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Fluorescence probe based on BODIPY type singlet oxygen

A fluorescent probe, singlet oxygen technology, applied in the field of fluorescent probes, to achieve the effects of high fluorescence quantum yield, low cytotoxicity, and high molar extinction coefficient

Inactive Publication Date: 2017-08-18
HUNAN CITY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, among these probes, fluorescent probes for singlet oxygen using BODIPY dyes as a design platform have rarely been reported.

Method used

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  • Fluorescence probe based on BODIPY type singlet oxygen
  • Fluorescence probe based on BODIPY type singlet oxygen
  • Fluorescence probe based on BODIPY type singlet oxygen

Examples

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Embodiment Construction

[0027] The following examples are only used to illustrate the present invention in detail and do not limit the scope of the invention in any way.

[0028] The synthesis of embodiment probe:

[0029] Accurately weigh 9,10-2-methyl-2-aldoanthracene (1.17 g, 5.0 mmol) dissolved in dry CH 2 Cl 2 (500 mL), under a nitrogen atmosphere, slowly drop into freshly distilled 2,4-dimethylpyrrole (1.1 mL, 12.5 mmol), and then add 0.1 mL of trifluoroacetic acid as a catalyst, the reaction solution gradually changed from clear to Turn into blood red, and react for 10 hours under stirring at room temperature. Then dichlorodicyanobenzoquinone (DDQ) (1.13 g, 5.0 mmol) dissolved in dry tetrahydrofuran was injected with a syringe, and the reaction was continued for 0.5 h under stirring at room temperature. Under the condition of ice-water bath, slowly add triethylamine (10.0 mL, 71.9 mmol), continue to stir for 15 min after the addition, then slowly add boron trifluoride diethyl ether (10.0 mL...

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Abstract

The invention discloses a fluorescence probe based on BODIPY type singlet oxygen. The fluorescence probe has the characteristics of high sensitivity, high selectivity and fast response in a neutral environment for detection of singlet oxygen. The fluorescence probe has no fluorescence, fluorescence is obviously enhanced after response with the singlet oxygen, the fluorescence intensity and the concentration of the singlet oxygen have good linear relation, the fluorescence probe can be used for quantitative detection, and other active oxygen substances do not interfere detection. The prepared fluorescence probe has classic BODIPY spectral characteristic, can detect mercury ions in chemical samples, biological samples or medical samples on the basis of fluorescence enhancement or chromaticity enhancement, and is suitable for fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of fluorescent probes and specifically designs a preparation method and application of an enhanced singlet oxygen fluorescent probe based on BODIPY fluorescent dye. Background technique [0002] In biological systems, singlet oxygen ( 1 o 2 ) is an important reactive oxygen species. 1 o 2 With high chemical activity and large diffusion radius, it can penetrate the mitochondrial membrane or nuclear membrane and cause DNA damage; it can interact with histones, and histidine residues pass through 1 o 2 Oxidation produces a new photoproduct. Moreover, its amount is directly proportional to cell damage and death; it can oxidize cysteine, histidine, tryptophan, methionine and tyrosine residues, making proteins lose their function; it can make enzyme protein molecules undergo intramolecular Or intermolecular cross-linking, leading to configuration changes and inactivation or exposing some hidden peptide bonds and being...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1029C09K2211/1055G01N21/643G01N21/6486G01N2021/6432
Inventor 龙立平王姣亮谢丹
Owner HUNAN CITY UNIV
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