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Fluorescent compound with sensing function on arylamine lung cancer marker and preparation and application of fluorescent sensing film prepared from fluorescent compound

A technology of fluorescent compounds and aromatic amines, applied in steroids, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of sensitivity and selectivity that are difficult to meet the actual detection

Active Publication Date: 2016-11-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the detection of aromatic amines has attracted more and more attention, the sensitivity and selectivity of the currently reported sensing systems are difficult to meet the needs of actual detection.

Method used

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  • Fluorescent compound with sensing function on arylamine lung cancer marker and preparation and application of fluorescent sensing film prepared from fluorescent compound
  • Fluorescent compound with sensing function on arylamine lung cancer marker and preparation and application of fluorescent sensing film prepared from fluorescent compound
  • Fluorescent compound with sensing function on arylamine lung cancer marker and preparation and application of fluorescent sensing film prepared from fluorescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A method for preparing a fluorescent compound having a sensing function for arylamine lung cancer markers, comprising the following steps:

[0063] 1) Under argon protection, add 1g of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride to 20mL of propionic acid, stir thoroughly at room temperature for 30 minutes, then quickly add 1.2 mL of compound R was heated up to 140°C and refluxed for 10 hours. After cooling to room temperature, the reaction solution was poured into water, and after suction filtration, the filter cake was washed three times with secondary water, and the obtained solid was fully dried with ethyl acetate:petroleum ether=20:1 as the eluent for column chromatography. The prepared red solid is compound 1.

[0064] Among them, the molar ratio of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride, compound R and propionic acid is 1:4:146;

[0065] R is And n=2.

[0066] 2) Under argon protection, add 0.16g of compound 1 and 0.14g of 4-ami...

Embodiment 2

[0074] A method for preparing a fluorescent compound having a sensing function for arylamine lung cancer markers, comprising the following steps:

[0075] 1) Under argon protection, add 1g of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride to 20mL of propionic acid, stir thoroughly at room temperature for 30 minutes, then quickly add 1.25 mL of compound R was heated up to 140°C and refluxed for 10 hours. After cooling to room temperature, the reaction solution was poured into water, and after suction filtration, the filter cake was washed three times with secondary water, and the obtained solid was fully dried with ethyl acetate:petroleum ether=20:1 as the eluent for column chromatography. The prepared red solid is compound 1.

[0076] Among them, the ratio of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride, compound R, and propionic acid is 1:4.2:146.

[0077] R is And n=2.

[0078] 2) Under argon protection, add 0.16g of compound 1 and 0.15g of 4-amino...

Embodiment 3

[0085] A method for preparing a fluorescent compound having a sensing function for arylamine lung cancer markers, comprising the following steps:

[0086] 1) Under argon protection, add 1g of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride to 20mL of propionic acid, stir thoroughly at room temperature for 30 minutes, then quickly add 1mL of The compound R was heated up to 140°C and refluxed for 10 hours. After cooling to room temperature, the reaction solution was poured into water, and after suction filtration, the filter cake was washed three times with secondary water, and the obtained solid was fully dried with ethyl acetate:petroleum ether=20:1 as the eluent for column chromatography. The prepared red solid is compound 1.

[0087] Among them, the ratio of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride, compound 1, and propionic acid is 1:3.3:146.

[0088] Among them, R is And n=2.

[0089] 2) Under argon protection, add 0.16g of compound 1 and 0.16...

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Abstract

The invention discloses a fluorescent compound with a sensing function on an arylamine lung cancer marker and preparation and application of a fluorescent sensing film prepared from the fluorescent compound, and belongs to the technical field of fluorescent compound preparation. The fluorescent compound contains a cholesterol segment and a perylene unit, the cholesterol segment has the advantages of having a rigid framework, multiple chiral centers, a high van der Waals interaction and the like, perylene has the high fluorescent quantum yield, the good photochemical stability and the high pi-pi accumulation effect, and through the construction units, the prepared fluorescent compound simultaneously has a supermolecular property and an extremely rich assembling behavior. The prepared sensing film is controllable in microtopography, good in photochemical stability, high in sensitivity and capable of being recycled and has important significance on early diagnosis of lung cancer patients.

Description

technical field [0001] The invention belongs to the technical field of preparation of fluorescent compounds and the preparation of sensing thin films, and specifically relates to the preparation and application of fluorescent compounds capable of sensing aromatic amine lung cancer markers such as aniline and o-toluidine, and fluorescent sensing thin films. Background technique [0002] Lung cancer is a common cancer with a high mortality rate. Studies have found that its early diagnosis is extremely critical for the treatment of lung cancer. However, the existing technology is not enough, and its early diagnosis can only rely on regular health checks. In the study, it was found that the breath of lung cancer patients, including early-stage patients, often contains higher levels of aromatic amine gases such as aniline and o-toluidine than healthy people. These two types of aromatic amine gases are also recognized markers of lung cancer. In addition, aromatic amine organic am...

Claims

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Application Information

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IPC IPC(8): C07J43/00C09K11/06G01N21/64
CPCY02P20/582C07J43/003C09K11/06C09K2211/1011C09K2211/1029G01N21/643
Inventor 房喻尚丛娣王刚彭浩南贺美霞常兴茂范佳云刘凯强
Owner SHAANXI NORMAL UNIV
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