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Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye

A technology of nitrobenzimidazole and fluorescent dyes, which is applied in the field of fluorescent dyes, can solve the problems of low phototoxicity, biological toxicity, photobleaching, high phototoxicity, and poor photostability, and achieve good cell membrane permeability, High selectivity and good specificity

Active Publication Date: 2014-04-09
SICHUAN ANKERUI NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to propose a fluorescent dye using nitrobenzimidazole as an RNA recognition group in view of the defects of high phototoxicity, poor photostability and poor specificity in the above-mentioned existing RNA analysis technology. It has efficient and specific recognition ability for RNA, and also has efficient two-photon absorption ability, and has low phototoxicity, biological toxicity and photobleaching

Method used

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  • Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye
  • Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye
  • Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye

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preparation example Construction

[0061] The preparation method of the fluorescent dye using nitrobenzimidazole as the RNA recognition group comprises the following steps: reacting the parent body of D with 6-nitrobenzimidazole in a molar ratio of 1:1-1:5, and reacting The temperature is 25-150°C, the reaction time is 6-48 hours, the reaction solvent is one or more of dichloromethane, ethanol and ethyl acetate, and the reaction is carried out in the presence of an organic base, with 4-dimethylamino Pyridine is the catalyst.

[0062] The fluorescent dye with nitrobenzimidazole as the RNA recognition group is a compound of general formula V, and the preparation method of the compound of general formula V comprises the following steps:

[0063]

[0064] (1), ethanolamine and concentrated hydrobromic acid according to the literature (AndrewF, DianaF, KarenLG.Drugs.1992.43(4):561:) to prepare the compound of general formula VIII

[0065]

[0066] (2), the preparation of the compound of general formula VI com...

Embodiment 1

[0090] Prepare fluorescent probe BIQ:

[0091]

[0092] (1) Synthesis of compounds of general formula VIII

[0093] Ethanolamine (122.2g, 120.8mL, 2.0mol) was added dropwise to concentrated hydrobromic acid (733mL, 5.4mol) under stirring at 10°C, and the temperature was controlled at 10-15°C. After dropping, continue stirring for 1h, and then add 400mL of xylene , warming up to reflux, and after separating about 515mL of water (containing a small amount of hydrobromic acid) with a water separator, the water pump decompresses to evaporate xylene and excess hydrobromic acid. Cool the solution to about 70%, add ice-cold (usually about 4°C) acetone (365mL), stir the mixture fully, so that the dark-colored solid is fully soaked, cool, suction filter, and cool (usually about 4°C) ) washed with acetone (150mL), sucked dry, and dried to obtain a white crystalline product of the compound of general formula VIII, weighing 358.8g, yield 87.6%, M.P.173-175°C.

[0094] (2) Synthesis o...

Embodiment 2

[0136] Preparation of Fluorescent Probe IX

[0137]

[0138] (1) Synthesis of compounds of general formula X

[0139] Dissolve 10mmol of p-fluorobenzaldehyde and 10mmol of 6-nitrobenzimidazole in 20ml of dry DMF (dimethyl fumarate), add a small amount of potassium carbonate (catalyst) to the mixture each time, and The total amount of potassium was 12 mmol, and the addition was completed within 15 minutes. Reacted under stirring at 110°C for 10-12h. After the reaction was completed, the reaction system was cooled to room temperature, filtered with suction, and the filtrate was extracted with ethyl acetate. The organic phase was washed 3 times with water, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. The product was separated by column chromatography.

[0140] (2) Synthesis of fluorescent dye with nitrobenzimidazole as RNA recognition group (referred to as fluorescent probe IX)

[0141] Put 0.85mmol of the intermediate compound of general formul...

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Abstract

The invention provides a fluorescent dye with nitrobenzimidazole as an RNA (ribonucleic acid) recognition group as well as a preparation method and application of the fluorescent dye. The fluorescent dye with the nitrobenzimidazole as the RNA recognition group has the structure represented by the general formula I, wherein D is a chromophoric group of the dye; the parent of D is selected from a naphthalimide dye, an essence dye, a rhodamine dye, a fluorescein dye, an anthracene pyridine dye or a perylene bisimide dye. The invention also provides application of the fluorescent dye with the nitrobenzimidazole as the RNA recognition group in specific RNA labeling in a biological sample. The fluorescent dye disclosed by the invention has high-efficiency and specific RNA recognition capacity and also has high-efficiency two-photon absorption capacity; furthermore, the fluorescent dye is low in photoinduced toxicity, biological toxicity and light bleaching performance.

Description

technical field [0001] The invention relates to fluorescent dye technology, in particular to a fluorescent dye using nitrobenzimidazole as an RNA recognition group, its preparation method and application. Background technique [0002] Ribonucleic acid (Ribonucleic acid, abbreviated as RNA) is an important biomacromolecule, named after the molecule is composed of ribonucleotides. Each RNA molecule is made up of long chains of nucleotide units, each containing a nitrogenous base, a ribose sugar, and a phosphate group. RNA is an intermediate carrier of genetic information in organisms with a cellular structure, and is involved in protein synthesis; it is also involved in the regulation of gene expression. For some viruses, RNA is the only genetic material. RNA exists in the cytoplasm and nucleus of all cells, and also exists in most known plant viruses, some animal viruses and some bacteriophages. [0003] RNA is a long chain molecule formed by condensation of ribonucleotide...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/06C07D403/14C07D405/10C09B57/00G01N21/64C12Q1/68
Inventor 彭孝军张双喆樊江莉王静云仉华
Owner SICHUAN ANKERUI NEW MATERIAL CO LTD
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