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A visible-light excitable ratiometric fluorescent temperature-sensitive probe based on europium complex and its preparation method and application

A europium complex, ratiometric fluorescence technology, applied in thermometers with physical/chemical changes, fluorescence/phosphorescence, indium organic compounds, etc., can solve the problems of low temperature resolution and high cytotoxicity, and achieve sensitive and good temperature response. Biocompatible, good reversible effect

Active Publication Date: 2019-02-26
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the probes for intracellular temperature detection are mainly single-emitting organic dyes as fluorescent chromophores, but the detection probes have disadvantages such as low temperature resolution and high cytotoxicity.

Method used

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  • A visible-light excitable ratiometric fluorescent temperature-sensitive probe based on europium complex and its preparation method and application
  • A visible-light excitable ratiometric fluorescent temperature-sensitive probe based on europium complex and its preparation method and application
  • A visible-light excitable ratiometric fluorescent temperature-sensitive probe based on europium complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Probe Synthesis

[0041] Step 1, preparation of europium complex

[0042] Compound 1: Preparation of 5-nitro-1,10-phenanthroline

[0043] Add 5.0g of 1,10-phenanthroline into a round bottom flask, add 45.0mL of concentrated sulfuric acid to dissolve it, then add 25.0mL of concentrated nitric acid dropwise, reflux at 165°C for 2h, cool to room temperature, and dissolve the reaction solution dropwise Drop into ice water. Adjust the solution to slightly acidic with 10% sodium hydroxide solution. The precipitated yellow precipitate was the product, which was filtered with suction, washed with water and dried in vacuo. Yield 5.1 g (82%) of a pale yellow solid. GC-MS (EI-m / z): 225 (M + ).

[0044]

[0045] Compound 2: Preparation of 5-amino-1,10-phenanthroline

[0046] Add 5.0g of 5-nitro-1,10-phenanthroline and 0.9g of Pd / C into a round bottom flask, blow nitrogen to remove oxygen, add 150.0mL of absolute ethanol to dissolve it, and then add N 2 h 4 ·H ...

Embodiment 2

[0071] Embodiment 2 P1 emission spectrum test

[0072] Configure the dilute solution of P1 obtained in Example 1, use water as the solvent, pipette 2.0mL of the solution into a fluorescence cuvette, and then use different excitation wavelengths for testing at 37°C, such as figure 2 As shown, the wavelengths are 405nm, 413nm, 418nm, 428nm, 438nm, 448nm, 458nm, 468nm, 478nm, 488nm. The test data shows that the iridium complex as an "antenna molecule" can extend the excitation window of europium to the visible light range of 468nm.

[0073] Emission spectrum test at different temperatures: such as image 3 As shown, the excitation wavelength is 405nm, and the test temperature range is 20-42°C, respectively 20°C, 22°C, 24°C, 26°C, 28°C, 30°C, 32°C, 34°C, 36°C, 38°C, 40°C ℃, 42 ℃, the test data show that as the temperature increases, the emission intensity of iridium gradually increases, and the emission intensity of europium does not change much.

[0074] Such as Figure 4 As ...

Embodiment 3

[0076] Example 3 Confocal imaging experiments of polymer probes detecting temperature in living cells

[0077] The cells used in this example are human cervical cancer HeLa cells, at 37°C, 5% CO 2 Continue to culture for 24 hours under the same conditions to make it adhere to the wall, add polymer probes (5μM), incubate for one hour and perform confocal experiments, and use the live cell workstation to control the temperature. Such as Image 6 As shown, the emission intensity of iridium has obvious changes at different temperatures, indicating that the probe can detect the temperature of living cells very well.

[0078] The ratiometric fluorescent temperature-sensitive probe based on the iridium complex sensitized europium complex of the present invention can realize double emission, and the ratio of the two fluorescence peaks has a linear relationship with the temperature change, such as image 3 shown. The probe has the ability to detect temperature and can realize visual...

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Abstract

The invention discloses a visible light excitable ratio fluorescence thermosensitive probe based on a europium complex and a preparation method and application of the probe. The structural general formula of the probe is as shown below. Compared with the prior art, the probe has the advantages that according to the probe, the emission intensity ratio of iridium and europium is obviously changed along with temperature change, and responses to temperature are very sensitive; the probe has good reversibility; the probe has good stability and water solubility; the probe has good biocompatibility, can be used for temperature detection of aqueous solutions or cells or living bodies, and plays an important role in the fields of biological temperature detection, biological imaging and biological labeling. Please see the formula in the description.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and relates to a temperature-sensitive probe, in particular to a visible-light-excitable ratiometric fluorescent temperature-sensitive probe based on europium complexes, and a preparation method and application thereof. Background technique [0002] In recent years, with the continuous development of life sciences, the research on the temperature change in cells has become more and more in-depth. Intracellular temperature is closely related to every biological reaction in the cell, such as enzyme reaction, gene expression, cell division, metabolism, etc. Every biological reaction is endothermic or exothermic, therefore, cells in different parts are different due to different biological reactions. In pathological research, it is found that some malignant cells and tissues have higher temperature than healthy cells and tissues due to abnormal metabolic rate. Therefore, accurate dete...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K9/02G01N21/64G01K11/20
CPCC07F15/0033C09K9/02G01K11/20G01N21/6428
Inventor 赵强黄维张华杰刘淑娟许文娟蒋嘉洋
Owner NANJING UNIV OF POSTS & TELECOMM
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