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A kind of extremely acidic pH fluorescent probe and its preparation method and application
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A fluorescent probe, acidic technology, applied in the field of fluorescent probes, to achieve the effect of reducing interference, great practical value, and simple synthesis steps
Inactive Publication Date: 2016-03-30
SHANXI UNIV
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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
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Embodiment 1
[0024] Preparation of a benzindole-based extremely acidic pH fluorescent probe:
[0025]
[0026] (1) Under the protection of an 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]-acrolein was dissolved in 6 mL of DMF, 0.378 g (6.75 mmol) of KOH solid was added, stirred at room temperature, and reacted overnight.
[0027] (2) Remove the KOH solid by filtration, add H to the reaction solution 2 O (6mL), mixed solution with CH 2 Cl 2 Extraction (10 mL 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 HNMR (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 (m,2H),7.309-7.364...
Embodiment 2
[0030] The probe concentration in Example 1 was maintained at 5 μmol / L, and the pH value was adjusted with 1mol / L HCl in the ethanol / water (volume ratio of 2:1) system, and its absorption spectrum was recorded ( figure 1 ). As the pH value decreases, the absorption peak at the short wavelength of 426nm gradually decreases, and the absorption peak at the long wavelength of 546nm is significantly enhanced, and there is an isosbestic point at 450nm. 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, and the pH was adjusted with 1 mol / L of HCl in the ethanol / water (volume ratio of 2:1) system, with 426nm as the excitation wavelength, and its fluorescence emission spectrum was recorded ( image 3 ). As the pH value decreased, the fluorescence peak at 571nm gradually weakened. Fluorescence intensity at 571 nm was plotted against pH and fitted using sigmoidal ( Figure 4 ), the pKa value that obtains the probe among the embodiment 1 is 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 an application of the probe in cell imaging. Background technique [0002] The pH value not only has a significant impact on the physical and chemical properties of substances and their reaction performance, but also many important physiological processes of cells and organelles are also closely related to the pH value. Excessive acidity and alkalinity can lead to heart, lung disease or neurological diseases, and even life-threatening in severe cases. Under normal physiological conditions, H in the cytosol + The concentration is about 40nmol / L (pH=7.40), and its fluctuation range is generally 0.1 to 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 envi...
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