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Europium complex singlet oxygen fluorescent probe with cell membrane permeability and its application

A technology of singlet oxygen and europium complexes, which is applied in the field of fluorescent probes and its applications, can solve the problems of difficult and widespread use in cancer PDT research, and achieve the enhancement of fluorescence quantum yield and fluorescence lifetime, good water solubility and stability , the effect of high sensitivity

Inactive Publication Date: 2012-10-17
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the probe cannot enter the cell through the cell membrane when it is co-cultured with cells, it is difficult to widely use it in cancer PDT research.

Method used

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  • Europium complex singlet oxygen fluorescent probe with cell membrane permeability and its application
  • Europium complex singlet oxygen fluorescent probe with cell membrane permeability and its application
  • Europium complex singlet oxygen fluorescent probe with cell membrane permeability and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of the probe complex [MTDTA-Eu] and its reaction with singlet oxygen

[0032] Synthetic route such as figure 1 As shown, the substrate operation process is as follows.

[0033] (1) Synthesis of compound 3

[0034]First, compound 1 and compound 2 were synthesized by the method of document 10 and document 11 (document 11: C.Galaup, J.M.Couchet, S. Bedel, P.Tisnès, C.Picard, J.Org.Chem.2005,70, 2274). Add 300mg of compound 1 (0.49mmol), 218mg of compound 2 (0.49mmol) and 519mg of potassium carbonate (4.9mmol) into a mixed solvent of 120mL of dry acetonitrile and 100mL of dry tetrahydrofuran (THF), and reflux for 24 hours under stirring. Insoluble matter was removed by filtration, and the solvent was distilled off under reduced pressure. The product was first separated on a silica gel column with 40:8:5 (v / v / v) ethyl acetate-triethylammonia-methanol as the eluent, and then 25:1 (v / v) chloroform-methanol The eluent was separated with an alumina colu...

Embodiment 2

[0041] Example 2: Determination of fluorescence properties of the probe [MTDTA-Eu] and its reaction product [EP-MTDTA-Eu] with singlet oxygen

[0042] (1) Spectral and fluorescent properties

[0043] Using 0.05 mol / L sodium borate buffer solution with a pH value of 9.1 as the solvent, the UV-visible spectra, fluorescence spectra, molar extinction coefficients (ε), and Fluorescence quantum yield (φ) and fluorescence lifetime (τ), the results are shown in Table 1.

[0044] Table 1. MTTA-Eu 3+ and EP-MTTA-Eu 3+ Absorption and fluorescence properties in sodium borate buffer solution

[0045]

[0046] It can be seen from the results in Table 1 that after the probe [MTDTA-Eu] reacted with singlet oxygen to generate [EP-MTDTA-Eu], the fluorescence quantum yield increased from 0.88% to 13.4%, and the fluorescence lifetime increased from 0.31ms to 0.96ms. were significantly enhanced. It shows that the probe [MTDTA-Eu] has a significant fluorescence signal response to singlet ox...

Embodiment 3

[0051] Example 3: Quantitative determination of Na using the probe [MTDTA-Eu] 2 MoO 4 -H 2 o 2 singlet oxygen

[0052] [MTDTA-Eu] (10 μmol / L), Na 2 MoO 4 (1.0mmol / L) and a series of concentrations of H 2 o 2 , and left to react at room temperature for 4 hours, the time-resolved fluorescence spectra of each reaction solution were measured, and the obtained results were as follows: Figure 5 shown. It can be seen that with H 2 o 2 The fluorescence intensity of the probe also gradually increased with the increase of concentration (that is, singlet oxygen concentration), indicating that [MTDTA-Eu] can be used to quantitatively determine singlet oxygen generated in solution. Using a 96 microwell plate on a Perkin-Elmer Victor 1420 time-resolved fluorometer to detect Na using [MTDTA-Eu] 2 MoO 4 -H 2 o 2 The minimum detection limit of singlet oxygen produced in the system was determined, and the minimum detection limit of singlet oxygen determined by this method was 1.3...

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Abstract

The invention relates to a europium complex singlet oxygen fluorescent probe with cell membrane permeability and its application. The probe has a structure as the following. The probe can directly enter a cell through a cell co-culture method, and can be used for time-resolved fluorescence assay of intracellular singlet oxygen and other biochemical determination. The probe can also be used for fluorescence determination or time-resolved fluorescence determination of singlet oxygen in various chemical, photochemical and biochemical systems.

Description

technical field [0001] The invention relates to a fluorescent probe for measuring singlet oxygen and its application, in particular to a europium complex fluorescent probe with cell membrane permeability and its application. Background technique [0002] Singlet oxygen is an unstable oxygen molecule in a high-energy excited state. In the past two decades, cancer photodynamic therapy (PDT) based on the strong oxidative properties of singlet oxygen to kill tumor cells has been More and more applications have been obtained in clinical medicine. This technology usually uses photosensitizers such as porphyrin derivatives such as hematoporphyrin and hematoporphyrin monomethyl ether as therapeutic drugs (document 1: W.M.Sharman, C.M.Allen, J.E.Lier , Drug.Discov.Today.1999,4,507; Literature 2: T.J.Dougherty, J.Clin.Laser.Med.Surg.2002,20,3; Literature 3: X.Ding, Q.Xu, F.Liu, P. Zhou, Y.Gu, J.Zeng, J.An, W.Dai, X.Li, Cancer Lett.2004, 216, 43), when the photosensitizer is enriched ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D471/22C12Q1/02G01N21/64
Inventor 袁景利戴志超叶志强
Owner DALIAN UNIV OF TECH
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