A kind of pH fluorescent probe and its application

A probe and pH value 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: 2017-03-15
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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  • A kind of pH fluorescent probe and its application
  • A kind of pH fluorescent probe and its application
  • A kind of pH fluorescent probe and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A pH fluorescent probe whose chemical name is: 1-methyl-2-(4-hydroxy-3-methoxy)styrylpyridinium iodide, and its chemical structure is as follows:

[0023]

[0024] The synthesis steps of the above compounds are as follows:

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

[0026] Melting point determination: mp: 258-261℃

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

[0028] Hydrogen nuclear magnetic resonance spectroscopy: 1 H NMR(400MH Z , DMSO): δ9.77(s, 1H), δ8.88(d, J=6.4H Z , 1H), δ8.49(d, J=7.6H Z , 1H), δ8.4...

Embodiment 2

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

[0034] The melting point determination, infrared spectroscopy determination, and proton nuclear magnetic resonance spectroscopy determination of the product are the same as those in Example 1.

Embodiment 3

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

[0037] The melting point determination, infrared spectroscopy determination, and proton nuclear magnetic resonance spectroscopy determination of the product are the same as those in Example 1.

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Abstract

The invention discloses a pH fluorescent probe, the chemical name is: iodide 1-methyl-2-(4-hydroxyl-3-methoxy) styrylpyridinium salt, and its synthesis method is as follows: iodide 1 , 2-lutidine salt and vanillin are added to n-butanol solution at a molar ratio of 1:1-1:3, piperazine is added, and reacted for 0.5-1 hour under reflux conditions to obtain 1-methyl iodide 2-(4-hydroxyl-3-methoxyl) styryl pyridinium salt, the mass volume ratio of the vanillin and n-butanol solution is 0.304:20-0.456:25; the vanillin and the piperazine The mass ratio of oxazine is 0.456:0.02-0.316:0.01. The color of the solution of the compound of the present invention changes significantly at different pH values, from green to red, and the pH value of the environment can be qualitatively judged by the color change of the solution, and it is a better visual pH fluorescent probe.

Description

Technical field [0001] The invention belongs to the field of organic small molecule fluorescent probes, and specifically relates 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, and are accompanied by changes in the pH of the cell microenvironment. Human intracellular pH 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. Generally, there are two pH ranges in cells, one is near neutral, such as the pH range in the cell sap is 6.8-7.4; the other is acidic, such as the pH range of the lysosome is 4.5-5.5, and the content The body's pH range of 5.4-6.2 is called acidic organelle. Abnormal pH may cause cardiopulmonary and nervous syste...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D213/30G01N21/64C09K11/06
Inventor丁静葛海燕葛燕青李艳玲
OwnerTAISHAN MEDICAL UNIV