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Novel cell membrane specific formaldehyde fluorescent probe as well as preparation method and application thereof

A fluorescent probe and compound technology, applied in the field of fluorescent probes, can solve problems such as long response time, low sensitivity, and poor selectivity, and achieve the effects of strong anti-interference ability, high selectivity, and high selectivity

Active Publication Date: 2021-03-09
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, the reported methods for detecting formaldehyde include spectrophotometric colorimetry, high performance liquid chromatography, chemiluminescence analysis, photochemical sensing, etc., but these methods are complicated and cannot detect formaldehyde in vivo, so fluorescent probes It has become the focus of researchers because of its unique advantages such as high selection, ultra-sensitivity, and simple synthesis.
There are still some defects in the reported fluorescent probe analysis methods, such as low sensitivity, poor selectivity, complex synthesis, long response time, etc. Other active carbonyl substances in the living body are similar to formaldehyde, which will pose a potential problem for the detection of formaldehyde. interference, and the currently reported fluorescent probes cannot distinguish between endogenous and exogenous formaldehyde. Therefore, the development of fast, highly sensitive and highly selective fluorescent probes, especially the ability to distinguish between endogenous and exogenous formaldehyde Fluorescent probes have become an urgent problem for those skilled in the art

Method used

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  • Novel cell membrane specific formaldehyde fluorescent probe as well as preparation method and application thereof
  • Novel cell membrane specific formaldehyde fluorescent probe as well as preparation method and application thereof
  • Novel cell membrane specific formaldehyde fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of formula (II) compound

[0052] The synthetic design route is as follows:

[0053]

Embodiment approach 1

[0054] Embodiment 1: Dissolve 399 mg (1 mmol) of naphthalimide compound (IV) in 10 mL of ethylene glycol methyl ether, then add 0.5 mL of hydrazine hydrate and reflux for 4 hours. After the reaction is complete, cool at room temperature to precipitate a solid, and then filter with suction A solid was obtained, and the crude product was further subjected to chromatographic column separation using dichloromethane as the eluent to obtain a pure product. About 253 mg of pure product was obtained, the yield was 64%.

Embodiment approach 2

[0055] Embodiment 2: 399 mg (1 mmol) of naphthalimide compound (IV) was dissolved in 10 mL of ethylene glycol methyl ether, and then 1 mL of hydrazine hydrate was added to reflux for 4 hours. After the reaction was completed, solids were precipitated by cooling at room temperature, and then suction filtered to obtain solid, and the crude product was further subjected to chromatographic column separation with dichloromethane as the eluent to obtain pure product. About 253 mg of pure product was obtained, the yield was 64%.

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Abstract

The invention relates to a novel cell membrane specific fluorescent probe as well as a preparation method and application thereof; particularly, the novel cell membrane specific fluorescent probe canbe used for measuring, detecting or screening formaldehyde and living cell fluorescence imaging, and particularly can be applied to distinguishing and detecting endogenous formaldehyde and exogenous formaldehyde and imaging. The probe can realize at least one of the following technical effects: targeting and positioning cell membranes, distinguishing and detecting endogenous formaldehyde and exogenous formaldehyde, identifying formaldehyde with high selectivity, quickly responding to formaldehyde, sensitively analyzing formaldehyde, detecting formaldehyde under physiological level conditions,and being simple to synthesize and stable in property.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a formaldehyde fluorescent probe based on naphthalimide compounds and its application in measuring, detecting or screening formaldehyde and live cell fluorescence imaging methods; the invention also provides the prepared Methods for fluorescent probes. Background technique [0002] Formaldehyde is the simplest aldehyde substance and a typical active carbonyl substance; formaldehyde is also one of the important raw materials for the industrial production of urea-formaldehyde resin and phenolic resin, and is extremely important for the clothing textile industry and furniture manufacturing industry. At the same time, formaldehyde is also used in the production of disinfectants, preservatives, pesticides and other industries. At this stage, the human demand for formaldehyde is still very large. [0003] Formaldehyde has long been recognized as a human toxin and carcinogen, release...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6428C09K2211/1029G01N2021/6417
Inventor 蔡昕宇曲乐扬高娜彭艺媛王梦琪张雪柳彩云白健朱宝存
Owner UNIV OF JINAN
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