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A nucleic acid fluorescent probe for nuclear staining and its preparation method

A fluorescent probe and cell nucleus technology, applied in the field of cell nucleus fluorescent probes, can solve the problems of high biological toxicity and low anti-biological metabolism ability, and achieve the effects of strong resistance to enzymolysis, good fluorescent properties, and low cytotoxicity

Active Publication Date: 2020-03-31
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the solution state, these fluorescent dyes usually face problems such as easy photobleaching, high biological toxicity, and low ability to resist biological metabolism.

Method used

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  • A nucleic acid fluorescent probe for nuclear staining and its preparation method
  • A nucleic acid fluorescent probe for nuclear staining and its preparation method
  • A nucleic acid fluorescent probe for nuclear staining and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A, the preparation of intermediate 1

[0030] At room temperature, dissolve 1.26mmol 6-amino-2-methylquinoline in acetonitrile and add it to a 250ml flask, then slowly add 1.33mmol N-bromosuccinimide and a catalytic amount of silica gel, and continue stirring for 15min Afterwards, the liquid in the bottle turned dark brown, and thin-layer chromatography determined that new spots were generated in the reaction, and the raw materials were not completely reacted, and the reaction was continued for 12 hours. After the reaction was finished, extracted with ethyl acetate, spin-dried the solvent, and the residue was separated and purified through a chromatographic column (ethyl acetate:petroleum ether volume ratio=1:6) to obtain 207 mg of a yellow solid product, namely intermediate 1, with a yield of 69%.

[0031] 1 H NMR (400MHz, CDCl3, TMS): δ = 8.23 ​​(d, J = 8.6Hz, quinoline-H, 1H), 7.81 (d, J = 9.0Hz, quinoline-H, 1H), 7.28 (d, J = 8.6Hz, quinoline-H, 1H), 7.20 (d, J=9...

Embodiment 2

[0045] A, the preparation of intermediate 1

[0046] At room temperature, dissolve 1.26mmol 6-amino-2-methylquinoline in acetonitrile and add it to a 250ml flask, then slowly add 1.33mmol N-bromosuccinimide and a catalytic amount of silica gel, and continue stirring for 15min Afterwards, the liquid in the bottle turned dark brown, and thin-layer chromatography determined that new spots were generated in the reaction, and the raw materials were not completely reacted, and the reaction was continued for 16 hours. After the reaction was finished, extracted with ethyl acetate, spin-dried the solvent, and the residue was separated and purified by chromatographic column (ethyl acetate:petroleum ether volume ratio=1:6) to obtain 222 mg of a yellow solid product, namely intermediate 1, the yield was 74%.

[0047] B, the preparation of intermediate 2

[0048] Add 90mg of intermediate 1 to a round bottom flask, dissolve it in 16ml of a mixed solution of water:ethanol:toluene at a volu...

Embodiment 3

[0052] A, the preparation of intermediate 1

[0053] At room temperature, dissolve 1.26mmol 6-amino-2-methylquinoline in acetonitrile and add it to a 250ml flask, then slowly add 1.33mmol N-bromosuccinimide and a catalytic amount of silica gel, and continue stirring for 15min Afterwards, the liquid in the bottle turned dark brown, and thin-layer chromatography determined that new spots were generated in the reaction, and the raw materials were not completely reacted, and the reaction was continued for 18 hours. After the reaction, extract with ethyl acetate, spin to dry the solvent, and the residue is separated and purified by chromatographic column (ethyl acetate:petroleum ether volume ratio=1:6) to obtain 216 mg of a yellow solid product, namely intermediate 1, the yield was 72%.

[0054] B, the preparation of intermediate 2

[0055] Add 90mg of intermediate 1 to a round bottom flask, dissolve it in 16ml of a mixed solution of water:ethanol:toluene at a volume ratio of 3:3...

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Abstract

The invention discloses a preparation method of a nucleic acid fluorescence probe compound AzosD for nuclear staining. The preparation method is characterized by comprising steps as follows: 6-amino-2-methylquinoline is dissolved in acetonitrile, N-bromosuccinimide is added, a reaction is performed, and an intermediate 1 is obtained; the intermediate 1 is dissolved in a water, ethanol and toluenemixed solution, 3-(N,N-dimethylamino)phenylboronic acid, tetrakis(triphenylphosphine)palladium and sodium carbonate are added, refluxing reaction is performed under nitrogen protection, and an intermediate 2 is obtained; the intermediate 2 is dissolved by hydrochloric acid, sodium nitrite is added to the solution under the condition of ice-water bath, pH of the solution is regulated to be neutralby a sodium hydroxide aqueous solution, and 3-methyl-11-(N,N-dimethylamino) cinnoline[3,4-e]quinoline, namely AzosD, is obtained by separation and purification. The compound is good in photobleachingresistant effect, high in biocompatibility, high in enzyme-resistant capacity and high in nuclear targeting, can be applied to specific staining of nucleuses of living cells, and has broad applicationprospect in the fields of long-term monitoring of nuclear morphometry and observation for nuclear morphology change in the cellular physiological process.

Description

technical field [0001] The invention belongs to the technical field of cell nucleus fluorescent probes, in particular to a nucleic acid fluorescent probe 3-methyl-11-(N,N-dimethylamino)cinnolino[3,4-e]quinone used for cell nucleus staining Phenyl (AzosD) and its preparation method. Background technique [0002] With the development of science and technology, human beings have a deeper understanding of the nucleus. The nucleus is the largest and most important organelle in eukaryotic cells, and it is the regulatory center of cell inheritance and metabolism. The nucleus is the control center of the cell, plays an important role in the metabolism, growth and differentiation of the cell, and is the main location of genetic material. Nucleic acid is a biological macromolecule closely related to life activities and diseases. Therefore, the staining, tracking and morphological observation of the nucleus are of great significance for understanding the life process of the whole ce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06C09K2211/1029C09K2211/1044G01N21/6428
Inventor 宋钦华李琛
Owner UNIV OF SCI & TECH OF CHINA
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