A trinuclear copper alkynyl complex with amino acid recognition function and its preparation method

A technology for amino acids and complexes, applied in the field of amino acid recognition, can solve the problems of rare studies on complexes containing carbonyl groups in ligands, cumbersome pretreatment steps, etc.

Active Publication Date: 2022-04-12
HUIZHOU LEADAO ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above methods generally require the cooperation of large-scale instruments, and the pretreatment steps are cumbersome. The present invention proposes a novel and practical method for detecting cysteine ​​and homocysteine
[0005] Copper(I)alkynyl complexes have attracted a lot of attention worldwide due to their catalytic properties, rich structural diversity and photophysical properties. At present, for the study of trinuclear copper alkynyl complexes, the ligands containing carbonyl Studies on complexes of

Method used

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  • A trinuclear copper alkynyl complex with amino acid recognition function and its preparation method
  • A trinuclear copper alkynyl complex with amino acid recognition function and its preparation method
  • A trinuclear copper alkynyl complex with amino acid recognition function and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] [Cu(CH 3 EN) 4 ](BF 4 )Synthesis:

[0049] 30.3 mmol Cu 2 O was dissolved in 40 mL of acetonitrile, to which 10 mL of HBF was slowly added dropwise 4 to red Cu 2 O completely disappeared, continued adding acetonitrile until the precipitation disappeared, suction filtration to remove unreacted solids, the solvent was removed under reduced pressure, and ether was added to obtain a white solid.

[0050] [Cu 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 Synthesis:

[0051] 8 mmol [Cu(CH 3 EN) 4 ](BF 4 ), 8 mmol of bis(diphenylphosphine)methane, and 40 mL of acetonitrile were added to the flask, and the reaction was carried out under nitrogen protection for 24 hours. Part of the solvent was removed, and ether was added as a white solid (yield 81%).

[0052] [Cu 3 (μ-dppm) 3 (μ 3 -η 1 -C≡CC 6 H 4 -C(O)H-4) 2 ](BF 4 )Synthesis:

[0053] To 0.12 mmol [Cu 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 , 0.15mmol of 4-trimethylsilylethynylbenzaldehyde was added with 0.24mmol...

Embodiment 2

[0057] [Cu(CH 3 EN) 4 ](BF 4 )Synthesis:

[0058] 30.3 mmol Cu 2 O was dissolved in 40 mL of acetonitrile, to which 10 mL of HBF was slowly added dropwise 4 to red Cu 2 O completely disappeared, continued adding acetonitrile until the precipitation disappeared, suction filtration to remove unreacted solids, the solvent was removed under reduced pressure, and ether was added to obtain a white solid.

[0059] [Cu 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 Synthesis:

[0060] 8 mmol [Cu(CH 3 EN) 4 ](BF 4 ), 8 mmol of bis(diphenylphosphine)methane, and 40 mL of acetonitrile were added to the flask, and the reaction was carried out under nitrogen protection for 24 hours. Part of the solvent was removed, and ether was added as a white solid (yield 81%).

[0061] [Cu 3 (μ-dppm) 3 (μ 3 -η 1 -C≡CC 6 H 4 -C(O)H-4) 2 ](BF 4 )Synthesis:

[0062] To 0.12 mmol [Cu 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 , 0.15mmol of 4-trimethylsilylethynylbenzaldehyde was added with 0.24mmol...

Embodiment 3

[0066] UV-Vis absorption spectroscopy titration detection:

[0067] Take the [Cu] prepared in Example 1 3 (μ-dppm) 3 (μ 3 -η 1 -C≡CC 6 H 4 -C(O)H-4) 2 ](BF 4 ) 10μmol / L, and add cysteine, carry out UV-Vis absorption spectrum titration, the results are as follows Figure 4 As shown, it can be concluded that the binding constant of the trinuclear copper alkynyl complex prepared in Example 1 to cysteine ​​is IgK=4.41±0.05.

[0068] Take the [Cu] prepared in Example 1 3 (μ-dppm) 3 (μ 3 -η 1 -C≡CC 6 H 4 -C(O)H-4) 2 ](BF 4 ) 10μmol / L, and added homocysteine, and titrated by UV-Vis absorption spectrum. The results are as follows Figure 5 As shown, it can be concluded that the binding constant of the trinuclear copper alkynyl complex prepared in Example 1 and homocysteine ​​is lgK=4.84±0.11.

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Abstract

The invention provides a trinuclear copper alkynyl complex with amino acid recognition function and a preparation method thereof. The present invention has synthesized trinuclear copper alkynyl complex [Cu 3 (µ‑dppm) 3 (μ 3 ‑η 1 ‑C≡CC 6 h 4 -C(O)H-4) 2 ] BF 4 , the complex has a triplet excited state of charge transfer from the alkyne ligand to the trinuclear copper, enabling specific recognition of cysteine ​​and homocysteine ​​by fluorescence spectroscopy.

Description

technical field [0001] The invention belongs to the technical field of amino acid identification, and particularly relates to a preparation method and application of a trinuclear copper alkynyl complex. Background technique [0002] Cysteine ​​(Cys) and homocysteine ​​(also known as homocysteine, Homocystine, Hcy) are two important amino acids in human metabolism, of which homocysteine ​​is a cysteine ​​metabolic process. the intermediate product. [0003] Concerns about the association of homocysteine ​​with human disease began in the 1970s, and patients with homocysteineuria, as well as small animals that received daily subcutaneous injections of a certain amount of homocysteine, were prone to atherosclerosis Case. In recent years, biomedical research and statistical research have found that homocysteine ​​is related to various diseases. Studies in the 1990s showed that the increase of homocysteine ​​in human blood is an independent factor of cardiovascular disease. It ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08G01N21/31G01N21/33
CPCC07F1/08G01N21/31G01N21/33
Inventor 奚亚男胡淑锦
Owner HUIZHOU LEADAO ELECTRONICS MATERIAL
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