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Glutathione fluorescence probe as well as preparation method and application thereof

A fluorescent probe, glutathione technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of time-consuming and cumbersome process of invertase preparation, and achieve easy large-scale production and detection sensitivity. High, selective and specific effects

Inactive Publication Date: 2014-12-03
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the sensitivity of the enzyme conversion method is high, the process is cumbersome, especially the preparation of the conversion enzyme is very time-consuming
[0007] The fluorescent probe method has high sensitivity, fast response, and simple process. However, due to the similarity in structure of glutathione (GSH), cysteine ​​(Cys), and homocysteine ​​(Hcy), the detection methods currently developed Fluorescent probes for GSH have the same or similar effects on Cys and Hcy

Method used

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  • Glutathione fluorescence probe as well as preparation method and application thereof
  • Glutathione fluorescence probe as well as preparation method and application thereof
  • Glutathione fluorescence probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of Glutathione Fluorescent Probe

[0033] Dissolve 1.861g of 2,4-dinitrofluorobenzene, 1.994g of fluorescein and 2.764g of potassium carbonate in 20mL of anhydrous DMF; under nitrogen protection, react at 75°C for 2 hours; after the reaction, add 20mL of distilled water to wash , filtered, and the obtained solid was dried in a vacuum oven to obtain a crude product; using dichloromethane as an eluent, the crude product was purified on a silica gel column to obtain 2,4-dinitrophenyl fluorescein ether as a yellow solid 1.214g, which is the pure glutathione fluorescent probe ( 1 H-NMR chart and high-resolution mass spectrogram see figure 1 , figure 2 ). The measured molecular weight of the obtained pure fluorescent probe is 664.

[0034] Present embodiment process route:

[0035]

Embodiment 2

[0036] Example 2 The spectral properties of the prepared glutathione fluorescent probe reacting with various amino acids

[0037] Weigh 6.6 mg of the glutathione fluorescent probe prepared in Example 1, and prepare a 10 mL acetonitrile solution with a concentration of 1 mM as the mother solution.

[0038] Fluorescence spectrum test: Add 15 μL of the above mother solution and 1.5 mM cetyltrimethylamine bromide to a certain amount of 20 mM ethanol-PBS buffer solution (3:7v / v, pH7.4), and then add various amino acids: Glutathione, cysteine, homocysteine, glycine, phenylalanine, methionine, glutamic acid, glutamine, lysine, arginine, histidine, alanine One of acid, serine and tyrosine, so that the final concentration of amino acid is 50 μM, and the final concentration of fluorescent probe is 5 μM. After reacting at room temperature for 30 minutes, the fluorescence emission spectrum was measured at the excitation light wavelength of 485nm. The slit width for excitation and emissi...

Embodiment 3

[0043] Example 3 Spectral Properties of Glutathione Fluorescent Probe and Glutathione Reaction Product

[0044] Add 3 μL of the mother solution in Example 2 and 1.5mM CTAB to a certain amount of 20mM ethanol-PBS buffer solution (3:7v / v, pH7.4), and then add different equivalents of glutathione solution to make the fluorescent probe The final concentration of needles was 1 μM, and the final concentrations of glutathione were 0 μM, 1 μM, 2 μM, 3 μM, 4 μM, 5 μM, 6 μM, 7 μM, 8 μM, 9 μM, and 10 μM, respectively. After reacting at room temperature for 30 minutes, measure its fluorescence emission spectrum. The fluorescence emission spectrum is excited at 485nm; the slit width of excitation and emission is 3nm. The resulting fluorescence increment graph is shown in Figure 5 ; Make a working curve with the fluorescence intensity data at 520nm, the results are shown in Image 6 .

[0045] The experimental results show that the fluorescence intensity after the reaction increases with...

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Abstract

The invention relates to a glutathione fluorescence probe as well as a preparation method and an application thereof. A probe structure is shown in a formula (I). The preparation method comprises the following steps of: dissolving 2,4-dinitrofluorobenzene, fluorescein and potassium carbonate into anhydrous dimethyl formamide (DMF); after reaction, preparing the glutathione fluorescence probe; the application of the glutathione fluorescence probe refers to detection on contents of glutathione having non-diagnostic property. According to the glutathione fluorescence probe as well as the preparation method and the application of the glutathione fluorescence probe, the fluorescence reaction only on the fluorescence probe and glutathione is carried out while the fluorescence reaction on the fluorescence probe and other amino acids is avoided, so that the glutathione fluorescence probe has high selectivity and specificity; the preparation process of the probe is easy and feasible, and the probe is easy for scale production.

Description

technical field [0001] The invention relates to a glutathione fluorescent probe, a preparation method and application thereof. Background technique [0002] Thiols play an important role in the antioxidant system of cells and are important components of many proteins and small molecules in living organisms. Small molecule thiols mainly include glutathione (GSH), cysteine ​​(Cys), and homocysteine ​​(Hcy). A large number of physiological phenomena in organisms are considered to depend on the reactions involved in these thiol-containing thiols, such as redox reactions, methyl transfer reactions, and sulfur metabolism reactions in organisms. The concentration of thiols contained in living organisms is considered to be related to many diseases. Deficiency of thiols in the organism can lead to many health problems such as growth retardation, hair loss, lethargy, liver damage, weight loss, and some skin disorders. Glutathione is the most abundant small molecule thiol (1-10mM) i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10G01N21/64C09K11/06
Inventor 陈小强王莉王芳马洋郁文翔
Owner NANJING TECH UNIV
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