Novel coumarin two-photon sulfydrylamino acid fluorescent probe

A technology of thiol amino acid and two-photon fluorescence, applied in the field of fluorescent probes, can solve the problems of expensive instruments, complicated operation steps, long response time, etc., and achieve high selectivity

Inactive Publication Date: 2020-03-13
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have disadvantages such as complex operation steps, expensive instruments, long response time, and short excitation wavelength.

Method used

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  • Novel coumarin two-photon sulfydrylamino acid fluorescent probe
  • Novel coumarin two-photon sulfydrylamino acid fluorescent probe
  • Novel coumarin two-photon sulfydrylamino acid fluorescent probe

Examples

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Effect test

Embodiment 1

[0023] The synthesis of embodiment 1 compound I

[0024] Under nitrogen atmosphere and ice bath, 2,4-dinitrobenzenesulfonyl chloride and compound II were added to 20 mL of dry dichloromethane, and triethylamine was added dropwise. After stirring at room temperature overnight, the reaction was completed and concentrated in vacuo, and separated by column chromatography to obtain compound I as a dark red solid. figure 1 is the NMR image of the probe.

Embodiment 2

[0025] The selectivity analysis of embodiment 2 compound I

[0026] Add the DMSO solution containing thiol amino acid to the 10 μM compound I DMSO and PBS buffer mixture (volume ratio: 2:98, 1 mM CTAB), so that the final concentration of thiol amino acid is 50 μM, mix After homogenization, the fluorescence intensity change of the solution was detected, and the results were as follows: figure 2 . When the excitation light wavelength is 480nm, the probe compound I has a strong orange fluorescence at 617nm for glutathione, cysteine, and homocysteine, and the probe compound I has no important response to other non-sulfhydryl amino acids . It shows that the probe compound I has excellent selectivity to glutathione, cysteine ​​and homocysteine.

Embodiment 3

[0027] Example 3 Analysis of the response of probe compound I to changes in the concentration of thiol amino acids

[0028] Add solutions containing different concentrations of glutathione, cysteine, and homocysteine ​​to 10 μM probe compound I in DMSO and PBS buffer mixture (volume ratio 2:98, 1mM CTAB) , the fluorescence intensity at 617nm changes regularly with the increase of glutathione, cysteine ​​and homocysteine, such as image 3 The results shown. The fluorescence intensity was plotted against the concentration, showing a linear relationship, indicating that the probe compound I detects the concentration of various thiol amino acids.

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Abstract

The invention discloses a two-photon fluorescent probe for detecting sulfydrylamino acid, and belongs to the technical field of analytical chemistry. The probe is prepared from a prepared novel coumarin dye and 2,4-dinitrobenzenesulfonyl chloride in dichloromethane at room temperature. The fluorescent probe has the advantages of easily available preparation raw materials, simple synthesis method,and high selectivity, high sensitivity and low detection limit to the sulfydrylamino acid, and can be applied to detection of sulfydrylamino acid in the environment or cells.

Description

technical field [0001] The invention provides a two-photon fluorescent probe for detecting thiol amino acids, belonging to the technical field of fluorescent probes. [0002] technical background [0003] Cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) are three very important sulfhydryl amino acids in cells, also known as biothiols. They not only participate in the oxidation-reduction reaction process in organisms to protect cells from oxidative stress damage, but also regulate cell homeostasis and cell metabolism in organisms. First, in the process of biological growth and development, the lack of cysteine ​​(Cys) can lead to growth retardation, hair loss of pigment, and liver damage. Secondly, the increase of homocysteine ​​(Hcy) content in human plasma is closely related to diseases such as Alzheimer's disease, cardiovascular disease and osteoporosis. Glutathione (GSH) plays an important role in maintaining a reducing environment in cells, including keeping...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
CPCC07D417/04C09K11/06G01N21/6428C09K2211/1007C09K2211/1037C09K2211/1088
Inventor 吕正亮孙鑫范春华
Owner UNIV OF JINAN
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