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A kind of indolizine carboxylic acid pH fluorescent probe and its application

A technology of fluorescent probe and pyridine carboxylic acid, which is applied in the fields of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, and can solve the problems of pH fluorescent probe application that has not been reported in the literature and applications in the field of optics.

Inactive Publication Date: 2018-03-27
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Indolizine compounds are restricted by limited synthesis methods, and their applications in the optical field have been rarely reported, and their applications as pH fluorescent probes have not been reported in the literature.

Method used

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  • A kind of indolizine carboxylic acid pH fluorescent probe and its application
  • A kind of indolizine carboxylic acid pH fluorescent probe and its application
  • A kind of indolizine carboxylic acid pH fluorescent probe and its application

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Experimental program
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Effect test

Embodiment 1

[0014] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0015]

[0016] Concrete synthetic steps are as follows:

[0017] Add 2.31g (10.0 mmol) ethyl 2-acetylindolizine-7-carboxylate, 0.80 g (20.0 mmol) sodium hydroxide, and 20 mL 95% ethanol to a 50 mL round-bottomed flask, and reflux at 80 degrees After reacting for 2-5 hours, pour it into 300 mL of water, adjust the pH to 5-6 with concentrated hydrochloric acid, a large amount of solid precipitates, filter with suction, and dry to obtain 1.86 g of a yellow solid product with a yield of 91.6%.

[0018] H NMR spectrum determination: 1 H NMR (400 MHz, DMSO-d 6 ):δ12.96 (s, 1H), 8.31 (m, 2H),8.39 (s, 1H), 7.13 (s, 1H), 7.04(m, 1H),2.51 (s, 3H). 13 C NMR (100 MHz, DMSO-d 6 ): 194.37, 166.79, 131.61, 129.65, 126.48, 124.23, 121.21, 118.98, 111.41, 104.44, 28.09.

[0019] Such as figure 2 , image 3 shown.

Embodiment 2

[0021] Get indolizine carboxylic acid 0.0020g, be dissolved in 10mL dimethyl sulfoxide, obtain probe mother liquor, concentration is 10 -3 M. Take 100 microliters of the probe mother solution and add it to 10mL of dimethyl sulfoxide aqueous solution with different pH (dimethyl sulfoxide: water = 2:8) to measure the change of the fluorescence emission intensity and find that the pH changes from 2.6 to 7.5 In the middle, the fluorescence intensity at 430 nm was significantly enhanced, such as figure 1 shown.

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Abstract

The invention discloses an indolizine carboxylic acid pH fluorescent probe, the probe is 2-acetyl indolizine-7-carboxylic acid, and its chemical structural formula is shown in formula (1). The fluorescent probe of the present invention has unique fluorescence selectivity and higher sensitivity to pH in an aqueous solution of dimethyl sulfoxide. Compared with existing probes, it has a narrow pH corresponding range and is not subject to background interference. It is suitable for It has significant advantages such as pH detection in strongly acidic environments, and has great application prospects.

Description

[0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a novel pH fluorescent probe 2-acetyl indolizine-7-carboxylic acid and its application. Background technique [0002] As an important indicator of cell health, pH plays an important role in cell growth, proliferation, apoptosis, autophagy, ion transport, and other cellular processes. Small changes in it can lead to cellular dysfunction and serious diseases, such as colorectal cancer, breast cancer, cystic fibrosis, neurodegenerative diseases and even Alzheimer's disease. However, the commonly used glass electrode pH measurement method is not suitable for the detection of pH in the field of life. [0003] Fluorescent probes have good selectivity, high sensitivity, simple operation, low cost and real-time monitoring. They have been used as a preferred test tool for the determination of intracellular pH. Although a variety of pH fluorescent probes have been reported, the rese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D471/04G01N21/64
CPCC07D471/04C09K11/06C09K2211/1029G01N21/643
Inventor 葛燕青段桂运曹晓群董建
Owner TAISHAN MEDICAL UNIV
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