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Mitochondrial targeting superoxide anion imaging probe and preparation method thereof

A technology of mitochondria and carbon number, applied in the field of mitochondria-targeted superoxide anion imaging probe and its preparation, which can solve the problem of reactive oxygen species hazards and the like

Active Publication Date: 2016-10-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In conclusion, in the general cellular environment, reactive oxygen species are essential for living organisms, but excessive reactive oxygen species can cause harm

Method used

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  • Mitochondrial targeting superoxide anion imaging probe and preparation method thereof
  • Mitochondrial targeting superoxide anion imaging probe and preparation method thereof
  • Mitochondrial targeting superoxide anion imaging probe and preparation method thereof

Examples

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Embodiment 1

[0063] Example 1. Preparation and application of mitochondria-targeted superoxide anion imaging probe Mito-Superoxide-tracker

[0064] (1) Preparation of mitochondria-targeted superoxide radical probe Mito-Superoxide-tracker

[0065] as per figure 1 The synthetic route shown prepares the mitochondria-targeted superoxide radical imaging probe Mito-Superoxide-tracker.

[0066] (1) Dissolve 4-nitrofluorescein in THF solvent, slowly add diphenylphosphoryl chloride dropwise to the reaction solution at 20°C, and control the molar ratio of 4-nitrofluorescein to diphenylphosphoryl chloride at 1 : 2.1, stirred and reacted at 80°C for 10h, cooled to 20°C at the end of the reaction, evaporated the reaction solvent, separated and purified through column and recrystallization to obtain intermediate product I.

[0067] The results of structural confirmation are as follows: 1 H NMR (300MHz, DMSO, TMS): δ8.65(s, 2H), 8.41(m, J=7.5Hz, 1H), 7.86-7.78(m, J=7.5Hz, 8H), 7.65-7.60(d ,J=7.5Hz,1H...

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Abstract

The invention discloses a mitochondrial targeting superoxide anion imaging probe and a preparation method thereof. The mitochondrial targeting superoxide anion imaging probe has a structural formula shown in the formula I or I'. A series of the mitochondrial targeting superoxide anion imaging probes are designed and synthesized. A mitochondrial targeting group is introduced to a benzene ring of benzovalerolactone of the probe, can directionally target cell mitochondria and has high selectivity to cell mitochondria. Through esterification of two hydroxyl groups of 4-nitrofluorescein and diphenylphosphinyl chloride, a probe chain with double detection groups is introduced and can selectively detect superoxide radical. The probe realizes real-time and high-selectivity detection of superoxide anion production in mitochondria, does not react with other reactive oxygen in mitochondria and has specificity to superoxide anion detection.

Description

technical field [0001] The invention relates to a mitochondria-targeted superoxide anion imaging probe and a preparation method thereof, belonging to the fields of molecular detection and molecular imaging. Background technique [0002] Mitochondria are two-membrane organelles that are ubiquitous in most eukaryotic cells, with diameters ranging from 0.5 to 10 microns. Mitochondria are the main sites for oxidative phosphorylation and synthesis of adenosine triphosphate (ATP) in cells, which provide energy for cell activities, so they are called "cell power factories". In addition to supplying energy for cells, mitochondria are also involved in such things as regulating membrane potential and controlling programmed cell death; regulation of cell differentiation, cell proliferation and cell metabolism; synthesis of cholesterol and some heme; responsible for cell information transmission and have the ability to regulate cell growth and Cell Cycle Competence. [0003] Free radi...

Claims

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Application Information

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IPC IPC(8): C07F9/6561C09K11/06G01N21/64
Inventor 黄赛朋杜立波刘扬
Owner INST OF CHEM CHINESE ACAD OF SCI
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