Fluorescent probes for detecting formaldehyde, and preparation and application thereof

A fluorescent probe and formaldehyde technology, applied in the field of environmental analytical chemistry and biological detection, can solve the problems of slow detection response, disturbance of endogenous formaldehyde concentration, poor sensitivity, etc., and achieve fast detection response, good stability, and good sensitivity Effect

Active Publication Date: 2017-05-10
杭州汉晶生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, only a small number of fluorescent probes for formaldehyde detection have been reported, and most of them have the problems of slow detection response and poor sensitivity, and some formaldehyde will be consumed while detecting formaldehyde, thereby disturbing the concentration of endogenous formaldehyde in biological samples

Method used

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  • Fluorescent probes for detecting formaldehyde, and preparation and application thereof
  • Fluorescent probes for detecting formaldehyde, and preparation and application thereof
  • Fluorescent probes for detecting formaldehyde, and preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: Preparation of fluorescent probe molecule I-1

[0027] 7-Diethylaminocoumarin (500 mg) and Lawson's reagent (1.86 g) were refluxed in dry toluene for 6 hours. After the reaction, cool and filter, spin the filtrate to dry the solvent, dissolve it in ethanol, add 80% hydrazine hydrate, and react under reflux for 3 hours. After the reaction was completed, the solvent was spin-dried, water was added, extracted three times with dichloroformaldehyde, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain I-1 (65% yield). LC-MS: m / z 232.3010[M+H] + .

[0028]

Embodiment 2

[0029] Embodiment 2: the preparation of fluorescent probe molecule II-1

[0030] 7-Methoxycoumarin (500 mg) and Lawson's reagent (1.86 g) were refluxed in dry toluene for 6 hours. After the reaction, cool and filter, spin the filtrate to dry the solvent, dissolve it in ethanol, add 80% hydrazine hydrate, and react under reflux for 3 hours. After the reaction was completed, the solvent was spin-dried, water was added, extracted three times with dichloroformaldehyde, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain II-1 (yield 70%). LC-MS: m / z 191.2066[M+H] + .

Embodiment 3

[0031] Embodiment 3: Fluorescence changes before and after the reaction of fluorescent probe molecule I-1 with formaldehyde

[0032] Dissolve the probe molecule in a small amount of DMSO, and add PBS buffer or formaldehyde in PBS solution respectively, so that the final concentration of the probe molecule is 10 μM, and the final concentration of formaldehyde is 500 μM. After reacting for 10 minutes, use a fluorescence spectrometer to excite at 450nm, record the fluorescence intensity of the solution at the maximum emission wavelength (about 500nm), and then confirm that the fluorescence intensity of the probe molecule is enhanced after the reaction with formaldehyde, such as figure 1 shown.

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Abstract

The invention provides a type of fluorescent probes for detecting formaldehyde. The probes have the structures shown as formulas I to IV. Benzene ring correspondingly substituted coumarin is firstly subjected to backflow reaction with Lawson reagents in toluol; an obtained product continuously performs backflow reaction with hydrazine hydrate in ethanol. The fluorescent probes per se provided by the invention do not have fluorescence in the water solution, but can take a specific fast reaction with formaldehyde to produce products with strong fluorescence, so that the specific sensitive detection and quantitative analysis of formaldehyde is realized. The stability is high; the long-time storage use can be realized; the detection signal-to-noise ratio is high; the sensitivity is high; the excellent selectivity is realized; the specific formaldehyde detection in complicated biological samples can be realized; good biomembrane permeability is realized, so that the fluorescent probes can be used for formaldehyde detection in living cells; the detection reaction is fast; the detection result can be given within 1 minutes for formaldehyde in the water solution; during the formaldehyde detection, the formaldehyde concentration in the environment cannot be influenced. The general molecular formulas of the probes provided by the invention are shown as the accompanying drawing.

Description

technical field [0001] The invention belongs to the field of environmental analysis chemistry and biological detection, and relates to a fluorescent probe for detecting formaldehyde, a preparation method thereof and an application in detecting the formaldehyde content in the environment and biological samples. Background technique [0002] Formaldehyde is a colorless gas with a special pungent smell, which is irritating to human eyes and nose. High concentrations of formaldehyde in the environment have toxicity such as sensitization, teratogenicity and carcinogenicity to the human body, so formaldehyde was identified as a class 1 carcinogen in 2006. Therefore, it is an important and practical work to detect the formaldehyde content in the environment, especially in furniture, newly decorated spaces, new clothing materials, and even food. [0003] The toxic effects of high concentrations of formaldehyde in the environment have been deeply studied at home and abroad. However...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/04C07D491/052C07D493/04G01N21/64
CPCC07D311/04C07D491/052C07D493/04G01N21/643G01N21/6486
Inventor 李新韩益丰梁星光卢应梅韩峰
Owner 杭州汉晶生物科技有限公司
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