Luminescence quenchers and fluorogenic probes for detection of reactive species

A compound and aromatic amine technology, applied in the field of manufacturing the aromatic amine compound, can solve problems such as changing protein structure, dimerization, protein fragmentation, etc.

Active Publication Date: 2011-03-02
VERSITECH LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, hypochlorite may alter protein structure

Method used

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  • Luminescence quenchers and fluorogenic probes for detection of reactive species
  • Luminescence quenchers and fluorogenic probes for detection of reactive species
  • Luminescence quenchers and fluorogenic probes for detection of reactive species

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0368] The synthetic scheme of embodiment 1-compound 1-4

[0369] Synthesis of compound 8

[0370]

[0371] To a solution of resorufin (2.13 g, 10 mmol) in 50 mL of anhydrous dimethylformamide was added sodium hydride (437 mg, 11 mmol, 60% dispersion in mineral oil) at 0°C. After stirring at 0°C for half an hour, N-phenylbis-trifluoromethanesulfonamide (4.3 g, 12 mmol) was added to the solution. The resulting mixture was stirred at room temperature overnight, then quenched with water. Then 1N hydrochloric acid was added to the mixture to acidify the solution to pH 2. Then ethyl acetate was added. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography to give compound 8.

[0372] Synthetic compound 1

[0373]

[0374] Palladium(II) acetate (2 mg, 1% mmol), 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl (BINAP) (9 mg, 1.5% mmol) and cesium carbonate...

Embodiment 2

[0380] The synthetic scheme of embodiment 2-compound 5-7

[0381] Synthesis of compound 9

[0382]

[0383] To a solution of naphthofluorescein (4.3 g, 10 mmol) in 50 mL of anhydrous dimethylformamide was added sodium hydride (437 mg, 11 mmol, 60% dispersion in mineral oil) at 0°C. After stirring at 0 °C for half an hour, methoxymethyl chloride (MOMCl) (0.76 mL, 10 mmol) was added to the solution. The resulting mixture was stirred at room temperature overnight, then quenched with water. Then 1N hydrochloric acid was added to the mixture to acidify the solution to pH 2. Then ethyl acetate was added. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography to give compound 9.

[0384] Synthesis of compound 10

[0385]

[0386] To a solution of compound 9 (476 mg, 1 mmol) and pyridine (0.32 mL, 4 mmol) in anhydrous dichloromethane was added trifluoro...

Embodiment 3

[0395] Example 3 - Evaluation of Fluorescence of Quenching Compounds

[0396] Compounds 1-7 obtained in Examples 1 and 2 were each dissolved in DMF to a concentration of 10 mM, and then the solution was diluted to 10 μM with 0.1 M phosphate buffer (pH 7.4). The fluorescence spectrum of the 10 μM compound solution was measured with a Hitachi F2500 fluorimeter, and the photomultiplier tube was set to 700V. The excitation and emission slit widths are both 2.5 nm. Measurements were performed at an excitation wavelength of 600 nm. The results showed that the absolute fluorescence intensities of compounds 1-7 were all less than 10. Therefore, none of compounds 1-7 are practically fluorescent.

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Abstract

Provided herein are compounds or fluorogenic probes which can be used as reagents for measuring, detecting and/or screening ROS or RNS such as peroxynitrite or hypochlorite. Provided also herein are methods that can be used to measure, directly or indirectly, the amount of peroxynitrite or hypochlorite in chemical samples and biological samples such as cells and tissues in living organisms. Specifically, the methods include the steps of contacting the fluorogenic probes disclosed herein with the samples to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite or hypochlorite in chemical and biological samples.

Description

[0001] related earlier application [0002] This application claims priority to US Provisional Patent Application Serial No. 61 / 042,720, filed April 5, 2008. For purposes of US patent practice, the Provisional Application is hereby incorporated by reference in its entirety. technical field [0003] The present invention provides aromatic amine compounds useful as luminescence quenchers and / or fluorescent probes to measure, detect or screen reactive nitrogen species (RNS) such as peroxynitrite or reactive oxygen species (ROS) such as hypochlorite . The present invention also provides a method of producing the aromatic amine compound and a method of using the aromatic amine compound. Background technique [0004] Luminescence is generally the emission of light without deriving energy from the temperature of the emitter. The cause of the luminescence may be chemical, biochemical or crystallographic changes, the motion of subatomic particles, or radiation-induced excitation o...

Claims

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Application Information

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IPC IPC(8): C07D493/10C07D405/00C07D491/00C07D405/14C07D311/82C07D311/00G01N21/64G01N21/77G01N33/533
CPCG01N21/6428C07D493/10C07D307/94G01N33/533
Inventor 杨丹彭涛
Owner VERSITECH LTD
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