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Fluorescent probe for selectively detecting RNA G-quadruplex in cells as well as preparation method and application of fluorescent probe

A technology of fluorescent probes and quadruplexes, applied in the field of fluorescent probes, to achieve the effects of increasing fluorescence intensity, enhancing push-pull electronic effects, and improving optical properties

Active Publication Date: 2018-06-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, fluorescent probes that can specifically recognize RNAG-quadruplexes in vivo or in vitro have rarely been reported.

Method used

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  • Fluorescent probe for selectively detecting RNA G-quadruplex in cells as well as preparation method and application of fluorescent probe
  • Fluorescent probe for selectively detecting RNA G-quadruplex in cells as well as preparation method and application of fluorescent probe
  • Fluorescent probe for selectively detecting RNA G-quadruplex in cells as well as preparation method and application of fluorescent probe

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Embodiment 1

[0032] The synthesis of embodiment 1 compound f1~f7

[0033] ① Mix 10g 3,4-difluoroaniline and 10g ethyl acetoacetate into a round bottom flask, add 120g polyphosphoric acid (PPA), react at 130°C for 5 hours, cool to room temperature, pour the reaction solution into 500mL ice In water, the solution was adjusted to neutrality with saturated sodium hydroxide, filtered under reduced pressure, and dried to obtain 12.40 g of a light yellow solid, that is, compound (a).

[0034] ②Dissolve 10g of compound (a) in 50mL of phosphorus oxychloride, reflux at 110°C for 5h, cool to room temperature, pour into 500mL of ice water, adjust the solution to be weakly alkaline with saturated sodium hydroxide solution, and filter under reduced pressure. Dry crude product. Purification by silica gel chromatography using petroleum ether / dichloromethane (volume ratio 2 / 1) as the eluent gave 8.30 g of a white solid, namely compound (b).

[0035] ③Dissolve 8g of compound (b) in 100mL of methanol, add ...

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Abstract

The invention provides a fluorescent probe for selectively detecting an RNA G-quadruplex in cells as well as a preparation method and application of the fluorescent probe. The fluorescent probe has astructure represented by a formula (I) shown in the description, wherein Ar is an aromatic ring or an aromatic heterocyclic ring; R1 is fluorine, amino or an amine substituent; and A<-> is a N methylated anion, an iodide ion, a p-toluenesulfonic acid ion or a trifluoromethanesulfonic acid ion. The fluorescent probe provided by the invention can specifically detect and recognize the RNA G-quadruplex in the cells, the detection process is not interfered by other components, and the real-time tracking of the movement process and folding and unfolding process of the RNA G-quadruplex in living cells is realized; and the fluorescent probe has a simple preparation process, low costs and a stable structure, is convenient for storage, and has broad application space in the biological function research of the RNA G-quadruplex.

Description

technical field [0001] The present invention relates to a fluorescent probe, more specifically to a fluorescent probe for selectively detecting intracellular RNA G-quadruplex and its preparation method and application. Background technique [0002] G-quadruplex (G-quadruplex) is an important nucleic acid secondary structure formed by guanine-rich DNA or RNA. Bioinformatics analysis found that there are about 370,000 sequences in the human genome that have the possibility of forming G-quadruplexes, including the telomere terminal guanine repeat sequence promoter region, ribosomal DNA (rDNA), transcription initiation site (TSS), untranslated region (UTR) and other regions, indicating that the G-quadruplex plays an important role in the human genome and transcriptome, and participates in the regulation of many important life processes. In the past ten years, the research on G-quadruplex mainly focused on DNA G-quadruplex; the research on RNA G-quadruplex was relatively less. ...

Claims

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Application Information

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IPC IPC(8): C07D215/12C07D401/06C07D215/14C07D405/06C09K11/06G01N21/64
CPCC07D215/12C07D215/14C07D401/06C07D405/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1088G01N21/6486
Inventor 谭嘉恒黄志纾陈修财陈硕斌
Owner SUN YAT SEN UNIV
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