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A kind of pyridine sulfonic acid inner salt compound and its preparation method and application

A pyridine sulfonic acid and compound technology, which is applied in the field of infrared fluorescent probes and their preparation, and achieves the effects of mild reaction conditions, little damage to cells and tissues, and low cost

Active Publication Date: 2021-02-09
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Infrared fluorescent probes with good biocompatibility and the ability to specifically label nerve cells are rarely reported, and are urgently needed to be explored

Method used

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  • A kind of pyridine sulfonic acid inner salt compound and its preparation method and application
  • A kind of pyridine sulfonic acid inner salt compound and its preparation method and application
  • A kind of pyridine sulfonic acid inner salt compound and its preparation method and application

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Embodiment Construction

[0022] 1. Synthesis of SL-Neu

[0023] Dissolve 4-(bis(2-hydroxyethyl)amino)benzaldehyde (1.80g, 10mmol), 4-methyl-1-(3-sulfopropyl)pyridinium (2.15g, 10mmol) in 30mL In absolute ethanol, 5 drops of piperidine was added dropwise to the reaction system, stirred until reflux for 24 hours, a red solid was precipitated, filtered by suction, washed with ethanol to obtain red crystal SL-Neu (3.40 g), yield 87 %.

[0024] SL-Neu: 1 H NMR (400MHz, d 6 -DMSO) δ8.76(d, J=6.3Hz, 2H), 8.04(d, J=6.2Hz, 2H), 7.90(d, J=16.1Hz, 1H), 7.56(d, J=8.4Hz, 2H), 7.14(d, J=16.0Hz, 1H), 6.79(d, J=8.4Hz, 2H), 4.83(s, 2H), 4.54(t, J=6.6Hz, 2H), 3.72–3.46( m,8H),2.43(t,J=7.0Hz,2H),2.26–2.10(m,2H). 13 C NMR (100MHz, d 6 -DMSO) δ=153.64, 150.27, 143.53, 142.10, 130.38, 122.21, 121.97, 116.59, 111.47, 58.18, 57.89, 53.77, 47.05, 38.65, 27.11. 19 h 24 N 2 o 4 S: C, 60.62; H, 6.43; N, 7.44%.Found: C, 60.85; H, 6.618; N, 7.455%.IR(KBr, cm -1 ):3371(m),3045(m),2905(m),2871(m),1643(m),1589(s),1524(s),1...

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Abstract

The invention discloses a pyridinesulfonic acid inner salt compound and its preparation method and application, wherein the structural formula of the pyridinesulfonic acid inner salt compound is: the present invention adopts 4‑(bis(2 -Hydroxyethyl)amino)benzaldehyde reacts with 4-methyl-1-(3-sulfopropyl)pyridinium to prepare D-π-A co- Confocal laser imaging of pyridinesulfonic acid inner salt compound SL‑Neu with conjugated structure was performed using mouse brain tissue and its vertebral tissue as materials. The results show that SL‑Neu can specifically label nerve cells distributed in mice (cerebellum, midbrain, gyrus, hippocampus, spine), and can be used as a near-infrared fluorescent probe for specifically labeling nerve cells.

Description

technical field [0001] The invention relates to an infrared fluorescent probe and its preparation method, in particular to a pyridine sulfonic acid inner salt compound, its preparation method and application. Background technique [0002] Nerve cells (Neuron) are the structural and functional units of the nervous system of higher animals, also known as neurons. The nervous system contains a large number of neurons. It is estimated that there are about 100 billion neurons in the human central nervous system, and there are about 14 billion neurons in the cerebral cortex alone. A large number of nerve cells gather in the brain to play the role of receiving, integrating, transmitting and outputting information. The neuron population realizes the cognitive and analytical functions of the brain through the information exchange of each neuron. In recent years, more and more studies have shown that the structure and function of nerve cells are closely related to some central nervou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/38C09K11/06A61K49/00
CPCA61K49/0021C07D213/38C09K11/06C09K2211/1007C09K2211/1029
Inventor 吴杰颖方斌刘天妍田肖和赵燕倩王一文李虎田玉鹏
Owner ANHUI UNIVERSITY