Amino-substituted chromene quinoline type fluorescent marker as well as preparation and application thereof

Abstract

The invention belongs to the technical field of fluorescence labeling, and particularly relates to an amino-substituted chromene quinoline type fluorescence marker as well as preparation and application thereof. According to the invention, amino groups of aromatic amine compounds and two ortho-chlorine-containing aldehyde coumarins are subjected to a one-step cyclization reaction to obtain a series of novel nitrogen-containing heterocyclic compounds. The compound has excellent fluorescence emission performance and also has good light stability in different organic solvents. According to the invention, the problem of poor light stability of cyanine dyes is effectively solved, and different organelles can be marked at the cellular level. The nitrogen heterocyclic ring is introduced, so that the biocompatibility of the compound is improved, and a good foundation is laid for biological application. Besides, the raw materials of the reaction are cheap and easy to obtain, the steps for synthesizing the marker are simple and easy to operate, the production cost can be effectively reduced while the performance of the marker is not reduced, and certain commercial value is achieved.

Description

technical field [0001] The invention belongs to fluorescent labeling technology, in particular to an amino-substituted chromenoquinoline fluorescent label and its preparation and application. Background technique [0002] As a dynamic independent organelle, lipid droplet is an important place for neutral lipid storage in eukaryotic cells. In the process of lipid coordination, it can promote the absorption, metabolism, transportation and signal transduction of lipids in cells, and then maintain The smooth progress of various physiological activities (reference: J.-W.Shi, Y.Tian, ​​X.-L.Zhang, et al., An AIEgen-Based Fluorescent Probe for Highly Selective and Specific Imaging of Lipid Dropletsin L02 and HepG2 Cells ,Sensors and Actuators B:Chemical,2019(284)545-552); Mitochondria are composed of a double-membrane system and are organelles involved in energy metabolism and cellular homeostasis in eukaryotic cells, so they act as energy in the activities of the entire living bod...

AI Technical Summary

Problems solved by technology

[0003] After long-term and repeated use of the commonly used cell organelle markers, some shortcomings gradually emerged

Derivatives of Nile Red and BODIPY are commonly used commercial lipid droplet markers, and Nile Red derivatives lack specificity for lipid droplets during the labeling process, and in some cases will stain other organelles; BODIPY derivatives are due to The relatively small Stokes shift also limits its use

In the process of labeling mitochondria, most of the commonly used commercial markers are some salt structures, such as triphenylphosphine salt, pyridinium salt and indole salt, etc. They can be located in mitochondria, but there are also some problems. These cations enter the cell Afterwards, it will change the membrane potential of mitochondria, thereby changing the microenvironment of cells and affecting the physiological activities of living organisms (reference: Y.Wang, B.Xu, R.Sun, J.-F.Ge, et al., TheApplication of Nitrogen Heterocycles in Mitochondrial-Targeting FluorescentMarkers with Neutral Skeletons, J.Mater.Chem.B,2020(8)7466)

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