Synthesis and Application of Fluorescent Probes for Multi-Type Organelles Containing Heteroatom Polycyclic Aromatic Hydrocarbons

A polycyclic aromatic hydrocarbon and heteroatom technology, applied in the field of synthesis of heteroatom-doped polycyclic aromatic hydrocarbon fluorescent probes, can solve the problems of cumbersome synthetic routes, low atom/step economy, low yield, etc., and achieve photostability Good, good biocompatibility, simple synthetic route

Active Publication Date: 2022-06-07
SICHUAN UNIV
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  • 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 Fluorescent Probes for Multi-Type Organelles Containing Heteroatom Polycyclic Aromatic Hydrocarbons
  • Synthesis and Application of Fluorescent Probes for Multi-Type Organelles Containing Heteroatom Polycyclic Aromatic Hydrocarbons
  • Synthesis and Application of Fluorescent Probes for Multi-Type Organelles Containing Heteroatom Polycyclic Aromatic Hydrocarbons

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0053] (1) Acridone (39.1 mg, 0.20 mmol), diphenylacetylene (71.2 mg, 0.40 mmol), [Cp*RhCl 2 ] 2 (3.1 mg, 5 μmol, 2.5 mol%), AgOAc (66.8 mg, 0.40 mmol), 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, filter through celite and wash with 10 to 20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The compound was separated and purified by silica gel column chromatography (dichloromethane / ethyl acetate=15:1, v / v), and the target product 2,3-diphenylpyran[4,3,2 was obtained after vacuum drying. -kl]acridine 7-onium hexafluoroantimonate (I-a)...

Embodiment 2

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

[0056] (1) Acridone (39.1 mg, 0.20 mmol), diphenylacetylene (71.2 mg, 0.40 mmol), [Cp*RhCl 2 ] 2 (3.1 mg, 5 μmol, 2.5 mol%), AgOAc (66.8 mg, 0.40 mmol), 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, filter through celite and wash with 10 to 20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The compound was separated and purified by neutral alumina column chromatography (dichloromethane / ethyl acetate=10:1, v / v), and the target product 2,3-diphenylpyran was obtained after vacuum drying. 4,3,2-kl]acridine (II-a) 55.7 mg, yield 75%. 1 H NMR (400MHz, CD 2 Cl 2 )...

Embodiment 3

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

[0059] (1) N-methylacridone (41.8mg, 0.20mmol), diphenylacetylene (71.2mg, 0.40mmol), [Cp*RhCl 2 ] 2 (3.1 mg, 5 μmol, 2.5 mol%), AgOAc (66.8 mg, 0.40 mmol), 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, filter through celite and wash with 10 to 20 mL of dichloromethane, combine the filtrates, remove the solvent under reduced pressure, and the remaining The compound was separated and purified by silica gel column chromatography (dichloromethane / ethyl acetate=20:1, v / v), and the target product 2,3-diphenyl-7-methyl-7H- Pyran[4,3,2-kl]acridine-1-onium hexafluoroantimonate (III-a)...

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Abstract

The invention relates to the synthesis and application of a multi-type organelle fluorescent probe containing heteroatom polycyclic aromatic hydrocarbons. The fluorescent probe of the present invention can specifically target lysosomes, endoplasmic reticulum, mitochondria, and mitochondria-nucleus, and is applied to fluorescence imaging, labeling, tracing and biological treatment. The synthesis method of the invention is to activate C=X (X=N, O, S, N-R) and alkynes to undergo [4+2] oxidative cyclization reaction through rhodium-catalyzed activation. In this method, heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) derivatives with diverse structures are efficiently and rapidly synthesized from cheap and readily available acridones and their analogs. Compared with the traditional reaction system, this method not only achieves high-throughput and rapid synthesis of various heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) derivatives, but also has the advantages of simple operation, mild conditions, and low cost; at the same time, through this The method can quickly establish a library of powerful fluorescent functional molecules, which has great potential commercial value.

Description

technical field [0001] The invention relates to the synthesis and application of four types of heteroatom-doped polycyclic aromatic hydrocarbon fluorescent probes with specific targeting to multiple types of organelles. Background technique [0002] With the vigorous development of life sciences, people's research on subcellular organelles continues to deepen. As the main organelles of eukaryotic cells, lysosomes, endoplasmic reticulum, mitochondria and nucleus undertake necessary and important life activities. As the "digestive organ" of organelles, lysosomes contain a variety of acidic hydrolase enzymes to maintain the pH value of the internal environment within 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 abnormal quantity and distribution may cause various diseases such as lung diseases, lysosomal storage diseases and tumors. [...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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