Trinuclear copper alkynyl group complex with amino acid recognition function and preparation method of trinuclear copper alkynyl group complex

An amino acid and complex technology, applied in the field of amino acid recognition, can solve the problems of rare research on ligand carbonyl-containing complexes, cumbersome pretreatment steps, etc., and achieve the effects of safe and reliable reaction process, high yield and simple preparation.

Active Publication Date: 2019-12-20
HUIZHOU LEADAO ELECTRONICS MATERIAL
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  • 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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  • Trinuclear copper alkynyl group complex with amino acid recognition function and preparation method of trinuclear copper alkynyl group complex
  • Trinuclear copper alkynyl group complex with amino acid recognition function and preparation method of trinuclear copper alkynyl group complex
  • Trinuclear copper alkynyl group complex with amino acid recognition function and preparation method of trinuclear copper alkynyl group complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

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

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

[0051] 8mmol[Cu(CH 3 EN) 4 ](BF 4 ), 8mmol of bis(diphenylphosphine)methane, and 40mL of acetonitrile were added to the flask, and reacted for 24 hours under nitrogen protection. 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 0.12mmol[Cu] dissolved in 20mL acetonitrile 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 , 0.15mmol 4-trimethylsilylethynyl benzaldehyde, add 0.24mmol KF·2H dissolved in...

Embodiment 2

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

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

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

[0060] 8mmol[Cu(CH 3 EN) 4 ](BF 4 ), 8mmol of bis(diphenylphosphine)methane, and 40mL of acetonitrile were added to the flask, and reacted for 24 hours under nitrogen protection. 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 0.12mmol[Cu] dissolved in 20mL acetonitrile 2 (dppm) 2 (CH 3 EN) 4 ](BF 4 ) 2 , 0.15mmol 4-trimethylsilylethynyl benzaldehyde, add 0.24mmol KF·2H dissolved in...

Embodiment 3

[0066] UV-Vis absorption spectrometry titration detection:

[0067] [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 ultraviolet-visible absorption spectrum titration, the result is as attached Figure 4 As shown, it can be concluded that the binding constant of the trinuclear copper alkynyl complex prepared in Example 1 and cysteine ​​is lg K=4.41±0.05.

[0068] [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 homocysteine, carry out ultraviolet-visible absorption spectrum titration, the result is as attached 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 lg K=4.84±0.11.

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Abstract

The invention provides a trinuclear copper alkynyl group complex with the amino acid recognition function and a preparation method of the trinuclear copper alkynyl group complex. According to the trinuclear copper alkynyl group complex with the amino acid recognition function and the preparation method of the trinuclear copper alkynyl group complex, a trinuclear copper alkynyl complex [Cu3([mu]-dppm)3([mu]3-[eta]<1>-C===CC6H4-C(O)H-4)2]BF4 is synthesized. The complex has a three-wire excited state of charge transfer from alkynyl ligand to trinuclear copper, and the specific recognition of cysteine and homocysteine can be realized by a fluorescence spectrum.

Description

technical field [0001] The invention belongs to the technical field of amino acid recognition, and in particular 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, among which homocysteine ​​is the process of cysteine ​​metabolism intermediate product. [0003] Attention to the link between homocysteine ​​and human disease began in the 1970s. Patients with homocystinuria, as well as small animals given 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 symptom of cardiovascular disease. Risk factor for a ...

Claims

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Application Information

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Patent Type & Authority Applications(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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