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RNA fluorescent probe and manufacturing method and application thereof

A fluorescent probe and reaction technology, which is applied in the detection of RNA and nucleolus imaging in cells, can solve the problems affecting the application value, slow response speed, and high phototoxicity, and achieve low biological toxicity, good membrane permeability, and light The effect of strong stability

Active Publication Date: 2016-11-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This fluorescent probe has some defects in practical imaging applications, such as slow response to RNA, high phototoxicity and poor photostability, which affect its application value

Method used

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  • RNA fluorescent probe and manufacturing method and application thereof
  • RNA fluorescent probe and manufacturing method and application thereof
  • RNA fluorescent probe and manufacturing method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment one: the synthesis of compound 2

[0028] Weigh 0.2g (1.1236mmol) of 4-chloro-quinaldine into a 25ml round-bottomed flask, add about 0.96g of iodomethane and 1.5ml of sulfolane in 6 times the molar amount, heat the mixture to 50°C, and react for 18 hours , cooled, shaken after adding anhydrous diethyl ether, suction filtered, the solid was washed with anhydrous diethyl ether, weighed after vacuum drying to obtain 0.345g of compound 2 with a yield of 95.8%: 1 H NMR (400MHz, DMSO) δ8.56(d, J=8.4Hz, 1H), 8.46(d, J=8.3Hz, 1H), 8.22(t, J=8.1Hz, 1H), 8.01(t, J =7.9Hz, 1H), 7.55(s, J=7.4Hz, 1H), 4.20(s, 3H), 3.74(s, 1H), 2.68(s, 3H).

Embodiment 2

[0029] Embodiment two: the synthesis of compound 4

[0030] Weigh 0.25g (1.68mmol) of 2-methyl-benzothiazole into a 25ml round bottom flask, add about 1g of methyl iodide and 5ml of absolute ethanol in 6 times the molar amount, and react at 80°C for 15 hours. The reacted solution was cooled to room temperature, then 5ml of absolute ethanol and chloroform were added, suction filtered after shaking, and the precipitate was washed with a small amount of ethanol and chloroform, and after vacuum drying, Compound 4 was obtained as a white powdery solid 0.448g. The rate is 91.7%: 1 H NMR (400MHz, DMSO) δ8.44(d, J=8.1Hz, 1H), 8.30(d, J=8.4Hz, 1H), 7.90(t, J=7.8Hz, 1H), 7.81(t, J =7.7Hz, 1H), 4.20(s, 3H), 3.54(s, 1H), 3.17(s, 3H).

Embodiment 3

[0031] Embodiment three: the synthesis of compound 5

[0032] Weigh 0.50 g each of compounds 2 and 4, add them into a round bottom flask containing 10 ml of methanol, stir at room temperature for 6 minutes, then add 2 ml of 0.5 mol / L sodium bicarbonate aqueous solution, and stir at room temperature for about 1 hour. Add 4ml of saturated KI solution to the reacted solution, stir for about 15 minutes, then filter with suction, then wash with 10ml of water and 4ml of acetone to finally obtain a brick red solid, and obtain 0.98g of compound 5 after drying, with a yield of 81.7%: 1 H NMR (400MHz, DMSO) δ8.77(d, J=8.3Hz, 1H), 8.18(d, J=8.7Hz, 1H), 8.02-7.96(m, 2H), 7.74(d, J=8.2Hz , 2H), 7.59(t, J=7.7Hz, 1H), 7.39(t, J=7.5Hz, 1H), 7.34(s, 1H), 6.85(s, 1H), 4.07(s, 3H), 3.98 (s,3H), 2.87(s,3H).

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Abstract

The invention discloses a fluorescent probe and a manufacturing method thereof and application of the fluorescent probe in detection on ribose nucleic acid (RNA). The probe has a thiazole orange styrene structure which is shown in a chemical structural formula (I) (please see the formula in the description) and is simple and stable in structure and easy to manufacture. The probe can be used for specific detection on RNA, wherein RNA in a solution can be quickly detected through a fluorespectro photometer or directly through visual inspection under fluorescent lamp irradiation; the probe also can be used for detecting or labeling or displaying existence and distribution of RNA in living cells. The fluorescent material has the efficient and specific recognition capacity on ribose nucleic acid (RNA), has the advantages of very good cell membrane permeability, low photoinduced toxicity, biotoxicity and light bleaching property and the like and overcomes the defects that other detection methods are high in cost and equipment requirement, relatively complex in technical operation and the like.

Description

technical field [0001] The invention relates to a fluorescent probe and its preparation method, as well as its use in detecting RNA in aqueous solution, in gel and in cells and imaging nucleoli in cells. Background technique [0002] Small-molecule probes refer to detectors developed for a specific target biomolecule or biological ion. Small-molecule probes can specifically interact with specific target molecules and can be detected by special detection techniques. Compared with ordinary detection technologies, probe technology has the advantages of high sensitivity, strong specificity, fast and accurate, and is suitable for molecular imaging and real-time monitoring. [0003] RNA (ribonucleic acid) plays an important regulatory role in the whole process of organism growth, development and apoptosis; in the occurrence of many diseases, RNA plays a key role, such as the occurrence of malignant tumors and abnormal expression of RNA close relationship. However, compared with ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D417/06G01N21/64
Inventor 卢宇靖邓强张焜方岩雄胡冬萍王郑亚杜志云黄宝华
Owner GUANGDONG UNIV OF TECH
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