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Copper complexes of amino acids and phenanthroline or phenanthroline derivative and preparation method and application thereof

A technology of o-phenanthroline and copper complexes, which can be used in copper organic compounds, drug combinations, antitumor drugs, etc., can solve the problems of not having too much effect, lack of chemical molecular formula and chemical structure of complexes, etc., and achieve a wide range of applications. , the effect of broad action spectrum and high yield

Active Publication Date: 2016-03-30
CAPITAL NORMAL UNIVERSITY
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AI Technical Summary

Problems solved by technology

But their complexes lack exact chemical formulas and chemical structures
In 2004, Guo Zijian reported the complex [Cu(phen)(L-Thr)(H 2 O)(ClO 4 ) (L-Thr is L-threonine), the results of anti-cancer experiments show that it has an inhibitory rate of more than 90% for HL-60 and gastric cancer SGC-7901, but not much for liver cancer BEL-7402 and lung cancer A-549 effect
Guo Zijian's threonine o-phenanthroline copper complex exhibited an inhibitory rate of more than 90% on HL-60 and gastric cancer SGC-7901, but had little effect on liver cancer BEL-7402 and lung cancer A-549

Method used

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  • Copper complexes of amino acids and phenanthroline or phenanthroline derivative and preparation method and application thereof
  • Copper complexes of amino acids and phenanthroline or phenanthroline derivative and preparation method and application thereof
  • Copper complexes of amino acids and phenanthroline or phenanthroline derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0026] Example 1-1, preparation of complex Z1: Glycine (0.5mmol, 0.038g) and NaOH (0.5mmol, 0.02g) were mixed and dissolved in 30ml of ethanol and water mixed solvent (1:1), then Cu(NO 3 ) 2 ·3H 2 O (0.5mmol, 0.119g), stirred until fully dissolved; then added 1,10-phenanthroline (0.5mmol, 0.100g), stirred for 8 hours. Then filter and put the filtrate into a 20ml small test tube, add diethyl ether to the top of the filtrate (volume ratio 1-3), let it stand, and obtain blue crystals in about 20 days. Elemental analysis (%): calculated value (experimental value): C39.53 (39.60); H4.00 (4.01); N13.18 (13.15). Its infrared spectrum and X-diffraction single crystal structure diagram are shown in the attached Figure 1A , 1B and 1C. Z1 compound molecular formula is: {[Cu II (phen)(Gly)(H 2 O)] NO 3 - 2H 2 O} n , that is, 1 1,10-Phen, 1 glycine, 1 H 2 O coordinates with 1 Cu to form a repeating unit ( Figure 1B ). This repeating unit is bridged by Cu to form a one-dimen...

Embodiment 1-2： experiment 1-1，KOH(0.5mmol)NaOH(0.5mmol)。 Embodiment 1-3

[0028] Example 1-2: The experiment was the same as 1-1, except that KOH (0.5 mmol) replaced NaOH (0.5 mmol). Embodiment 1-3: experiment is the same as 1-1, just Cu(ClO 4 ) 2 ·6H 2 O (0.5mmol) and NaNO 3 (0.5mol) to replace Cu(NO 3 ) 2 ·3H 2 O (0.5 mmol). Embodiment 1-4: experiment is the same as 1-1, just Cu(SO 4 ) 2 ·5H 2 O (0.5mmol) and NaNO 3 (0.5mol) to replace Cu(NO 3 ) 2 3H 2 O (0.5 mmol). Embodiment 1-5: experiment is the same as 1-1, just CuCl 2 2H 2 O (0.5mmol) and NaNO 3 (0.5mol) to replace Cu(NO 3 ) 2 ·3H 2 O (0.5 mmol). Embodiment 1-6: experiment is the same as 1-1, just CuBr 2 (0.5mmol) and NaNO 3 (0.5mol) to replace Cu(NO 3 ) 2 ·3H 2 O (0.5 mmol). Embodiment 1-7: experiment is the same as 1-1, just Cu(CH 3 COOH) 2 ·H 2 O (0.5mmol) and NaNO 3 (0.5mol) to replace Cu(NO 3 ) 2 ·3H 2 O (0.5 mmol).

Embodiment 2-1

[0029] Example 2-1, preparation of complex Z2, L-phenylalanine (0.5mmol, 0.083g) and NaOH (0.5mmol, 0.02g) were mixed and dissolved in 30ml of ethanol and water mixed solvent (1:1) ; Then add CuCl 2 2H 2 O (0.5mmol, 0.0874g), then stirred until fully dissolved; then added 1,10-phenanthroline (0.5mmol, 0.099g), stirred for 12 hours; filtered, put the filtrate into a 20ml small test tube, and added diethyl ether To the top of the filtrate (volume ratio 1-3), let it stand, and obtain blue crystals after about a week. Elemental analysis (%): calculated value (experimental value): C50.71 (50.74); H4.86 (4.77); N8.45 (8.54). Its infrared spectrum and X-diffraction single crystal structure diagram are shown in the attached Figure 2A with 2B . Z2 compound molecular formula is: [Cu II (phen)(L-Phe)(Cl)] 2 ·6H 2 O, that is, 1 1,10-Phen, 1 phenylalanine, and 1 Cl coordinate with 1 Cu to form a cis complex; the other 1,10-Phen, 1 phenylalanine Acid, and 1 Cl coordinates with 1 C...

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Abstract

The present invention provides copper complexes of a series of amino acids and phenanthroline or a phenanthroline derivative and a preparation method and application thereof, and the copper complexes are respectively prepared by bonding the amino acids, the phenanthroline or the phenanthroline derivative, and other small molecule ligand with copper ions. The preparation method of the copper complexes is as follows: the series of amino acids, the phenanthroline or the phenanthroline derivative, a copper salt and the small molecule ligand are stirred in an organic solvent for reaction to obtain the complexes. The synthesis raw materials of the copper complexes are easily-available and low in cost, the products are precipitated in crystalline forms, the purity is high, the yield is high, the copper complexes can be stable in the natural state, and by introduction of the amino acids, the copper complexes have good water-soluble and fat soluble and biological-fusion properties. In addition, the complexes show excellent inhibition effects on a plurality of kinds of cancer cells of lung cancer, gastric cancer, liver cancer, colonic adenocarcinoma, leukemia, cancer and the like, and are broad in spectrum of action and wide in range of application.

Description

technical field [0001] The present invention relates to a series of copper complexes of amino acid and o-phenanthroline or derivatives thereof, a preparation method thereof, and the application of the complexes in the preparation of drugs for preventing and treating cancer and tumor diseases. Background technique [0002] Amino acids are the basic structural units of biological macromolecules such as proteins and enzymes in living organisms. Due to the presence of amino and carboxyl groups, amino acids have chelating and buffering properties, and are both hydrophilic and hydrophobic, making amino acids have some unique properties that other organic compounds do not have. Copper is an indispensable and important trace element for the human body. Studies have shown that copper deficiency increases the incidence of gastric cancer, nasopharyngeal cancer, and liver cancer. In 1912, Germany treated patients with facial cancer with a mixture of copper chloride and lecithin. Resea...

Claims

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Application Information

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IPC IPC(8): C07F1/08A61P35/00A61P35/02
Inventor 鲁晓明张波张伟川程一峰孙小静
Owner CAPITAL NORMAL UNIVERSITY
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