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A ratiometric fluorescent probe and its preparation method and application

A reaction, molar ratio technique, applied in the field of biochemistry

Active Publication Date: 2022-03-04
潍坊千宏企业管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the design of ratiometric fluorescent probes for nucleic acid responses is facing great challenges, which not only require the probes to have good membrane permeability and low cytotoxicity, but more importantly, this requires the probes to be selective for nucleic acids. Ratiometric fluorescence response, and probes with appropriate excitation / emission wavelengths
There are currently no suitable ratiometric fluorescent probes for the detection of nucleic acid content in living cells and tissue sections

Method used

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  • A ratiometric fluorescent probe and its preparation method and application
  • A ratiometric fluorescent probe and its preparation method and application
  • A ratiometric fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1, 2-(4-(diethylamino)styryl)-1-methyl-7-(4-(4-pyridyl)-1-piperazinyl)quinoline-1-iodide ( Preparation of QPP-AS)

[0083] The synthetic route of QPP-AS is as follows Figure 19 Shown:

[0084] (1) Dissolve 7-chloro-2-methylquinoline (compound 1-1) (10mmol, 1.77g) in 30mL acetonitrile, add iodomethane (100mmol, 14.2g) to obtain a reaction solution, and place the reaction solution in In the condensing reflux device, control the temperature at 42.5°C, stir and react for 24 hours, cool down, the solid precipitates out in the reaction system, filter, wash the precipitate with acetonitrile 5 times, and dry the obtained precipitate in vacuum to obtain compound 2-1 (white solid, 2.64 g, 73% yield).

[0085] (2) 7-chloro-1,2-dimethylquinolin-1-ium iodide (compound 2-1) (2mmol, 0.636g) and 1-(4-pyridyl)piperazine (compound 3- 1) The mixture (2.1mmol, 0.342g) was placed in 20mL 1-butanol to obtain a reaction liquid, which was placed in a condensation reflux reaction d...

Embodiment 2

[0086] Example 2, 2-(4-(diethylamino)styryl)-1-methyl-7-(4-methyl-1-piperazinyl)quinoline-1-iodide (QMP-AS) preparation of

[0087] The synthetic route of QMP-AS is as follows: Figure 20 Shown:

[0088] (1) Dissolve 7-chloro-2-methylquinoline (compound 1-1) (10mmol, 1.77g) in 30mL acetonitrile, add iodomethane (100mmol, 14.2g) to obtain a reaction solution, and place the reaction solution in In the condensing reflux device, control the temperature at 42.5 ° C, stir and react for 24 hours, cool down, the solid precipitates in the reaction system, filter, wash the precipitate with acetonitrile for 5 times, and dry the obtained precipitate in vacuum to obtain compound 2-1 (white solid, 2.64 g, 73% yield).

[0089](2) 7-chloro-1,2-dimethylquinolin-1-ium iodide, (compound 2-1) (2mmol, 0.636g) and 1-methylpiperazine (compound 3-2) ( 2.1mmol, 0.210g) of the mixture was placed in 20mL 1-butanol to obtain a reaction solution, which was placed in a condensation reflux reaction devi...

Embodiment 3

[0090] Example 3, 1-methyl-2-(4-(4-methyl-1-piperazinyl) styryl)-7-(4-(4-pyridyl)-1-piperazinyl)quinone Preparation of phenoline-1-iodide (QPP-PS)

[0091] The synthetic route of QPP-PS is as follows: Figure 21 Shown:

[0092] (1) Dissolve 7-chloro-2-methylquinoline (compound 1-1) (10mmol, 1.77g) in 30mL acetonitrile, add iodomethane (100mmol, 14.2g) to obtain a reaction solution, and place the reaction solution in In the condensing reflux device, control the temperature at 42.5°C, stir and react for 24 hours, cool down, the solid precipitates out in the reaction system, filter, wash the precipitate with acetonitrile 5 times, and dry the obtained precipitate in vacuum to obtain compound 2-1 (white solid, 2.64 g, 73% yield).

[0093] (2) 7-chloro-1,2-dimethylquinolin-1-ium iodide, (compound 2-1) (2mmol, 0.636g) and 1-(4-pyridyl) piperazine, (compound 3-1) The mixture of (2.1mmol, 0.342g) was placed in 20mL 1-butanol to prepare a reaction solution, and the reaction solution...

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Abstract

The invention relates to the technical field of biochemistry, and discloses a ratiometric fluorescent probe and its preparation method and application. The general formula of the ratiometric fluorescent probe is shown in formula (1): in the formula, R 1 is methyl, R 2 selected from 4-picoline, methyl, R 3 Selected from N,N-diethyl, 4-methylpiperazine, X is halogen. The probe has a selective ratiometric fluorescence response to nucleic acid and has ideal biocompatibility. Using this probe, the in situ real-time ratiometric fluorescence imaging of nucleic acid has been realized for the first time in living cells, and the mitotic interphase of living cells has been successfully monitored. Nucleic acid changes, as well as chromatin aggregation and separation in apoptotic cells; ratiometric fluorescence imaging of nucleic acids in tissue sections with this probe can obtain detailed information on nucleic acid content and distribution.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to a ratio-type fluorescent probe and its preparation method and application. Background technique [0002] Nucleic acid (DNA / RNA) is the main material basis for storing and transmitting genetic information. The distribution and behavior of nucleic acids is an important dynamic process closely related to the normal function of cells. Dysregulation of nucleic acid behavior can lead to cellular dysfunction and induce various diseases, such as cancer and Parkinson's disease. Tracking the dynamic changes of nucleic acids in living cells is of great significance for understanding the relationship between the dynamic behavior and functions of nucleic acids in different biological processes. For example, tracking the nucleic acid replication process can determine the different stages of cell mitosis and monitor changes in cell division behavior; tracking the distribution...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D215/38C09K11/06G01N21/64
Inventor 王康男潘琦玲李文娟
Owner 潍坊千宏企业管理有限公司
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