Fluorescent probe and preparation method thereof

A fluorescent probe, -et technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as cumbersome operating procedures, troublesome probe purification, and difficult removal of fluorescent dyes

Pending Publication Date: 2020-07-17
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods, without exception, can only be used as probes by introducing fluorescent molecules into the probes in advance, and the operating procedures are cumbersome during use, the residual fluorescent dyes in the system are difficult to remove, and the purification of the probes is difficult. is also very troublesome

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  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof

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preparation example Construction

[0103] An embodiment of the present invention also provides a method for preparing a fluorescent probe, comprising the following steps:

[0104] 1) Put nitroso or hydroxyamino substituted aromatic compounds and 1,3-diene compounds in a mixed solvent of acetonitrile and water in a molar ratio of 1:1 to 10 (volume ratio, acetonitrile: water = 1:1 to 6), react at 0-60°C for 15 minutes to 4 hours;

[0105] 2) The mixed solvent of acetonitrile and water was removed in vacuo, and then separated by column chromatography (H60 silica gel column, ethyl acetate:n-hexane=1:1-10) to obtain fluorescent probe molecules.

[0106] The obtained fluorescent probe molecules are the aforementioned first fluorescent probe molecules or second fluorescent probe molecules.

[0107] In step 1), the molecular structural formula of the nitroso-substituted aromatic compound is:

[0108]

[0109] R 3 -H (hydrogen), -Me (methyl), -Et (ethyl), -Pr (propyl), -iPr (isopropyl), -Bu (butyl), -tBu (tert-but...

Embodiment 1

[0141] Fluorescent probe molecule Probe 1 (referred to as P 1, [English full name: Benzyl3-(2-methyl-1,3-dioxoisoindolin-5-yl)-2-oxa-3-azaspiro[bicyclo[2.2.1]hept[5 ]ene-7,4'-piperidine]-1'-carboxylate]) is as follows:

[0142]

[0143] The synthetic method of fluorescent probe molecule P1:

[0144] Dissolve 53.8mg (0.2mmol) benzyl 8-azaspiro[4.5]deca-1,3-diene-8-carboxylate and 41.8mg (0.22mmol) 2-methyl-5-nitrosoisoindoline-1,3-dione in acetonitrile / water (2.0 ~ 4.0mL). Stir at 25°C. Then the reaction solvent was concentrated and purified by column chromatography to obtain the corresponding fluorescent probe molecule P1 (H60 silica gel column, ethyl acetate:n-hexane=1:2).

[0145] NMR spectroscopy analysis:

[0146] 1 H NMR (400MHz, CDCl 3 )δ7.61-7.63(d,J=8Hz,1H),7.32-7.37(m,6H),7.11-7.14(dd,J=4Hz,8Hz,1H),6.32-6.35(m,1H),5.94 -5.97(m,1H),5.140(s,2H),4.81-4.83(m,1H),4.73-4.75(m,1H),3.56-3.58(m,2H),3.40-3.44(m,2H) ,3.12(s,3H),1.86-1.98(m,2H),1.58-1.60(m,2H); 13 C N...

Embodiment 2

[0150] Fluorescent probe molecules are referred to as P1 structural formula as follows:

[0151]

[0152] The synthetic method of fluorescent probe molecule P1:

[0153]Dissolve 53.8mg (0.2mmol) benzyl 8-azaspiro[4.5]deca-1,3-diene-8-carboxylate and 42.2mg (0.22mmol) 5-(hydroxyamino)-2-methylisoindoline-1,3-dione in acetonitrile / water (2.0-4.0mL). Stir at 25°C. Then the reaction solvent was concentrated and purified by column chromatography to obtain the corresponding fluorescent probe molecule P1 (H60 silica gel column, ethyl acetate:n-hexane=1:2).

[0154] NMR spectroscopy analysis:

[0155] 1 H NMR (400MHz, CDCl 3 )δ7.61-7.63(d,J=8Hz,1H),7.32-7.37(m,6H),7.11-7.14(dd,J=4Hz,8Hz,1H),6.32-6.35(m,1H),5.94 -5.97(m,1H),5.140(s,2H),4.81-4.83(m,1H),4.73-4.75(m,1H),3.56-3.58(m,2H),3.40-3.44(m,2H) ,3.12(s,3H),1.86-1.98(m,2H),1.58-1.60(m,2H); 13 C NMR (100MHz, CDCl 3 )δ168.55, 168.34, 156.37, 136.73, 133.67, 132.52, 131.71, 128.53, 128.07, 124.21, 123.96, 110.85, 99.98, 85...

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Abstract

The invention discloses a fluorescent probe and a preparation method thereof, and the preparation method comprises the following steps: placing a nitroso or hydroxylamino substituted aromatic compoundand a 1, 3-diene compound in a solvent, and reacting for 15 minutes to 4 hours; and removing the solvent in vacuum, and separating in a column chromatography mode to obtain the fluorescent probe molecule. The fluorescent probe provided by the invention is a fluorescent probe capable of carrying out in-situ specific recognition, and compared with the existing fluorescent probe, the fluorescent probe provided by the invention has the advantages of low cost of raw materials required by molecular synthesis, simple preparation process, stable fluorescence luminescence property and high signal-to-noise ratio.

Description

technical field [0001] The invention relates to a biochemical detection tool and a preparation method thereof, in particular to a novel fluorescent probe molecule and a synthesis method thereof. Background technique [0002] Specific biomolecular imaging is one of the powerful tools in biomedical research, which can provide biologists with a wonderful starting point to visually infer the underlying biological mechanisms in various and complex biological processes. To this end, researchers have done a lot of work to discover and expand this toolbox of biological imaging. Protein labeling currently mainly uses methods such as fluorescent proteins (such as GFP, namely green fluorescent protein), self-labeling proteins (such as SNAP tags), ligases (such as lipoic acid ligase) and self-labeling tags (such as tetracysteine) . Although these methods can achieve rapid labeling, they need to modify the target protein. These modifications may interfere with the normal structure and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D413/04C07D498/10C09K11/06
CPCC07D413/14C07D413/04C07D498/10C09K11/06C09K2211/1033
Inventor 蒋先兴
Owner SUN YAT SEN UNIV
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