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Fluorescent probe Mito-HNO, preparation method thereof and application of fluorescent probe Mito-HNO in detection of HNO in mitochondria

A fluorescent probe and reaction technology, applied in chemical instruments and methods, luminescent materials, pharmaceutical formulations, etc., can solve problems such as short time, difficult capture, and limitations, achieve deep tissue penetration depth, facilitate in vivo imaging, and design strategies and the effect of the simplicity of the synthetic route

Inactive Publication Date: 2020-12-08
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, since HNO is a substance that can react spontaneously, it is extremely difficult to capture in vivo for a short time, so the method and means of direct detection of HNO still need to be further developed, which also limits the ability of HNO in many physiological and pathological processes in living cells and in vivo environments. Conducting research on effects

Method used

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  • Fluorescent probe Mito-HNO, preparation method thereof and application of fluorescent probe Mito-HNO in detection of HNO in mitochondria
  • Fluorescent probe Mito-HNO, preparation method thereof and application of fluorescent probe Mito-HNO in detection of HNO in mitochondria
  • Fluorescent probe Mito-HNO, preparation method thereof and application of fluorescent probe Mito-HNO in detection of HNO in mitochondria

Examples

Experimental program
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Effect test

Embodiment 1

[0046]Synthesis of fluorescent probes

[0047] The synthesis of hydroxy merocyanine (substance 4) was synthesized according to the existing reports. Dissolve the raw material 2-diphenylphosphobenzoic acid (5mmol), dicyclohexylcarbodiimide (5mmol), and 4-dimethylaminopyridine (0.25mmol) in 15mL of dichloromethane, activate the carboxyl group at 0°C for 30min, Hydroxy merocyanine (1 mmol) was then added and stirred at room temperature for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Then using dichloromethane:methanol=20:1 as eluent, purified by column chromatography to obtain Mito-HNO (57%) as a blue-purple solid.

[0048] NMR and mass spectrometry characterization:

[0049] 1 H NMR (400MHz, CDCl 3 )δ=8.71(d,J=15.2Hz,1H),8.36–8.31(m,1H),8.20(d,J=8.4Hz,1H),8.05(dd,J=18.2,8.5Hz,2H), 7.73–7.66(m,2H),7.62–7.52(m,3H),7.39–7.24(m,12H),7.11(d,J=1.8Hz,1H),7.07–7.05(m,1H),6.83– 6.76(m,2H),4.86(q,J=7.3Hz,2H),2.82(dt,J=63.9,5.7Hz,4H),2.07(s,...

Embodiment 2

[0061] Synthesis of fluorescent probes

[0062] The synthesis of hydroxy merocyanine (substance 4) was synthesized according to the existing reports. Dissolve the raw materials 2-diphenylphosphobenzoic acid (1mmol), dicyclohexylcarbodiimide (1mmol), and 4-dimethylaminopyridine (0.05mmol) in 15mL of dichloromethane, activate the carboxyl group at 0°C for 30min, Hydroxy merocyanine (1 mmol) was then added and stirred at room temperature for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Then using dichloromethane:methanol=20:1 as eluent, purified by column chromatography to obtain Mito-HNO (15%) in blue-purple solid.

Embodiment 3

[0064] Synthesis of fluorescent probes

[0065] The synthesis of hydroxy merocyanine (substance 4) was synthesized according to the existing reports. Dissolve the raw material 2-diphenylphosphobenzoic acid (3mmol), dicyclohexylcarbodiimide (3mmol), and 4-dimethylaminopyridine (0.15mmol) in 15mL of dichloromethane, activate the carboxyl group at 0°C for 30min, Hydroxy merocyanine (1 mmol) was then added and stirred at room temperature for 12 h. After the reaction was complete, the solvent was removed by rotary evaporation. Then using dichloromethane:methanol=20:1 as eluent, purified by column chromatography to obtain Mito-HNO (24%) as blue-purple solid.

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Abstract

The invention relates to the technical field of mitochondria targeted positioning detection, in particular to a fluorescent probe MitoHNO, a preparation method thereof and application of the fluorescent probe Mito-HNO in detection of HNO in mitochondria. The structural formula of the fluorescent probe Mito-HNO is shown in the specification, the fluorescent probe has a specific mitochondria targeting positioning effect, emitted light is located in a near-infrared region, and the fluorescent probe Mito-HNO has the advantages of being large in tissue penetration depth, beneficial to living body imaging and the like, can be successfully applied to an animal model and is a novel imaging tool; the biocompatibility is good, and the damage to cells and living bodies is small; the probe has photoacoustic performance and can also be developed into a photoacoustic probe; the design strategy and the synthetic route are simple and convenient, and the raw materials are cheap and easily available.

Description

technical field [0001] The invention relates to the technical field of mitochondrial targeting detection detection, in particular to a fluorescent probe Mito-HNO and a preparation method thereof and its application in detecting HNO in mitochondria. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Mitochondria, widely present in most cells, is a subcellular organelle structure for cells to produce energy, and is the main place for aerobic respiration. Plays a role in many important cellular processes by providing energy through the oxidative respiratory chain. Examples include ATP production, intermediary metabolism, calcium regulation and redox signaling, and cell apoptos...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C09K11/06A61K49/00
CPCC07F9/65586C09K11/06A61K49/0021C09K2211/1029C09K2211/1088C09K2211/1014C09K2211/1007
Inventor 唐波王慧李平聂君伟王洪统
Owner SHANDONG NORMAL UNIV
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