Preparation method and application of GSH (glutathione) water-soluble fluorescent probe based on rhodamine

A fluorescent probe, water-soluble technology, applied in the field of fluorescent probes, to achieve the effect of good water solubility and rapid response

Inactive Publication Date: 2017-02-22
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As far as we know, most rhodamine-based fluorescent probes are used to monitor metal cations (Li, D.; Li, C.Y.; Li, Y.F.;

Method used

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  • Preparation method and application of GSH (glutathione) water-soluble fluorescent probe based on rhodamine
  • Preparation method and application of GSH (glutathione) water-soluble fluorescent probe based on rhodamine
  • Preparation method and application of GSH (glutathione) water-soluble fluorescent probe based on rhodamine

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Experimental program
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Effect test

Embodiment 1

[0029] Synthesis of fluorescent probes

[0030] Synthesis of compound Rh1: 1,2,4-Trimellitic anhydride (1.92 g, 10 mmol) and 3-diethylaminophenol (3.30 g, 20 mmol) were added to a 100 mL round bottom flask containing 50 mL of N,N-dimethylformamide , under the protection of nitrogen, the magnetic stirring was refluxed for 6 hours, and the reaction was stopped; after the reaction mixture was cooled to room temperature, twice distilled water (200mL) was added, and after being fully stirred, it was extracted with dichloromethane (100mL×3), and the organic layers were combined and reduced. The solvent was distilled off under pressure. The crude product was separated by column chromatography with dichloromethane / methanol at 6:1 (volume ratio) to obtain a red solid Rh1 (0.419 g, yield: 8.6%). 1 H NMR (400MHz, CD 3 OD)δ8.19(d,J=8.0Hz,1H),8.08(d,J=8.0Hz,1H),7.80(s,1H),7.28(d,J=8.0Hz,2H),6.98(d ,J=8.0Hz,2H),6.89(s,2H),3.64(d,J=8.0Hz,8H),1.28(s,12H). 13 CNMR (100MHz, CD 3 OD)δ164.9,...

Embodiment 2

[0034] Solution preparation of fluorescent probe interacting with GSH

[0035] A certain amount of fluorescent probe was dissolved in water to obtain a concentration of 1.0×10 -4 mol L -1 Probe stock solution. Dissolve a certain amount of GSH in water, transfer it to a 500mL volumetric flask, add water to the mark, and obtain a concentration of 1.0×10 -2 mol L -1 GSH. will be 1.0×10 -2 mol L -1 The GSH solution was gradually diluted with water to obtain 1.0 x 10 -3 -1.0×10 -8 mol L -1 GSH aqueous solution. Add 1.0mL of the probe stock solution and 1.0mL of GSH aqueous solution into a 10mL volumetric flask, and dilute to the volume with buffer solution to obtain a concentration of 1.0×10 -5 mol L -1 fluorescent probe and 1.0 x 10 -3 -1.0×10 - 8 mol L -1 GSH mixed with the solution to be tested.

Embodiment 3

[0037] Measurement of Fluorescence Spectrum of Interaction of Fluorescent Probe with GSH

[0038] A buffer solution with a pH value of 7.4 was used as a solvent to measure the fluorescence spectrum of the fluorescent probe interacting with GSH, and the results were as follows: figure 1 . The concentration of the fluorescent probe is 10μM, the concentration of GSH is 0, 0.08, 1.0, 2.0, 3.0, 5.0, 7.0, 9.0, 11.0, 13.0, 15.0, 20.0, 23.0, 25.0μM, the excitation wavelength is fixed at 510nm, and the emission wavelength The range is 530-650nm, and the slit width is 5.0nm / 5.0nm. From figure 1 It can be seen that before adding GSH, the fluorescent probe has no fluorescence emission peak at 576 nm. With the addition of GSH, the emission peak at 576nm is greatly enhanced, and with the increase of GSH concentration, the fluorescence intensity of the probe is continuously enhanced. When 25 μM GSH is added, the fluorescence intensity is enhanced to 69 without GSH. times. This is becaus...

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Abstract

The invention discloses a preparation method and an application of GSH (glutathione) water-soluble fluorescent probe based on rhodamine. A structural formula of the fluorescent probe is represented in the specification. The invention provides a water-soluble fluorescent probe for detecting GSH with high selectivity on the basis of rhodamine derivatives. 1,2,4-trimellitic anhydride, 3-diethylaminophenol, hydrazine hydrate and glyoxal are taken as raw materials to synthesize the fluorescent probe. On one hand, the rhodamine structure is modified with carboxyl, and water solubility of the probe can be greatly improved; on the other hand, a hydrolysis-addition reaction is performed between SH of an analyte and aldehyde groups of the probe, and GSH, Cys and Hcy are distinguished. The fluorescent probe is the first one capable of efficiently distinguishing GSH, Cys and Hcy in a 100% aqueous solution on the basis of the rhodamine derivatives. The probe shows quite high sensitivity and good selectivity on GSH, and can be applied to cell imaging and detect intracellular GSH.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to a preparation method and application of rhodamine-based GSH water-soluble fluorescent probes. Background technique [0002] In recent years, fluorescent probes have been used as important analytical tools for biological sample monitoring and in vivo fluorescence imaging due to their advantages of high sensitivity, high resolution, nondestructiveness to the sample to be tested, and in situ, real-time, and rapid detection (Que, E.L.; Domaille, D.W.; Chang, C.J. Chem. Rev. 2008, 108, 1517-1549). Most of the fluorescent probes are designed and used to detect metal cations, and few are used to detect small biological molecules (Chen, X.Q.; Pradhan, T.; Wang, F.; Kim, J.S.; Yoon, J.Y. Chem. Rev., 2012, 112, 1910–1956.). Glutathione (GSH), cysteine ​​(Cys) and homocysteine ​​(Hcy) are collectively referred to as biothiols, and they play an important role in life activities ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029G01N21/6428
Inventor 李春艳欧阳娟李勇飞
Owner XIANGTAN UNIV
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