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Synthesis and application of heteroatom polycyclic aromatic hydrocarbon-containing multi-type organelle fluorescent probe

A technology of polycyclic aromatic hydrocarbons and fluorescent probes, which is applied in the direction of fluorescence/phosphorescence, instruments, and luminescent materials, etc. It can solve the problems of cumbersome synthesis routes, low yields, low atom/step economy, etc., and achieve good photostability , The synthesis route is simple, and the effect of biocompatibility is good

Active Publication Date: 2020-12-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the traditional preparation methods of heteroatom-doped polycyclic skeleton PAHs usually go through tedious synthetic routes and are prepared under harsh reaction conditions, but the final yield is not high and the atom / step economy is low. The desire to make the diversity of the molecular framework is very limited

Method used

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  • Synthesis and application of heteroatom polycyclic aromatic hydrocarbon-containing multi-type organelle fluorescent probe
  • Synthesis and application of heteroatom polycyclic aromatic hydrocarbon-containing multi-type organelle fluorescent probe
  • Synthesis and application of heteroatom polycyclic aromatic hydrocarbon-containing multi-type organelle fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Synthesis of 2,3-diphenylpyrano[4,3,2-kl]acridinium 7-ium hexafluoroantimonate (I-a)

[0053] (1) Add acridone (39.1mg, 0.20mmol), toluene (71.2mg, 0.40mmol), [Cp*RhCl 2 ] 2 (3.1mg, 5μmol, 2.5mol%), AgOAc (66.8mg, 0.40mmol), AgSbF 6 (13.7mg, 40μmol, 20mol%), NaSbF 6 (51.7mg, 0.20mmol) and tetrahydrofuran (1.0mL) were added to the reaction tube, stirred evenly, heated to 80°C, and reacted for 10 hours;

[0054] (2) After the reaction is completed, cool the reaction tube to room temperature, add 10 mL of dichloromethane to dilute the reaction system, then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The product was separated and purified by silica gel column chromatography (dichloromethane / ethyl acetate=15:1, v / v), and after vacuum drying, the target product 2,3-diphenylpyran[4,3,2 -kl] Acridinium 7-ium hexafluoroantimonate (I-a) 81.3 mg, yiel...

Embodiment 2

[0055] Embodiment 2: Synthesis of 2,3-diphenylpyrano[4,3,2-kl]acridine (II-a)

[0056] (1) Add acridone (39.1mg, 0.20mmol), toluene (71.2mg, 0.40mmol), [Cp*RhCl 2 ] 2 (3.1mg, 5μmol, 2.5mol%), AgOAc (66.8mg, 0.40mmol), AgSbF 6 (13.7mg, 40μmol, 20mol%), NaSbF 6 (51.7mg, 0.20mmol) and tetrahydrofuran (1.0mL) were added to the reaction tube, stirred evenly, heated to 80°C, and reacted for 10 hours;

[0057] (2) After the reaction is completed, cool the reaction tube to room temperature, add 10 mL of dichloromethane to dilute the reaction system, then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The product was separated and purified by neutral aluminum oxide column chromatography (dichloromethane / ethyl acetate=10:1, v / v), and after vacuum drying, the target product 2,3-diphenylpyran[ 4,3,2-kl] acridine (II-a) 55.7 mg, yield 75%. 1 H NMR (400MHz, CD 2 Cl 2 ):δ=...

Embodiment 3

[0058] Example 3: Synthesis of 2,3-diphenyl-7-methyl-7H-pyrano[4,3,2-kl]acridin-1-ium hexafluoroantimonate (III-a)

[0059] (1) Mix N-methylacridone (41.8mg, 0.20mmol), toluene (71.2mg, 0.40mmol), [Cp*RhCl 2 ] 2 (3.1mg, 5μmol, 2.5mol%), AgOAc (66.8mg, 0.40mmol), AgSbF 6 (13.7mg, 40μmol, 20mol%), NaSbF 6 (51.7mg, 0.20mmol) and tetrahydrofuran (1.0mL) were added to the reaction tube, stirred evenly, heated to 80°C, and reacted for 10 hours;

[0060] (2) After the reaction is completed, cool the reaction tube to room temperature, add 10 mL of dichloromethane to dilute the reaction system, then filter through diatomaceous earth and wash with 10-20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The product was separated and purified by silica gel column chromatography (dichloromethane / ethyl acetate=20:1, v / v), and after vacuum drying, the target product 2,3-diphenyl-7-methyl-7H- Pyran[4,3,2-kl]acridin-1-ium hexafluoroa...

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Abstract

The invention relates to synthesis and application of a heteroatom polycyclic aromatic hydrocarbon-containing multi-type organelle fluorescent probe. The fluorescent probe disclosed by the invention can be used for specifically targeting lysosome, endoplasmic reticulum, mitochondria and mitochondrial cell nucleus, and is applied to fluorescence imaging, labeling, tracing and biological treatment.According to the synthesis method, rhodium catalytically activated C=X (X is N, O, S, NR) and alkyne are subjected to [4+2] oxidative cyclization reaction, and the heteroatom-doped polycyclic aromatichydrocarbon (PAHs) derivative with various structures is efficiently and rapidly synthesized by utilizing acridone and analogues thereof which are cheap and easy to obtain. Compared with a traditional reaction system, the method not only realizes high-throughput rapid synthesis of various heteroatom doped polycyclic aromatic hydrocarbon (PAHs) derivatives, but also has the advantages of simple and convenient operation, mild conditions, low cost and the like, can rapidly establish a fluorescent functional molecular library with powerful functions, and has huge potential commercial value.

Description

technical field [0001] The present invention relates to the synthesis and application of four types of heteroatom-doped polycyclic aromatic hydrocarbon fluorescent probes with specific targeting multi-type organelles. Background technique [0002] With the vigorous development of life science disciplines, people's research on subcellular organelles continues to deepen. As the main organelles of eukaryotic cells, lysosome, endoplasmic reticulum, mitochondria and nucleus undertake necessary and important life activities. Lysosome is the "digestive organ" of the cell organelle, and the various acid hydrolytic enzymes contained in the lysosome keep the pH value of the internal environment in the range of 4.5-5.0. As an important acidic organelle in eukaryotic cells, lysosomes have important functions of intracellular digestion and regulation of secretion. At the same time, its quantity and distribution are abnormal, which may cause various diseases such as lung diseases, lysos...

Claims

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Application Information

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IPC IPC(8): C07D491/06C09K11/06G01N21/64A61K49/00
CPCC07D491/06C09K11/06G01N21/6428G01N21/6458A61K49/0026C09K2211/1029C09K2211/1007
Inventor 游劲松马蔚欣
Owner SICHUAN UNIV
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