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Rare earth dysprosium cryptand fluorescent complex and preparation method thereof

A technology of complexes and dysprosium cryptand, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of high price, few practical applications, and low yield, so as to improve sensitivity and accuracy, Good application prospect, simple process effect

Inactive Publication Date: 2021-02-09
济南国科医工科技发展有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, although a variety of cryptate complexes have been reported at home and abroad, there are not many practical applications. An ideal cryptate complex must have a high molar absorption coefficient, high luminous efficiency, long fluorescence lifetime, and good water solubility. Chemical stability and excited state (not easy to be quenched by foreign gas, water, etc.), but also easy to label biomolecules
There are very few rare earth fluorescent complexes of cryptane that have been commercialized, such as Eu 3+ ,Tb 3+ The cryptane complex is already available for sale, but the price is very expensive, the price is above 10,000 / mg, and this complex has many steps to synthesize, and the yield is extremely low; moreover, the solubility of the compound is not ideal, which will complicate the labeling process change
For example, the rare earth cryptane fluorescent complex shown in the following formula (Ⅲ) has a molar extinction coefficient of 20000M -1 cm -1 When used to detect indicators, the detection limit can only reach 10 -9 g / L, unable to meet the requirements of some testing indicators

Method used

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  • Rare earth dysprosium cryptand fluorescent complex and preparation method thereof
  • Rare earth dysprosium cryptand fluorescent complex and preparation method thereof
  • Rare earth dysprosium cryptand fluorescent complex and preparation method thereof

Examples

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Effect test

Embodiment 1

[0051] The present embodiment provides a rare earth dysprosium cryptane fluorescent complex, which has a chemical structural formula shown in the following formula (I):

[0052]

[0053] Among them, the chemical structural formula of the complex MO is shown in the following formula (II):

[0054]

Embodiment 2

[0056] This example provides a method for preparing the rare earth dysprosium cryptane fluorescent complex as described in Example 1. The synthetic route of the rare earth dysprosium cryptand fluorescent complex is as follows:

[0057]

[0058] Wherein, the synthetic route of described complex MO is:

[0059]

[0060] The preparation method of the rare earth dysprosium cryptane fluorescent complex comprises the following steps:

[0061] 1. Synthesis of complex MO:

[0062] Concrete preparation method comprises the following steps:

[0063] 1) The compound (9.27mmol) shown in formula (II-1) and p-toluenesulfonamide sodium (18.5mmol) were refluxed for 24 hours in dry ethyl acetate (350ml), and cooled to- After 5°C to -10°C, filter the mixture and wash with ethyl acetate to obtain a white insoluble solid, which is the compound shown in formula (II-2); its H-NMR detection result is as follows: figure 1 As shown, its structural confirmation data is: 1 H-NMR (400MHz, CDCl ...

Embodiment 3

[0073] Embodiment 3 Fluorescence spectrum detection of rare earth dysprosium cryptane fluorescent complex

[0074] The detection method is: in a 10.0mL volumetric flask, add the dimethylsulfoxide stock solution (10 μg / mL, 1mL) of the rare earth dysprosium cryptane fluorescent complex synthesized in Example 2, tris-hydrochloric acid (Tris- HCl) buffer solution (1X10 -3 mol / L, 1mL) and double distilled water (3mL), diluted to the mark with dimethyl sulfoxide solution, shaken up, left at room temperature for 10min, and moved into a 1cm quartz cuvette (Cary Eclipse fluorescence spectrophotometer, American VARIAN company ) for fluorescence spectrometry.

[0075] Test results such as Figure 6-7 as shown, Figure 6 is the absorption spectrum of the rare earth dysprosium cryptane fluorescent complex, Figure 7It is the emission spectrum of the rare earth dysprosium cryptane fluorescent complex. It can be seen that the fluorescence emission signal is stable and can form a fluores...

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Abstract

The invention discloses a rare earth dysprosium cryptand fluorescent complex and a preparation method thereof. The complex has a chemical structural formula as shown in a formula (I) in the description, wherein the chemical structural formula of the complex MO is as shown in a formula (II) in the description. The molar extinction coefficient of the rare earth dysprosium cryptand fluorescent complex provided by the invention can be increased by about 4 times (80000M<-1>cm<-1>) compared with that of the existing product, the rare earth dysprosium cryptand fluorescent complex is suitable for being used as a fluorescent dye molecule to mark nucleic acid, protein and other biomolecules, and the detection sensitivity and accuracy can be improved; and the preparation method disclosed by the invention is relatively simple in process and high in product yield, and has a very good application prospect.

Description

technical field [0001] The invention relates to the technical field of preparation of coordination compounds, in particular to a rare earth dysprosium cryptane fluorescent complex and a preparation method thereof. Background technique [0002] As a new immunoassay technology, time-resolved fluorescence resonance energy transfer has the advantages of high sensitivity, strong specificity, and high accuracy, and is gradually favored by researchers at home and abroad. Time-resolved fluorescence resonance energy transfer technology (Homogeneous Time-Resolved Fluorescence) is a technology that combines two methods: fluorescence resonance energy transfer (FRET, Fluorescence Resonance Energy Transfer) and time-resolved fluorescence (TRF, Time-Resolved Fluorescence). The technique utilizes the energy transfer of two fluorophores known as (energy) donors and (energy) acceptors. The donor is excited by an external energy source (e.g. receptors in sufficient [0003] Within a short di...

Claims

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Application Information

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IPC IPC(8): C07D471/22C09K11/06G01N21/64
CPCC07D471/22C09K11/06C09K2211/182G01N21/6428G01N2021/6417
Inventor 刘元忠孙靖刘坤良于海利
Owner 济南国科医工科技发展有限公司
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