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A kind of ribosomal rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative and its preparation method and application

A two-photon fluorescence and terpyridine technology, which is applied in the field of ribosomal rRNA fluorescent probes, can solve the problems that the molecular structure of SYTO probes is not disclosed, cannot specifically recognize rRNA, and limits the research of SYTO probes, so as to achieve good results in tumors and kidneys. Tissue penetration, low cost, and good photostability

Active Publication Date: 2020-01-31
ANHUI UNIVERSITY
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  • Abstract
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Problems solved by technology

However, many molecules have poor permeability to the nuclear membrane and are difficult to enter the nucleus, so there are not many reports on rRNA probes
Currently, the only RNA probes available on the market are the SYTO series of RNA probes. Since the molecular structure of the SYTO probes has not been disclosed, further research on the SYTO probes has been greatly limited.
[0005] In 2006, Qian Li and Young-Tae Chang of New York University used three pyridinium salts to recognize RNA in living cells. In the same year, David Parker's research group at Durham University used Eu complexes to specifically recognize nucleoli, but the above RNA probes are single-photon fluorescent probes
The probes mentioned above all recognize RNA in the nucleolus and cytoplasm of the cell at the same time, and cannot specifically recognize rRNA, mRNA or tRNA

Method used

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  • A kind of ribosomal rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative and its preparation method and application
  • A kind of ribosomal rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative and its preparation method and application
  • A kind of ribosomal rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative and its preparation method and application

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Embodiment Construction

[0050] The ribosomal rRNA two-photon fluorescent probe (J1) of the present invention is a quaternary ammonium salt terpyridine derivative, and the structural formula is as follows:

[0051]

[0052] The synthesis method of ribosomal rRNA two-photon fluorescent probe of the present invention comprises the following steps:

[0053] Step 1: Synthesis of Intermediate B1

[0054] Weigh 2g (4.85mmol) N,N-dihydroxyethylaniline terpyridine (Q1) into a 150mL round-bottom flask, add a mixed solvent of 80mL acetonitrile and 20mL N,N-dimethylformamide (DMF), pass through Enter N 2 , slowly add 1.97g (7.2mmol) of phosphorus tribromide dropwise under ice bath conditions, then gradually heat up to 80°C, and heat under reflux for 8h; after the reaction is completed, cool to room temperature, pour into ice water to adjust pH to neutral, pump Filter, wash with water and dry to obtain a light yellow solid; the obtained light yellow solid is washed with water, extracted and dried successivel...

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Abstract

The invention discloses a ribosome rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative as well as a preparation method and application thereof. The structural formula of the ribosome rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative is as shown in the description. A target product disclosed by the invention can identify RNA by two-photon fluorescent enhancement and realizes a two-photon fluorescent enhancement identification effect; and low-energy long wave (710 nm) excitation has little damage to a living body. The rRNA in cell nucleolus is specifically identified. The colocalization effect of the target product disclosed by the invention and nucleolus Syto9 at the cell nucleolus is good, and a Pearson coefficient can reach 90 percent.

Description

[0001] 1. Technical field [0002] The invention relates to a ribosome rRNA fluorescent probe, in particular to a ribosome rRNA two-photon fluorescent probe-quaternary ammonium salt terpyridine derivative and its preparation method and application. [0003] 2. Background technology [0004] Recently, German biochemist Thomas Carell proposed in the journal Science that RNA is the first self-replicating molecule that forms all life and can be used as the origin of life. RNA molecules include transfer RNA (tRNA), messenger RNA (mRNA) and ribosomal RNA (rRNA), which have many functions, such as transport in vivo, interpretation of genetic information, regulation of gene expression, and some necessary biocatalysis. Among them, rRNA is the most abundant RNA in the cell, and it can combine with protein in the nucleolus to produce ribosomes. With the help of rRNA fluorescent probes, the presence and activity of rRNA in vivo can be observed under a confocal microscope. However, many m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/38C09K11/06C12Q1/68G01N21/64
CPCC07B2200/13C07D213/38C09K11/06C09K2211/1029C12Q1/68G01N21/6402
Inventor 吴杰颖杜威李兴宇祝英忠田肖和王慧张琼周虹屏田玉鹏
Owner ANHUI UNIVERSITY
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