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Imidazo[1,2-a]pyridine near-infrared ratio type pH fluorescence probe and preparation and application thereof

A fluorescent probe, 2-a technology, applied in the field of fluorescent probes, can solve the problems of limited types of pH fluorescent probes and lack of attention in the research and development of pH fluorescent probes, reducing phototoxicity, enhancing ICT effect, and high background interference. Effect

Active Publication Date: 2019-11-05
SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Imidazo[1,2-a]pyridine near-infrared ratio type pH fluorescence probe and preparation and application thereof
  • Imidazo[1,2-a]pyridine near-infrared ratio type pH fluorescence probe and preparation and application thereof
  • Imidazo[1,2-a]pyridine near-infrared ratio type pH fluorescence probe and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1. Probe 4-((1E,3E)-4-(2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)buta-1,3-diene Preparation of -1-yl)-N,N-dimethylaniline:

[0028]

[0029] (1) Under the protection of an inert gas, 4-dimethylaminocinnamaldehyde (10mmol, 1.75g) and 4-chloroaniline (10mmol, 1.29g) were dissolved in 15mL methanol solution, heated to reflux, and reacted for 4h. 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;

[0030] (2) The crude product (10mmol, 2.84g) 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 resulting solid was dissolved in water and treated with CH 2 Cl 2 Extraction, decompression distillation removes solvent and obtains product crude product;

...

Embodiment 2

[0033] 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 value of the system with 1 mol / L of HCl, and records its ultraviolet 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 isoabsorptive point near 431nm.

Embodiment 3

[0035] with H 2 O / DMSO (V / V=4 / 1) system Dilute the probe prepared in Example 1 to a final concentration of 10 μM, adjust the pH value of the system with 1 mol / L HCl, fix the excitation wavelength at 431 nm, and record its fluorescence ll( figure 2 ). With the decrease of pH value, the fluorescence intensity at 560nm decreased gradually, while a new emission peak appeared at 650nm and was significantly enhanced, and an iso-emission point appeared near 611nm.

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Abstract

The invention discloses an imidazo[1,2-a]pyridine near-infrared ratio type pH fluorescence probe, a preparation method of the probe and application of the probe in measuring the extremely-acid pH change in living cells and escherichia coli. Under inert gas protection, 4-dimethylamino-cinnamaldehyde or a derivative thereof, 4-chloroaniline and sodium bicarbonate are dissolved in methyl alcohol, andafter a heating reflux reaction is conducted, a reaction product and 2-(4-methoxyphenyl)-7-methyl imidazo[1,2-a]pyridine are dissolved in N,N-dimethylformamide; potassium tert-butoxide is taken as analkaline reagent, and a heating reflux reaction is conducted; after concentration, silicagel column separation is conducted. Under the extremely acid condition, a transmitted wave of the probe is longer than 600 nanometers, the transmitted wave is located in a near infrared region, a ratio transmission fluorescence characteristic is presented, and the probe has the advantages of high sensitivityand good selectivity for H+, large Stokes displacement and the like.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to an imidazo[1,2-a]pyridine near-infrared ratiometric pH fluorescent probe and a preparation method and application thereof. 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 analy...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06G01N21/33G01N21/64
CPCC07D471/04C09K11/06C09K2211/1007C09K2211/1044G01N21/33G01N21/6428G01N2021/6417
Inventor 张彤鑫徐迪
Owner SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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