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Fluorescent probe for accurately detecting copper ions in mitochondria by light control as well as preparation method and application of fluorescent probe

A fluorescent probe, mitochondrial technology, applied in the field of organic fluorescent probes, can solve the problems of unavoidable interference and lack of convincing research results, and achieve the effects of no toxic side effects, good cell permeability, and good mitochondrial targeting.

Inactive Publication Date: 2017-05-17
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the study of mitochondria, fluorescent probes are mostly used. An ideal fluorescent probe is the dream of countless scientists. So far, many fluorescent probes have been reported, such as the detection of active oxygen clusters, active nitrogen clusters, metal ions, biological Fluorescent probes such as small molecules, but these fluorescent probes have a fatal shortcoming that they cannot avoid interference from the detected substances in the cytoplasm during the process of targeting mitochondria through the cytoplasm, resulting in a lack of convincing research results

Method used

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  • Fluorescent probe for accurately detecting copper ions in mitochondria by light control as well as preparation method and application of fluorescent probe
  • Fluorescent probe for accurately detecting copper ions in mitochondria by light control as well as preparation method and application of fluorescent probe
  • Fluorescent probe for accurately detecting copper ions in mitochondria by light control as well as preparation method and application of fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0027] The preparation method of the fluorescent probe for accurately measuring copper ions in mitochondria by light regulation is as follows:

[0028] (1) Preparation of fluorescein hydrazide: Dissolve 1 g of fluorescein in 50 mL of methanol, add dropwise 4 mL of hydrazine hydrate, reflux for 10 hours, remove the solvent, and purify by silica gel column chromatography to obtain fluorescein hydrazide;

[0029] (2) Preparation of photoprotective fluorescein hydrazide: dissolve 108mg fluorescein hydrazide and 82mg 2-nitrobenzyl bromide in 3mL DMF, add 405mg cesium carbonate at room temperature for 6 hours, wash and extract with water, and purify by silica gel column chromatography to obtain Photoprotective fluorescein hydrazide;

[0030] (3) Preparation of photoprotected fluorescein derivatives: Dissolve 253 mg of photoprotected fluorescein hydrazide and 131.7 mg of 1,4-dibromobutane into 4 mL of DMF, add 664.4 mg of cesium carbonate and catalytic amount of potassium iodide to r...

Embodiment 2

[0034]The preparation method of the fluorescent probe for accurately measuring copper ions in mitochondria by light regulation is as follows:

[0035] (1) Preparation of fluorescein hydrazide: Dissolve 0.8 g of fluorescein in 50 mL of methanol, dropwise add 3.7 mL of hydrazine hydrate, reflux for 12 hours, remove the solvent, and purify by silica gel column chromatography to obtain fluorescein hydrazide;

[0036] (2) Preparation of photoprotective fluorescein hydrazide: dissolve 158 mg fluorescein hydrazide and 125 mg 2-nitrobenzyl bromide in 4 mL of DMF, add 593.6 mg cesium carbonate at room temperature for 10 hours, wash and extract with water, and purify by silica gel column chromatography Obtain photoprotected fluorescein hydrazide;

[0037] (3) Preparation of photoprotected fluorescein derivatives: dissolve 100 mg of photoprotected fluorescein hydrazide and 57 mg of 1,4-dibromobutane in 2 mL of DMF, add 267 mg of cesium carbonate and a catalytic amount of potassium iodide...

Embodiment 3

[0040] The preparation method of the fluorescent probe for accurately measuring copper ions in mitochondria by light regulation is as follows:

[0041] (1) Preparation of fluorescein hydrazide: Dissolve 1 g of fluorescein in 50 mL of methanol, add dropwise 4.5 mL of hydrazine hydrate, reflux for 14 hours, remove the solvent, and purify by silica gel column chromatography to obtain fluorescein hydrazide;

[0042] (2) Preparation of photoprotective fluorescein hydrazide: Dissolve 200mg fluorescein hydrazide and 185.3mg 2-nitrobenzyl bromide in 4mL DMF, add 751.4mg cesium carbonate at room temperature for 12 hours, wash and extract with water, pass through a silica gel column layer analysis and purification to obtain photoprotected fluorescein hydrazide;

[0043] (3) Preparation of photoprotected fluorescein derivatives: dissolve 123 mg of photoprotected fluorescein hydrazide and 76 mg of 1,4-dibromobutane in 3 mL of DMF, add 323 mg of cesium carbonate and a catalytic amount of p...

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Abstract

The invention relates to a fluorescent probe for accurately detecting copper ions in mitochondria by light control as well as a preparation method and application of the fluorescent probe, and belongs to the field of organic fluorescent probes. The fluorescent probe is a Mito-Cu<2+> fluorescent probe; a structural formula of the Mito-Cu<2+> fluorescent probe is shown as a formula (I). The fluorescent probe disclosed by the invention can be used for accurately detecting the copper ions in the mitochondria and avoiding the interference of the copper ions in cells. Besides, the probe has the characteristics of better mitochondrial targeting ability, chemical stability, biological compatibility, selectivity and the like. A laser confocal imaging experiment shows that the probe has better cell permeability and has no toxic or side effects on the cells and living organisms. (The formula is shown in the description).

Description

technical field [0001] The invention relates to a fluorescent probe for accurately detecting copper ions in mitochondria through light regulation, a preparation method and application thereof, and belongs to the field of organic fluorescent probes. Background technique [0002] In the mitochondria, copper ions are an important trace element and an integral part of a series of important physiological enzymes, such as transport and catalytic enzymes. When the copper ion imbalance in the mitochondria will destroy the mitochondrial respiratory chain, a series of signs of apoptosis will appear, such as the increase of the content of reactive oxygen species, the decrease of mitochondrial membrane potential, lipid peroxidation, and the release of cytochrome c. The interaction of copper ions and proteins is also seen as a signal for neurodegenerative diseases such as Parkinson's and Alzheimer's diseases. Cu in mitochondria 2+ The precise detection of copper ions will help us furth...

Claims

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Application Information

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IPC IPC(8): C07F9/6561C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07F9/65615C09K2211/1029C09K2211/1088
Inventor 李林黄维王刘林陈步祥张承武刘金华胡明宇赵燕菲彭平平
Owner NANJING UNIV OF TECH
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