High water-solubility ruthenium metal complex singlet oxygen fluorescent probe, preparation method thereof, and application thereof

A technology of ruthenium complexes and singlet oxygen, applied in fluorescence/phosphorescence, compounds containing elements of group 8/9/10/18 of the periodic table, luminescent materials, etc., to achieve good selectivity, high detection sensitivity, and water solubility Good results

Inactive Publication Date: 2012-02-08
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these complexes can detect singlet oxygen under visible light excitation, the complexes show large background fluorescence in the absence of singlet oxygen, and the water solubility, detection sensitivity and selectivity of singlet oxygen still need to be further improved.

Method used

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  • High water-solubility ruthenium metal complex singlet oxygen fluorescent probe, preparation method thereof, and application thereof
  • High water-solubility ruthenium metal complex singlet oxygen fluorescent probe, preparation method thereof, and application thereof
  • High water-solubility ruthenium metal complex singlet oxygen fluorescent probe, preparation method thereof, and application thereof

Examples

Experimental program
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Embodiment 1

[0050] Embodiment 1, ligand aip-C 4 h 8 -SO 3 Na and the complex [Ru(aip-C 4 h 8 -SO 3 Na) 3 ] Cl 2 Synthesis.

[0051] The synthetic route is as follows:

[0052]

[0053] The basic operation process is as follows:

[0054] 1. Ligand aip-C 4 h 8 -SO 3 Synthesis of Na.

[0055] aip was synthesized according to the literature [M.Mariappan, B.G.Maiya, Effects of anthracene and pyrene units on the interactions of novel polypyridylruthenium(II) mixed-ligand complexes with DNA. Eur. J. Inorg. Chem. 2005, 2164.].

[0056] Under the protection of nitrogen, weigh NaH (0.19g, 7.88mmol, 50% dispersed in mineral oil), wash with redistilled n-hexane three times, add 20mL redistilled DMF, aip (1.2g, 3.03mmol), and heat under reflux for three Hour. After cooling to room temperature, 1,4-butanesulfonyllactone (557mg, 4.24mmol) was added, stirred at room temperature for one hour, then slowly raised to 110°C, and refluxed for 24 hours, during which orange precipitates precipit...

Embodiment 2

[0063] Embodiment 2, the method and detection performance of complex probe singlet oxygen in buffer solution

[0064] 1. With [Ru(aip-C 4 h 8 SO 3 Na) 3 ] Cl 2 As an example, the method and detection performance of the complex of the present invention as a fluorescent probe for detecting singlet oxygen in neutral and alkaline solutions are introduced.

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Abstract

The invention discloses a high water-solubility ruthenium metal complex singlet oxygen fluorescent probe, a preparation method thereof, and an application thereof. According to the invention, a transition metal ruthenium is adopted as a central ion of the ruthenium complex; and anthracene nucleus derivatives with sodium (or potassium) sulfonate groups are adopted as ligands. The ruthenium complex has properties of a singlet oxygen fluorescent probe and a better water-solubility than existing anthracene nucleus derivative ligand ruthenium complexes. The ruthenium complex is suitable for quantitative or qualitative determinations of <1>O2 in neutral or basic system solutions.

Description

technical field [0001] The present invention relates to singlet oxygen ( 1 o 2 ), specifically relates to the preparation and application of a ruthenium metal complex singlet oxygen fluorescent probe containing an anthracycline derivative ligand. Background technique [0002] Singlet oxygen is an unstable form of oxygen molecules in a high-energy excited state. Its chemical properties are very active, and it is more unstable than ground state oxygen. It is one of the so-called active oxygen species. The content of active oxygen species in normal human cells is very small, and they are in a balanced state in a healthy human body, and these active oxygen species produced in the body play an important role in life activities. They participate in a variety of physiological activities in the body, such as signaling conduction, nerve transmission, regulation of muscle tension, peristalsis, aggregation of platelets and regulation of blood pressure, control of the immune system, l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D471/16C09K11/06G01N21/64G01N33/52
Inventor 王克志尹红菊李奇刘艳菊
Owner BEIJING NORMAL UNIVERSITY
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