A kind of cell membrane targeted mg2+ fluorescent probe and its preparation method and application

A technology of fluorescent probes and cell membranes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as difficulty in judging concentration changes, and achieve the effect of enhanced fluorescence intensity and dynamic reversible response

Inactive Publication Date: 2018-06-26
SUZHOU INSTITUE OF WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to intracellular Mg 2+ The concentration change is Mg 2+ The combined result of the two processes of uptake / exit into the cell, both abnormal uptake and excretion can cause intracellular Mg 2+ Changes, difficult to judge intracellular Mg 2+ The exact cause of the change in concentration

Method used

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  • A kind of cell membrane targeted mg2+ fluorescent probe and its preparation method and application
  • A kind of cell membrane targeted mg2+ fluorescent probe and its preparation method and application
  • A kind of cell membrane targeted mg2+ fluorescent probe and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 2.10 g of trimellitic anhydride (0.1 mol) in 50 mL of dichloromethane, add dropwise a solution of 2.4 g of hexadecylamine (0.1 mol) in 50 mL of dichloromethane at room temperature, stir the mixture at room temperature for 1 hour, and remove the solvent under reduced pressure. 4.1 g of crude hexadecyl trimellitic anhydride was obtained, which was directly used in the next reaction without further purification.

[0031] Add 416 mg hexadecyl trimellitic anhydride (1 mmol) and 154 mg 2,4-dihydroxybenzoic acid (1 mmol) to 20 mL methanesulfonic acid, and keep warm at 85° C. for 3 hours. Cool to room temperature, neutralize methanesulfonic acid with 5mol / L NaOH solution, and then acidify with 1mol / L hydrochloric acid, a large amount of orange-yellow precipitates are formed. The solid was collected by filtration, separated and purified by column chromatography to obtain 65 mg of 1-carboxy-5-formylhexadecanylfluorescein. 1 H NMR: 0.87-0.90(t,3H),1.28(s,28H),3.40-3.46(m...

Embodiment 2

[0033] Dissolve 2.10 g of trimellitic anhydride (0.1 mol) in 50 mL of dichloromethane, add dropwise a solution of 2.4 g of hexadecylamine (0.1 mol) in 50 mL of dichloromethane at room temperature, stir the mixture at room temperature for 3 hours, and remove the solvent under reduced pressure. The crude product of hexadecyl trimellitic anhydride was directly used in the next reaction without further purification.

[0034] Hexadecyl trimellitic anhydride (1 mmol) and 154 mg of 2,4-dihydroxybenzoic acid (1 mmol) were added to 20 mL of methanesulfonic acid, and kept at 40° C. for 24 hours. Cool to room temperature, neutralize methanesulfonic acid with 5mol / L NaOH solution, and then acidify with 1mol / L hydrochloric acid, a large amount of orange-yellow precipitates are formed. The solid was collected by filtration, separated and purified by column chromatography to obtain 1-carboxy-5-formylhexadecanylfluorescein.

Embodiment 3

[0036] Dissolve 2.10 g of trimellitic anhydride (0.1 mol) in 50 mL of dichloromethane, add dropwise a solution of 2.4 g of hexadecylamine (0.1 mol) in 50 mL of dichloromethane at room temperature, stir the mixture at room temperature for 5 hours, and remove the solvent under reduced pressure. The crude product of hexadecyl trimellitic anhydride was directly used in the next reaction without further purification.

[0037] Hexadecyl trimellitic anhydride (1 mmol) and 154 mg of 2,4-dihydroxybenzoic acid (1 mmol) were added to 20 mL of methanesulfonic acid, and kept at 90° C. for 1 hour. Cool to room temperature, neutralize methanesulfonic acid with 5mol / L NaOH solution, and then acidify with 1mol / L hydrochloric acid, a large amount of orange-yellow precipitates are formed. The solid was collected by filtration, separated and purified by column chromatography to obtain 1-carboxy-5-formylhexadecanylfluorescein.

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Abstract

The invention discloses a cell membrane-targeted fluorescent probe for Mg2+ detection, a preparation method and application thereof. The carboxyl group on the probe and its adjacent carbonyl group have the ability to complex Mg2+. The carboxyl group and the phenolic hydroxyl group dissociate under neutral to slightly alkaline conditions to form a water-soluble group. The target label is on the outer surface of the cell membrane and cannot Pass through the cell membrane and enter the cell; in addition, the probe itself has weak fluorescence, and can selectively combine with Mg2+ under physiological conditions to generate a derivative product with strong fluorescence. When the Mg2+ in the area where the probe is located decreases, it binds The dissociation of Mg2+ can dynamically monitor the process of intracellular Mg2+ discharge to the outside. The preparation method of the cell membrane targeting Mg2+ fluorescent probe provided by the invention only needs two steps, and is simple and easy.

Description

technical field [0001] The invention relates to a method capable of dynamically monitoring Mg in cells through fluorescence imaging 2+ A cell membrane-targeted fluorescent probe released extracellularly and a preparation method and application thereof belong to the technical field of biological detection. Background technique [0002] Mg 2+ It is the most widespread divalent metal ion in cells, and plays a decisive role in many physiological processes such as cell proliferation and apoptosis, DNA synthesis control, protein phosphorylation, and energy transfer. Therefore, cells and even tissues Medium Mg 2+ The concentration and distribution of ions are the basic issues of related scientific research in the fields of biology and medicine. [0003] Mg 2+ Physiological effects are closely related to its concentration, however Mg 2+ It is a simple ion, composed of only one atom, with a stable valence state, difficult to generate and destroy, and can only maintain and change...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06C09K2211/1088G01N21/6428
Inventor 郭小峰王红
Owner SUZHOU INSTITUE OF WUHAN UNIV
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