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A compound for detecting copper ions or preparing drugs for preventing and treating Alzheimer's disease, its preparation method and product

A compound, copper ion technology, applied in the biological field, can solve problems such as complex synthesis steps, achieve the effects of inhibiting crosslinking, reducing neurotoxicity, and mild reaction conditions

Inactive Publication Date: 2019-10-29
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These probes can selectively recognize copper ions, and can be used for the detection of copper ions in vitro and in cells, but their disadvantages are that the synthesis steps are complicated, and the detection limit is mostly micromolar.
At the same time, the current copper ion probes only have the function of recognizing copper ions, and there is no report that can simultaneously remove copper ions and inhibit the cross-linking of β-amyloid (Amyloidβ, Aβ)

Method used

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  • A compound for detecting copper ions or preparing drugs for preventing and treating Alzheimer's disease, its preparation method and product
  • A compound for detecting copper ions or preparing drugs for preventing and treating Alzheimer's disease, its preparation method and product
  • A compound for detecting copper ions or preparing drugs for preventing and treating Alzheimer's disease, its preparation method and product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The synthesis of embodiment 1 L1

[0060] Heat and dissolve 10mM (0.96g) 2-imidazole formaldehyde in 10mL of absolute ethanol, add dropwise 10mL of absolute ethanol dissolved in 5mM (0.54g) of 1,2-phenylenediamine, the color of the solution gradually turns yellow, The addition was completed in half an hour, and the mixed solution (78° C.) was refluxed for 12 hours. After the reaction, a large amount of white precipitate was obtained, which was filtered by suction, and the solid was washed with absolute ethanol and anhydrous ether, and dried in vacuo to obtain a white powdery solid, yield: 62.1%, ES-MS (C 2 h 5 OH):265.1([M+H] + ). After structural identification, the structure of ligand L1 is shown in formula I:

[0061]

Embodiment 2

[0062] The synthesis of embodiment 2 L2

[0063] Heat and dissolve 10mM (0.96g) 4-imidazole formaldehyde in 10mL of absolute ethanol, add dropwise 10mL of absolute ethanol dissolved in 5mM (0.54g) of 1,2-phenylenediamine, the color of the solution gradually turns brown, The addition was completed in half an hour, and the mixed solution (78° C.) was refluxed for 12 hours. After the reaction, a large amount of gray-brown precipitate was obtained, which was filtered by suction, and the solid was washed with absolute ethanol and anhydrous ether, and dried in vacuo to obtain gray-brown microcrystals, yield: 50.2%, ES-MS (C 2 h 5 OH):265.1([M+H] + ). After structural identification, the structure of ligand L2 is shown in formula II:

[0064]

Embodiment 3

[0065] Example 3 L1, L2 colorimetric detection of copper ions

[0066] Ligand solution (10% DMSO, 90% H 2 O), in solution, drop different metal ion M solution (M=Li + 、Na + 、K + , Ca 2+ , Mg 2+ 、Ba 2+ 、Al 3+ 、Cd 2+ 、Co 2+ , Hg 2+ , Fe 2+ 、Ni 2+ , Zn 2+ 、Cu 2+ ,10%DMSO,90%H 2 O), observe the solution color change, such as figure 1 As shown, those whose solution color turns green (L1 turns yellow-green, L2 turns light green) are copper ions, and the concentration of copper ions is about 1 mM.

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Abstract

The invention relates to the technical field of biology, in particular to a compound for detecting copper ions and preparing a drug for preventing and treating Alzheimer disease, a preparation method of the compound and a product. The structural formula of the compound is as shown in a formula I or a formula II (as showed in the description). The product can be prepared from cheap and readily available raw materials through one-step synthesis under mild and simple reaction conditions, the two compounds have high selectivity to copper ions and detection limit up to nanomolar level, and can sensitively detect the change of the intracellular copper ion level; and besides, ligands can chelate copper ions, so as to effectively inhibit copper ion-induced cross-linking of amyloid beta-protein, and significantly reduce neurotoxicity caused by cross-linking of amyloid beta-protein, and therefore, the compounds have an important potential value in the field of research and development of Alzheimer disease drugs.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to a compound used for detecting copper ions or preparing drugs for preventing and treating Alzheimer's disease, a preparation method and a product thereof. Background technique [0002] Copper ion is an essential trace element for advanced organs of the human body, and plays an important role in many important physiological processes such as neurotransmitter synthesis and metabolism, antioxidant defense, cellular respiration, and bone synthesis. Abnormal metabolism of copper ions is closely related to the occurrence of Alzheimer's disease, Parkinson's disease, Wilson's disease, fatty liver, diabetes and other diseases. Such as Alzheimer's disease, the higher concentration of copper ions in the patient's brain is one of the key factors leading to the cross-linking and oxidation of β-amyloid. The research on copper ion detection reagents and chelating agents is of great significance to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64G01N21/78G01N21/64A61P25/28
CPCC07D233/64G01N21/6428G01N21/6486G01N21/78
Inventor 于会娟
Owner GUANGDONG UNIV OF TECH
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