Preparation method and application of near infrared GSH (glutathione) fluorescent probe

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve the problems of limited application and achieve rapid response

Inactive Publication Date: 2016-08-31
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few rhodamine-based probes have been reported for the detection of glutathione.
In addition, the absorption and emission of rhodamine-based fluorescent probes are only in the visible region (500–600 nm), which limits their application in bioimaging

Method used

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  • Preparation method and application of near infrared GSH (glutathione) fluorescent probe
  • Preparation method and application of near infrared GSH (glutathione) fluorescent probe
  • Preparation method and application of near infrared GSH (glutathione) fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of fluorescent probes

[0033] Synthesis of Compound 1: Cyclohexanone (6.4mmol, 0.66mL) was added dropwise to concentrated sulfuric acid (7.0mL) cooled to 0°C, followed by the addition of 2-((4-diethylamino)-2-hydroxybenzene Formyl)benzoic acid (3.2mmol, 1.003g), magnetically stirred and refluxed for 1.5 hours, and the reaction was stopped; after the reaction mixture was cooled to room temperature, the reaction mixture was poured into a beaker containing 50g of ice water under stirring, and then 0.7mL of 70% perchloric acid immediately produced a large amount of red precipitate. After suction filtration and drying, a red solid compound 1 was obtained, which was directly used in the next reaction without further purification. 1 H NMR (400MHz, CDCl 3 )δ8.30(d, J=8.0Hz, 1H), 7.78(t, J=7.2Hz 1H), 7.69(t, J=7.6Hz 1H), 7.22(d, J=7.5Hz, 1H), 7.06 -7.13(q,2H),6.89(s,1H),3.61-3.66(q,4H),3.07-3.18(m,2H),2.29-2.31(m,2H),1.99(s,2H),1.79 (s,2H),1.34(t,J=6.6Hz,6H).MS(TO...

Embodiment 2

[0038] Solution preparation of fluorescent probe interacting with GSH

[0039] A certain amount of fluorescent probe was dissolved in H 2 In the mixed solution of O / EtOH (9:1, v / v), the concentration obtained is 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 -1GSH 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

[0041] Measurement of Fluorescence Spectrum of Interaction of Fluorescent Probe with GSH

[0042] 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 10 μM, the concentration of GSH is 0, 0.5, 2.0, 4.0, 6.0, 8.0, 10.0, 12.0, 14.0, 16.0, 18.0, 20.0, 22.0, 25.0 μM, the excitation wavelength is fixed at 690 nm, and the emission wavelength The range is 720-800nm, 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 750 nm. With the addition of GSH, the emission peak at 750nm is greatly enhanced, and with the increase of GSH concentration, the fluorescence intensity of the probe is continuously enhanced. When 20 μM GSH is added, the fluorescence intensity is enhanced to 64 times. This is because the ald...

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Abstract

The invention discloses a preparation method and application of a near infrared GSH (glutathione) fluorescent probe. The structural formula of the fluorescent probe is shown as the accompanying drawing. On one hand, the Rhodamine wavelength is increased by 1,3,3-Trimethyl-2-(formylmethylene)indoline, so that the wavelength is prolonged to be 750nm; on the other hand, SH of an analyte and an aldehyde group of the probe take an addition-hydrolysis reaction for realizing GSH, Cys (cysteine) and Hcy(homocysteine) distinguishing. The near infrared GSH fluorescent probe is the first near infrared fluorescent probe which is based on rhodamine derivatives and can efficiently distinguish the GSH, the Cys and the Hcy; the probe shows high sensitivity on the GSH. When the pH value is 6.0 to 8.0, the determination on the GSH by the fluorescent probe is not influenced; the fluorescent probe and the GSH response is fast; the probe cannot be interfered by other biological mercaptan (Cys and Hcy) and other 19 kinds of amino acids; good selectivity is shown. More importantly, the near infrared GSH fluorescent probe can be applied to optical imaging and detection of GSH in cells and tissues.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a preparation method and application of a near-infrared GSH fluorescent probe. Background technique [0002] Glutathione (GSH), cysteine ​​(Cys) and homocysteine ​​(Hcy) are collectively referred to as biothiols, which play an important role in many physiological and pathological processes (Document 1: Shang, L.; Qin, C.J.; Wang, T.; Wang, M.; Wang, L.X.; Dong, S.J.J. Phys. Chem. C. 2007, 111, 13414-13417.). In cells, GSH is the most abundant of the three at 1.0-15 mM (Document 2: Hassan, S.S.M.; Rechnitz, G.A. Anal. Chem. 1982, 54, 1972-1976.). Studies have shown that abnormal levels of glutathione are related to many diseases, including cancer, liver damage, AIDS, Alzheimer's disease, and aging caused by diseases (document 3: Estrela, J.M.; Ortega, A.; Obrador, E. Crit. Rev. Clin. Lab. Sci. 2006, 43, 143-181. Literature 4: Herzenberg, L.A.; De Rosa, S.C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6486
Inventor 李春艳谢俊英李勇飞
Owner XIANGTAN UNIV
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