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Fluorescent probe for marking DNA and synthetic method and using thereof

A DNA labeling and fluorescent probe technology, applied in the fields of chemical synthesis and biological analysis, can solve the problems of increased fluorescence quantum yield and low fluorescence quantum yield, and achieve the effect of strong color rendering, low fluorescence background, and large increase multiple

Active Publication Date: 2015-08-19
TIANJIN CHENGJIAN UNIV
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  • Description
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Problems solved by technology

It is the current research trend to study the low fluorescence quantum yield of some dyes in aqueous solution and the significant increase of fluorescence quantum yield after binding with nucleic acid

Method used

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  • Fluorescent probe for marking DNA and synthetic method and using thereof
  • Fluorescent probe for marking DNA and synthetic method and using thereof
  • Fluorescent probe for marking DNA and synthetic method and using thereof

Examples

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preparation example Construction

[0017] A kind of preparation method of fluorescent probe for DNA labeling comprises the following steps:

[0018] Using ethanol as a solvent, add N-(4-butanesulfonic acid)-4-methylquinoline inner salt and 3-formyl-6-(4-vinylpyridine)- 9-ethylcarbazole and a catalytic amount of piperidine are heated and refluxed for 4-8 hours; after the reaction is completed, the solvent is distilled off under reduced pressure, and the fluorescent probe is obtained by silica gel column chromatography.

[0019] Probes interact with DNA.

[0020] The probe was prepared in DMSO to a concentration of 1 × 10 -3 mol / L mother liquor. G-quadruplex DNA was dissolved in Tri-HCl with pH=7.4 and containing 10mmol / L KCl (or NaCl), and its concentration was calculated according to the absorbance value of the sample at 260nm and the molar extinction coefficient.

[0021] UV absorption spectrometry. The total volume of the sample to be tested was prepared to be 500 μL, and the concentration of the compound...

Embodiment 1

[0023] Add N-(4-butanesulfonic acid group)-4-methylquinoline inner salt (0.29g, 1.05mmol), 3-formyl-6-(4-vinylpyridine)- 9-Ethylcarbazole (0.33g, 1.0mmol), 25ml absolute ethanol and 50μL piperidine, heated to reflux for 4 hours after addition, TLC monitored the completion of the reaction, concentrated and separated by column chromatography, and dichloromethane / methanol (10:1) was used as the mobile phase to obtain 0.44 g of fluorescent probe with a yield of 75.0%.

Embodiment 2

[0025] Add N-(4-butanesulfonic acid group)-4-methylquinoline inner salt (0.56g, 2.0mmol), 3-formyl-6-(4-vinylpyridine)- 9-Ethylcarbazole (0.33g, 1.0mmol), 30ml absolute ethanol and 50μL piperidine, heated to reflux for 8 hours after addition, TLC monitored the completion of the reaction, concentrated and separated by column chromatography, and dichloromethane / methanol (3:1) was used as the mobile phase to obtain 0.38 g of the fluorescent probe with a yield of 66.1%.

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Abstract

The invention discloses a fluorescent probe for marking DNA and synthetic method and using thereof. The method and step include that ethanol is used as solvent, N - (4 - butyl sulfonic group) - 4 - methyl quinoline in salt and 3 - formyl - 6 - (4 - vinyl pyridine) - 9 - ethyl carbazole with the mole ratio of 1.05 to 2:1 are added, and piperidine of catalytic amount is also added, and then the solvent is heated reflux for 4 to 8 hours. After reaction, the solvent is removed by vacuum distillation. The fluorescent probe is got after chromatography by silicagel column. The fluorescent probe for marking DNA and the double-stranded DNA (ds26) have strong function each other, and have potential application values in synthetic anticancer drugs. The fluorescent probe for marking DNA has the advantages of low fluorescence background, high combination property with double-stranded DNA (ds26), simple preparation method and high structural stability.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and biological analysis, in particular to a method for preparing a fluorescent probe for DNA labeling. Background technique [0002] DNA is the main genetic material in living organisms. Nucleic acid chains in organisms include single-stranded, double-stranded, triple-helix, and quadruplex structures. These structures are interconnected and transformed, and play an important role in the growth, development, and reproduction of organisms. Therefore, the quantitative analysis and specific recognition of DNA molecules are of great significance to the development of virology, molecular biology and other related disciplines. Compared with the traditional isotope detection method, the fluorescent probe method is faster, more reproducible, less dosage, and no radiation. It has been widely used in automatic DNA sequencing, antibody immunoassay and anticancer drug analysis. At the same time, DNA molecu...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/14C12Q1/68
Inventor 谷迎春费学宁林大勇李冉
Owner TIANJIN CHENGJIAN UNIV
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