Fluorescent probe taking styrene polyperoxide substitutive pyridine compound as G-quadruplex nucleic acid

A fluorescent probe and quadruplex technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of poor selectivity limiting the application of C61, failure to recognize the secondary structure of G-quadruplex, etc., and achieve a good cell membrane Permeability, good photostability, simple preparation

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

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Problems solved by technology

However, C61 cannot effectively recognize the G-quadruplex secondary structure from other forms of nucleic acid molecules, so the poor selectivity limits the application of C61

Method used

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  • Fluorescent probe taking styrene polyperoxide substitutive pyridine compound as G-quadruplex nucleic acid
  • Fluorescent probe taking styrene polyperoxide substitutive pyridine compound as G-quadruplex nucleic acid
  • Fluorescent probe taking styrene polyperoxide substitutive pyridine compound as G-quadruplex nucleic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment one: the synthesis of compound 3c

[0037] Weigh 1.10 g of 2,6-lutidine, 5.00 g of sulfolane, and 2.50 g of methyl iodide with a balance in a fume hood, place them in a 50 mL round bottom flask and add a stirrer, place in an oil bath at 50°C, and turn on magnetic stirring. There was no obvious change in the reaction system and no reflux. After 4h, the reaction was stopped, and there was a white solid in the round bottom flask. After cooling to room temperature, 15 mL of ethyl acetate was added, and a white solid precipitated out. Continue magnetic stirring for 0.5 h, filter with suction, and wash the filter residue with ethyl acetate. After drying, it was weighed to obtain 2.44 g of 1,2,6-trimethylpyridinium iodide M-DP, with a yield of 95.31%. The product is white solid particles. Then weigh 0.51g of M-DP, 1.00g of indole-3-carboxaldehyde ID, 15mL of n-butanol, and 15 drops of 4-methylpiperidine, and place them in a 50mL round-bottomed flask successively...

Embodiment 2

[0038] Embodiment two: the synthesis of compound 6a

[0039]Weigh 1.10g of 2,4,6-collidine, 5.00g of sulfolane, and 2.20g of methyl iodide in a fume hood, place them in a 50mL round bottom flask and add a stirrer, put them in a 70°C oil bath, turn on the condensed water and Magnetic stirring. After 2h, the reaction stopped, there was a white solid in the round bottom flask, and the solution was pale yellow-green. After cooling to room temperature, 15 mL of ethyl acetate was added to the flask, and a white solid precipitated out. Stir magnetically for 0.5 h, filter with suction, and rinse the filter residue with an appropriate amount of ethyl acetate. The filter residue was dried and weighed to obtain 2.25 g of 1,2,4,6-tetramethylpyridinium iodide M-TP. Yield 85.50%. Then weigh 0.54g of M-TP, 1.66g of 4-methylthiobenzaldehyde, 15mL of n-butanol, and 15 drops of 4-methylpiperidine, and place them in a 50mL round-bottomed flask successively, in an oil bath at 95°C, and turn o...

Embodiment 3

[0040] Embodiment three: the synthesis of compound 6b

[0041] Weigh 1.10g of 2,4,6-collidine, 5.00g of sulfolane, and 2.20g of methyl iodide in a fume hood, place them in a 50mL round bottom flask and add a stirrer, put them in a 70°C oil bath, turn on the condensed water and Magnetic stirring. After 2h, the reaction stopped, there was a white solid in the round bottom flask, and the solution was pale yellow-green. After cooling to room temperature, 15 mL of ethyl acetate was added to the flask, and a white solid precipitated out. Stir magnetically for 0.5 h, filter with suction, and rinse the filter residue with an appropriate amount of ethyl acetate. The filter residue was dried and weighed to obtain 2.25 g of 1,2,4,6-tetramethylpyridinium iodide M-TP. Yield 85.50%. Then weigh 0.54g of M-TP, 1.45g of indole-3-carboxaldehyde, 15mL of n-butanol, and 15 drops of 4-methylpiperidine, and place them in a 50mL round-bottomed flask successively, in an oil bath at 110°C, turn on...

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Abstract

The invention discloses a fluorescent probe and a preparation method thereof and an application of the fluorescent probe in detection of a nucleic-acid G-quadruplex structure. The structure of the probe is as shown in the formula (I), and the probe is simple and stable in structure and easy to prepare. The invention further discloses the fact that the probe can be used in specific detection of a nucleic-acid G-quadruplex secondary structure, and the G-quadruplex secondary structure in a solution can be detected through a fluorospectro photometer; the probe can be used in detection of the nucleic-acid G-quadruplex structure in sepharose gel or polyacrylamide gel; the probe can also be used in detecting, marking or displaying existence and distribution of the G-quadruplex structure in living cells. The fluorescent material has efficient and exclusive recognition capability on the nucleic-acid G-quadruplex structure and has the advantages of good cell membrane permeability, low photoinduced toxicity, biotoxicity and light bleaching property and the like, and shortcomings that other detection methods are high in cost, high in equipment requirement, relative complex in technical operation and the like are overcome.

Description

technical field [0001] The invention relates to a fluorescent probe and its preparation method, as well as its use in detecting the secondary structure of nucleic acid G-quadruplex in aqueous solution, in gel and in cells. Background technique [0002] Nucleic acid is not only the basic component of all biological cells, but also plays a dominant role in the growth, development, reproduction, inheritance and variation of organisms and other major life phenomena. Nucleic acid macromolecules are divided into two categories: deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), which play a role in storing and transmitting genetic information in the replication and synthesis of proteins. [0003] G-quadruplex (G-quadruplex) is a special nucleic acid secondary structure. Many guanine-rich regions in the human genome have the ability to form this structure, including the guanine repeat at the end of the telomeric region, and the promoter regions of various genes, such as c-kit...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64C12Q1/68C07D401/14C07D213/20
Inventor 卢宇靖胡冬萍张焜方岩雄邓强王郑亚杜志云黄宝华
Owner GUANGDONG UNIV OF TECH
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