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 res

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

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027] Example 1: Synthesis of Compound 2

[0028] Weigh 0.2 g (1.1236 mmol) of 4-chloro-quinaldine into a 25 ml round-bottomed flask, add about 0.96 g of methyl iodide and 1.5 ml of sulfolane in a 6-fold molar amount, and heat the mixture to 50° C. After 18 hours of reaction , cooled, shaken after adding anhydrous ether, suction filtered, the solid was washed with anhydrous ether, vacuum-dried and weighed to obtain 0.345g of compound 2 with a yield of 95.8%: 1 H NMR (400MHz, DMSO) δ 8.56 (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).

Example Embodiment

[0029] Example 2: Synthesis of Compound 4

[0030] Weigh 0.25 g (1.68 mmol) of 2-methyl-benzothiazole into a 25 ml round-bottomed flask, add about 1 g of methyl iodide and 5 ml of absolute ethanol in a 6-fold molar amount, and react at 80°C for 15 hours. The reacted solution was cooled to room temperature, then 5 ml of absolute ethanol and chloroform were added, and after shaking, suction filtration was performed, and a small amount of ethanol and chloroform was used to wash the precipitate. After vacuum drying, compound 4 was obtained as a white powdery solid 0.448 g. The rate is 91.7%: 1 H NMR (400MHz, DMSO) δ 8.44 (d, J=8.1 Hz, 1H), 8.30 (d, J=8.4 Hz, 1H), 7.90 (t, J=7.8 Hz, 1H), 7.81 (t, J =7.7Hz, 1H), 4.20 (s, 3H), 3.54 (s, 1H), 3.17 (s, 3H).

Example Embodiment

[0031] Example 3: Synthesis of Compound 5

[0032] Weigh 0.50 g each of compounds 2 and 4 into a round-bottomed flask containing 10 ml of methanol, stir at room temperature for 6 minutes, add 2 ml of 0.5 mol / L sodium bicarbonate aqueous solution, and stir at room temperature for about 1 hour. 4ml of saturated KI solution was added to the reacted solution, stirred for about 15 minutes, filtered with suction, washed with 10ml of water, and washed with 4ml of acetone to finally obtain a brick-red solid. After drying, 0.98g of compound 5 was obtained with a yield of 81.7%: 1 H NMR (400MHz, DMSO) δ 8.77 (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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