoptotic, so that good anti-tumor activity is realized; meanwhile, the polypeptide derivative copper complex provided by the invention has the advantages of low in-vivo toxicity and low cost, and can be used as a cheap and safe substitute of 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 Applications(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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