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Singlet oxygen fluorescence probe based on europium complex and its application

A technique of fluorescent probes and europium complexes, which is applied in the field of singlet oxygen measurement in living cells, can solve the problems of poor water solubility of probes, unfavorable measurement, and inability to use real-time measurement, and achieves high stability and enhanced fluorescence intensity. Effect

Inactive Publication Date: 2007-06-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has good selectivity, high sensitivity, and rapid detection, but the poor water solubility of the probe is not conducive to biological systems. 1 o 2 Determination of
[0005] Although the various measurement methods mentioned above have been 1 o 2 However, these methods cannot be used in living cells due to the severe interference of various components in the cell with optical measurement methods. 1 o 2 real-time determination of

Method used

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  • Singlet oxygen fluorescence probe based on europium complex and its application
  • Singlet oxygen fluorescence probe based on europium complex and its application
  • Singlet oxygen fluorescence probe based on europium complex and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1. Ligand [4'-(10-methyl-9-anthracenyl)-2,2': 6'2”-bitripyridine-6,6”-dimethylamine]tetraacetic acid (abbreviation MTTA) synthesis.

[0031] The synthetic route is shown in Figure 1, and the matrix operation process is as follows.

[0032] (1) Synthesis of (E)-3-(10-methyl-9-anthryl)-1-(2'-pyridyl)-2-propenone (Compound 1)

[0033] After 11.01 g of 10-methyl-9-anthracene (50 mmol) and 2.81 g of KOH (50 mmol) are mixed and dissolved in a mixed solution composed of 150 ml of methanol and 30 ml of water, 6.06 g of 2-acetylpyridine (50 mmol) is slowly added dropwise In the reaction system, stir at room temperature for 24 hours. The precipitate was collected by filtration, washed thoroughly with ethanol and dried in vacuum to obtain 13.19 g of the target compound, yield: 81.6%. 1 HNMR(CDCl 3 ) Measurement results: δ = 3.15 (s, 3H); 7.48-7.57 (m, 5H); 7.92 (m, 1H); 8.23 ​​(d, 1H); 8.30 (d, 1H); 8.34 to 8.40 (m, 4H) ); 8.69(d, 1H); 8.94(d, 1H).

[0034] (2) Synthesis of 4'...

Embodiment 2

[0049] Example 2. Probe MTTA-Eu 3+ And with 1 O 2 Combined with the internal oxide EP-MTTA-Eu 3+ Determination of the fluorescence properties of

[0050] (1) Fluorescence spectrum, fluorescence intensity and fluorescence lifetime

[0051] MTTA-Eu was measured using 0.05mol / L sodium borate buffer solution with pH 9.1 as the solvent 3+ The ultraviolet-visible spectrum, fluorescence spectrum, molar extinction coefficient (ε), fluorescence quantum yield (φ) and fluorescence lifetime (τ) in the solvent. EP-MTTA-Eu 3+ By MTTA-Eu 3+ With Na 2 MoO 4 / H 2 O 2 0.1mol / L NaHCO at pH 10.5 3 -Prepared in NaOH buffer solution (the product is verified by mass spectrometry), and then diluted 100 times with a 0.05mol / L sodium borate buffer solution with pH 9.1, and then determine its fluorescence properties in the solvent. The instrument for measuring the ultraviolet-visible spectrum is a Perkin Elmer Lambda35 spectrophotometer. The fluorescence measuring instrument is a Perkin Elmer LS 50B fluores...

Embodiment 3

[0059] Example 3. Using MTTA-Eu 3+ Quantitative determination of Na 2 MoO 4 / H 2 O 2 Produced by the system 1 O 2

[0060] 0.1mol / L NaHCO at pH 10.5 3 -Add MTTA-Eu to NaOH buffer solution separately 3+ (1.0μmol / L), Na 2 MoO 4 (1.0mmol / L) and a series of concentrations of H 2 O 2 (Every 2 molecules of H in the system 2 O 2 Produces 1 molecule 1 O 2 ). After the reaction was placed at 37°C, the reaction solution was subjected to time-resolved fluorescence spectrometry. The measuring instrument is a Perkin Elmer LS 50B fluorescence spectrophotometer.

[0061] As shown in Figure 5, with H 2 O 2 Concentration (i.e. 1 O 2 Concentration) increases, the fluorescence intensity of the probe also gradually increases, indicating that MTTA-Eu 3+ Can be used to quantitatively determine the 1 O 2 concentration. Figure 6 shows the use of MTTA-Eu 3+ Detection of Na 2 MoO 4 / H 2 O 2 Quantitatively produced in the system 1 O 2 Working curve. as the picture shows, 1 O 2The concentration and fluoresc...

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Abstract

The present invention relates to new europium complex fluorescent probe for the imaging determination of singlet oxygen in live cell and its application. The fluorescent probe is complex formed with trivalent europium ion Eu3+ and organic ligand [4'-(10-methyl-9-anthryl)-2, 2':6'2''-tripyridyl-6, 6''-dimethyl amino] tetracetic acid as shown. The complex can enter to live cell simply in the presence of photosensitizer and capture singlet oxygen in cell specifically, leading to obviously enhanced fluorescence strength of the complex for the fluorescent determination of singlet oxygen in live cell.

Description

Technical field [0001] The invention relates to a technique for measuring singlet oxygen in living cells, in particular to a europium complex fluorescent probe that can be used for imaging and measuring singlet oxygen in living cells and its application. Background technique [0002] Singlet oxygen ( 1 O 2 ) Is an unstable form of oxygen molecules in a high-energy excited state. It is widespread in nature and plays a very important role in many photochemical and photobiological reaction processes, such as photodegradation, phototransformation of pollutants, chemiluminescence, oxidative aging of organisms, and even photocarcinogenesis. There have been many reports on the application of singlet oxygen in organic synthesis, but its physiological oxidation in biological systems has attracted more and more attention from researchers. It contains a significant impact on biology and life systems. Biomolecules, including membrane lipids, proteins, amino acids, nucleotides, carbohydrates ...

Claims

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Application Information

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IPC IPC(8): C07F5/00G01N21/64
Inventor 袁景利宋波王桂兰谭明乾
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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