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Fluorescent probe for detecting sulfur ions in mitochondria and application thereof

A technology of fluorescent probes and sulfide ions, applied in the field of fluorescent probes, can solve problems such as the inability to detect sulfide ions and the lack of mitochondrial positioning functions, and achieve good solubility and biocompatibility, good chemical stability, and good cell communication. The effect of permeability

Active Publication Date: 2014-07-23
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many kinds of fluorescent probes for detecting sulfur ions, but most of them do not have the function of mitochondrial localization, let alone detect the sulfur ions produced in mitochondria

Method used

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  • Fluorescent probe for detecting sulfur ions in mitochondria and application thereof
  • Fluorescent probe for detecting sulfur ions in mitochondria and application thereof
  • Fluorescent probe for detecting sulfur ions in mitochondria and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1R

[0023] Embodiment 1RhS-1 fluorescent probe

[0024]

[0025] 300mmol rhodamine 123 and 900mmol phosphorus oxychloride POCl 3 Add it to 120 mL of dry 1,2-dichloroethane, heat to reflux for 4 hours, and remove the solvent under reduced pressure. Add 50 mL of dry acetone and 300 mmol of sodium azide aqueous solution (mass concentration: 5%), and react at 0° C. for 24 hours. The reaction solution was extracted with dichloromethane, the lower layer was removed, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography (200-300 mesh) to obtain a bright black product RhS-1 with a yield of 33%, MS: 355.1022.

Embodiment 2

[0026] Embodiment 2RhS-2 fluorescent probe

[0027]

[0028] Mix 300mmol of rhodamine 6G with 900mmol of phosphorus oxychloride POCl 3 Add it to 120 mL of dry 1,2-dichloroethane, heat to reflux for 4 hours, and remove the solvent under reduced pressure. Add 50 mL of dry acetone and 300 mmol of sodium azide aqueous solution (mass concentration: 5%), and react at 0° C. for 24 hours. The reaction solution was extracted with dichloromethane, the lower layer was removed, dried over anhydrous magnesium sulfate, separated and purified by silica gel (200-300 mesh) column chromatography to obtain bright black RhS-2 with a yield of 34%, MS: 439.1789.

Embodiment 3

[0029] Embodiment 3RhS-3 fluorescent probe

[0030]

[0031] 300mmol of tetramethylrhodamine and 900mmol of phosphorus oxychloride POCl 3 Add it to 120 mL of dry 1,2-dichloroethane, heat to reflux for 4 hours, and remove the solvent under reduced pressure. Add 50 mL of dry acetone and 300 mmol of sodium azide aqueous solution (mass concentration: 5%), and react at 0° C. for 24 hours. The reaction solution was extracted with dichloromethane, the lower layer was removed, dried over anhydrous magnesium sulfate, separated and purified by silica gel (200-300 mesh) column chromatography to obtain bright black RhS-3 with a yield of 51%, MS: 412.1543.

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Abstract

The invention relates to a fluorescent probe for detecting sulfur ions in mitochondria. The fluorescent probe is an RhS fluorescent probe, and the structural general formula of the RhS fluorescent probe is shown in the formula (I). The fluorescent probe can be rapidly positioned in the mitochondria and used for performing online real-time detection on the sulfur ions and hydrogen sulfide ions in the mitochondria. In addition, the probe also has relatively good chemical and optical stability, relatively good solubility and bio-compatibility and relatively high sulfur ion selectivity without interferences caused by other species such as reactive oxygen, reactive nitrogen and the like. Laser confocal imaging experiments show that the probe has relatively good cell permeability without causing toxic or side effects to cells and organisms.

Description

technical field [0001] The invention relates to a kind of fluorescent probe which can be positioned at the mitochondria of living cells and detect sulfur ions in the mitochondria. Background technique [0002] Hydrogen sulfide plays an important role in life sciences and is the third most important gas messenger molecule after nitric oxide and carbon monoxide. Since the discovery in the 1990s that endogenous hydrogen sulfide (HS) exerts physiological and pathological effects in the body, people have started a new understanding and exploration of HS. Studies in recent years have shown that the body has the generation of endogenous HS, which has similar effects to nitric oxide (NO): it can relax blood vessels and smooth muscles of the digestive tract, inhibit the proliferation of vascular smooth muscle cells, etc., and has a role in the nervous system. Participate in important regulatory roles. In addition, HS is a gas molecule with a relatively small molecular mass, which c...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/82C07D491/147C07D491/22G01N21/64
Inventor 宋有涛于海波王宁王杰琼李红玲曹珍
Owner LIAONING UNIVERSITY
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