Imidazo[1,2-a]pyridine-based ratiometric pH fluorescent probe and its preparation method and application

A fluorescent probe, 2-a technology, applied in the field of fluorescent probes, can solve the problems of limited types of pH fluorescent probes, lack of attention in research and development, etc., to overcome the interference of photobleaching and cell autofluorescence, and to achieve good cell permeability , Good biocompatibility effect

Active Publication Date: 2022-05-10
SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, there is a lack of attention to the development of pH fluorescent probes for extremely acidic (pH<4) environments, resulting in a very limited variety of pH fluorescent probes in this area

Method used

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  • Imidazo[1,2-a]pyridine-based ratiometric pH fluorescent probe and its preparation method and application
  • Imidazo[1,2-a]pyridine-based ratiometric pH fluorescent probe and its preparation method and application
  • Imidazo[1,2-a]pyridine-based ratiometric pH fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Preparation of probe 4-(2-(2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)vinyl)-N,N-dimethylaniline :

[0043]

[0044] (1) Under the protection of an inert gas, N,N-dimethylbenzaldehyde (10mmol, 1.49g), 4-chloroaniline (10mmol, 1.29g), was dissolved in 15mL of anhydrous methanol, heated to reflux, reaction 4 -5h. The reaction solution was cooled to room temperature, poured into a large amount of distilled water, extracted with dichloromethane solvent, and the organic solvent was distilled off under reduced pressure to obtain a crude product;

[0045] Wherein, the volume ratio of dehydrated alcohol and distilled water is 15-20:150-200;

[0046] (2) The crude product (10mmol, 2.58g) obtained in (1), 2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine (10mmol, 2.38g ) and potassium tert-butoxide (25mmol, 2.81g) were dissolved in 20mL DMF, and heated at 90°C for 15h. The reaction solution was cooled to room temperature, poured into a large amount of distilled wate...

Embodiment 2

[0050]

[0051] (1) Under the protection of an inert gas, dissolve N,N-diphenylbenzaldehyde (10mmol, 2.73g), 4-chloroaniline (10mmol, 1.29g) in 15mL methanol solution, heat to reflux, and react 4- 5h. The reaction solution was cooled to room temperature, poured into a large amount of distilled water, extracted with dichloromethane solvent, and the organic solvent was distilled off under reduced pressure to obtain a crude product;

[0052] (2) The crude product (10mmol, 2.58g) obtained in (1), 2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine (10mmol, 3.82g ) and potassium tert-butoxide (25mmol, 2.81g) were dissolved in 20mL DMF, and heated at 90°C for 15h. The solvent was removed under reduced pressure, and the resulting solid was dissolved in water and washed with CH 2 Cl 2 extraction. Remove the solvent to obtain the product crude product;

[0053] (3) (2) product crude product is separated and purified through silica gel column, V 乙酸乙酯 :V 正己烷 =1:1 as the eluent, ...

Embodiment 3

[0055] The probe prepared in Example 1 was prepared as a stock solution with a concentration of 1 mM in DMSO (dimethyl sulfoxide) and stored. H 2 O / DMSO (V / V=4 / 1) system dilutes the probe to a final concentration of 10 μM, adjusts the pH range of the system to 6.5-2.2 with 1mol / L HCl, and records its UV absorption spectrum ( figure 1 ). With the decrease of the pH value, the absorption peak at the short wavelength gradually decreases, and the absorption peak at the long wavelength increases significantly, and there is an isosbestic point near 402nm.

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Abstract

The invention proposes an imidazo[1,2-a]pyridine ratiometric pH fluorescent probe and a preparation method thereof, and the probe is used for the determination of extremely acidic pH changes in living cells and Escherichia coli. The preparation method is as follows: under the protection of an inert gas, N, N-dimethylbenzaldehyde or its derivatives, 4-chloroaniline and sodium bicarbonate are dissolved in methanol, and heated to reflux to obtain a crude product; and 2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine dissolved in N,N-dimethylformamide, with potassium tert-butoxide as alkaline reagent, heating Reflux reaction; separated by silica gel column. The probe exhibits ratiometric emission fluorescence characteristics under extremely acidic conditions, and at the same time has the ability to H + It has the advantages of high sensitivity, good selectivity and large Stokes shift.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to an imidazo[1,2-a]pyridine ratiometric pH fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen ions are one of the important intracellular substances and play an important role in regulating the functions of cells, enzymes and tissues. The pH values ​​within different prokaryotes as well as within different subcellular organelles of eukaryotic cells range from alkaline to strongly acidic. Many diseases are associated with abnormal concentrations of hydrogen ions in cells, leading to diseases such as inflammation, cancer and Alzheimer's disease. Therefore, sensitive and accurate real-time monitoring of intracellular pH can provide important information for studying the physiological and toxicological processes of cells at the molecular level. [0003] Among the many methods for detecting intracellular pH, fluorescence analysis has ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC09K11/06C07D471/04G01N21/6428G01N21/6447C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 张彤鑫徐迪
Owner SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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