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PH fluorescent probe and application of same

A probe and synthesis method technology, applied in the field of pH fluorescent probes, can solve the problems of small Stokes displacement and excitation light interference, and achieve the effects of reducing interference, high sensitivity and simple operation.

Inactive Publication Date: 2015-12-09
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Stokes shift of many pH fluorescent probes reported so far is relatively small, and they are easily interfered by excitation light during imaging.

Method used

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  • PH fluorescent probe and application of same
  • PH fluorescent probe and application of same
  • PH fluorescent probe and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A pH fluorescent probe, its chemical name is: iodide 1-methyl-2-(4-hydroxyl-3-methoxy) styryl pyridinium salt, its chemical structural formula is as follows:

[0023]

[0024] The synthetic steps of above-mentioned compound are as follows:

[0025] Weigh 0.235g (1.0mmol) 1,2-lutidine iodide and 0.316g vanillin in a 50ml round bottom flask, add 20ml n-butanol, add 0.01g piperazine, heat the mixed solution to reflux, and react 45min. After the reaction was detected by TLC, it was cooled to room temperature, and a large amount of solids were precipitated. After suction filtration under reduced pressure, n-butanol was recrystallized to obtain 0.215 g of yellow solids, with a yield of 58.3%.

[0026] Melting point determination: mp: 258-261°C

[0027] Infrared spectrometry: TR (KBr, cm -1 )3439, 3103, 1634, 1618, 1594, 1566, 1522, 1247, 1128

[0028] H NMR spectrum determination: 1 HNMR (400MH Z , DMSO): δ9.77 (s, 1H), δ8.88 (d, J=6.4H Z , 1H), δ8.49 (d, J=7.6H Z ...

Embodiment 2

[0033] Weigh 0.235g of 1,2-lutidine iodide and 0.304g of vanillin into a 50ml round bottom flask, add 20ml of n-butanol, add 0.01g of piperazine, heat the mixed solution to reflux, and react for 30min. After the reaction was detected by TLC, it was cooled to room temperature, a large amount of solids were precipitated, filtered under reduced pressure, and n-butanol was recrystallized to obtain 0.214 g of a yellow solid. Yield 58.0%.

[0034] The melting point determination of product, infrared spectrum determination, proton nuclear magnetic resonance spectrum determination are all with embodiment 1.

Embodiment 3

[0036] Weigh 0.235g of 1,2-lutidine iodide and 0.456g of vanillin into a 50ml round bottom flask, add 25ml of n-butanol, add 0.02g of piperazine, heat the mixed solution to reflux, and react for 60min. After the reaction was detected by TLC, it was cooled to room temperature, and a large amount of solids were precipitated, filtered under reduced pressure, and n-butanol was recrystallized to obtain 0.215 g of a yellow solid. Yield 58.3%.

[0037] The melting point determination of product, infrared spectrum determination, proton nuclear magnetic resonance spectrum determination are all with embodiment 1.

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Abstract

The invention discloses a pH fluorescent probe chemically named iodized-1-methyl-2-(4-hydroxy-3-methoxy)styryl pyridinium salt. A synthetic method includes the following steps: adding iodized-1,2-dimethyl pyridinium salt and vanillic aldehyde into a n-butyl alcohol solution according to the molar ratio of 1:1-1:3, adding piperazine and performing a reaction under reflux for 0.5-1 h to obtain the iodized-1-methyl-2-(4-hydroxy-3-methoxy)styryl pyridinium salt, wherein the mass volume ratio of the vanillic aldehyde to the n-butyl alcohol solution is 0.304:20-0.456:25; and the mass ratio of the vanillic aldehyde to the piperazine is 0.456:0.02-0.316:0.01. The compound is very obvious in solution color change under different pH values, wherein the color is converted into red from green, so that the pH value of environment can be determined according to the color change of the solution. The compound is an excellent visual pH fluorescent probe.

Description

technical field [0001] The invention belongs to the field of small organic molecule fluorescent probes, in particular to a pH fluorescent probe and its application. Background technique [0002] pH is a measure of the acidity and alkalinity of a solution. Many cell biochemical processes, such as cell growth, involve the protonation and deprotonation of biomolecules, accompanied by changes in the pH of the cellular microenvironment. The pH value in human cells is closely related to many important physiological processes of cells, enzymes and tissues, such as cell proliferation and apoptosis, drug resistance, ion transport, endocytosis and muscle contraction. Usually there are two pH ranges in cells, one is near neutral, such as the pH range of 6.8-7.4 in the cell fluid; the other is acidic, such as the pH range of lysosomes is 4.5-5.5, the connotation The body has a pH range of 5.4-6.2 called acidic organelles. Abnormal pH can lead to cardiopulmonary and nervous system dise...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/30G01N21/64
Inventor 丁静葛海燕葛燕青李艳玲
Owner TAISHAN MEDICAL UNIV
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