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Extremely acidic pH fluorescent probe, and preparation method and application thereof

A fluorescent probe, acid technology, applied in the field of fluorescent probes, to achieve the effects of reducing interference, great practical value, and simple synthesis steps

Inactive Publication Date: 2014-09-03
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many pH fluorescent probes currently reported focus on the detection of intracellular neutrality, that is, the pH value of the cell fluid and the pH value of acidic organelles such as lysosomes and endosomes; needles are rarely reported

Method used

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  • Extremely acidic pH fluorescent probe, and preparation method and application thereof
  • Extremely acidic pH fluorescent probe, and preparation method and application thereof
  • Extremely acidic pH fluorescent probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of an extremely acidic pH fluorescent probe based on benzindole:

[0025]

[0026] (1) Under the protection of inert gas, mix 0.283g (1.35mmol) 1,1,2-trimethyl-1H-benzo[e]indole with 0.454g (1.48mmol) 3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-propenal Dissolve in 6 mL of DMF, add 0.378 g (6.75 mmol) of KOH solid, stir at room temperature, and react overnight.

[0027] (2) KOH solid was removed by filtration, H2O (6 mL) was added to the reaction solution, and the mixed solution was mixed with CH 2 Cl 2 Extraction (10ml x 3). The combined organic phases were washed with anhydrous Na 2 SO 4 After drying, the crude product was obtained by distillation under reduced pressure.

[0028] (3) The crude product was separated on a silica gel column with dichloromethane as the eluent to obtain an orange-yellow solid. 1 H NMR (300MHz, DMSO-d 6 ), δ: 1.556(s, 6H), 1.648-1.671(d, 6H), 5.009-5.055(m, 1H), 6.607-6.658(m, 2H), 7.037-7.085(m, 1H), 7.178-7.258...

Embodiment 2

[0030] The probe concentration in Example 1 was maintained at 5 μmol / L, the pH was adjusted with 1 mol / L HCl in the ethanol / water (volume ratio of 2:1) system, and its absorption spectrum was recorded ( figure 1 ). With the decrease of pH value, the absorption peak at the short wavelength of 426 nm gradually decreased, the absorption peak at the long wavelength of 546 nm was significantly enhanced, and there was an isoabsorption point at 450 nm. The color of the solution also changed from bright yellow to red ( figure 2 ).

Embodiment 3

[0032] The probe concentration in Example 1 was kept at 5 μmol / L, the pH value was adjusted with 1 mol / L HCl in the ethanol / water (volume ratio of 2:1) system, and the fluorescence emission spectrum was recorded with 426 nm as the excitation wavelength ( image 3 ). The fluorescence peak at 571 nm gradually weakened with the decrease of pH value. Fluorescence intensity at 571 nm was plotted against pH and fitted with sigmoidal ( Figure 4 ), the pKa value of the probe in Example 1 was obtained as 2.89.

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Abstract

The invention discloses an extremely acidic pH fluorescent probe, and a preparation method and application thereof. The pH fluorescent probe is constructed by using butadiene bridged indole or derivatives thereof and 3-[3-(4-fluorophenyl)-1-alkyl-1H-indole on the basis of intramolecular charge transfer effect. The preparation method comprises the following steps: in an inert gas protective atmosphere, dissolving 2,3,3-trimethylindole or 1,1,2-trimethyl-1H-benzo[e]indole and 3-[3-(4-fluorophenyl)-1-alkyl-1H-indolyl-2-yl]-acraldehyde in N,N-dimethylformamide, adding KOH solid, stirring at room temperature, standing over night, concentrating under reduced pressure to obtain a crude product, and separating through a silica gel column to obtain the pure product. The probe has the advantages of lower pKa value, higher sensitivity for H<+>, favorable selectivity and large Stocks displacement. The probe has obvious color variation before and after combination with H<+>, and thus, can be conveniently identified by naked eyes. The probe can penetrate the cytomembrane, and is suitable for intracellular pH value detection and cell imaging.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to an extremely acidic pH fluorescent probe, a preparation method thereof, and the application of the probe in cell imaging. Background technique [0002] pH value not only has a significant impact on the physicochemical properties of substances and their reaction performance, but also many important physiological processes of cells and organelles are closely related to pH value. Excessive acidity and alkalinity can lead to heart, lung disease or neurological disease, and even life-threatening in severe cases. Under normal physiological conditions, H in the cytosol + Its concentration is about 40nmol / L (pH=7.40), and its variation range is generally 0.1-0.2 pH units. There is also a pH range in the cell that is acidic. For example, the pH range of lysosomes is 4.5-5.5, and the pH range of endosomes is 5.4-6.2, which are called acidic organelles. Extremely acidic environments (pH<4) are l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/60G01N21/64
Inventor 牛卫芬樊丽武庭瑄钞建宾双少敏董川
Owner SHANXI UNIV
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