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Modified nucleic acid-binding cyanine dyes for detection of reactive oxygen species

A dye compound, structural formula technology, applied in the direction of organic dyes, methine/polymethine dyes, analytical materials, etc., can solve the problems of high toxicity, low emission wavelength, limited application and so on

Active Publication Date: 2016-07-13
LIFE TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, DHE has limited applicability due to its spontaneous autoxidation, rapid photobleaching, high toxicity, and multiple reaction products with ROS
Furthermore, the lower emission wavelength of DHE makes its in vivo application problematic
Dihydrorhodamine (DHR), another vat dye that has been investigated for the detection of ROS, suffers from a high oxidation rate, thus limiting its application
These probes (often requiring time-consuming and expensive multi-step synthetic procedures) undergo rapid hydrolysis, thereby limiting their applications

Method used

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  • Modified nucleic acid-binding cyanine dyes for detection of reactive oxygen species
  • Modified nucleic acid-binding cyanine dyes for detection of reactive oxygen species
  • Modified nucleic acid-binding cyanine dyes for detection of reactive oxygen species

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0268] Example 1: (Z)-2-((2-butyl-1-phenylquinoline-4(1H)-ylidene)methyl)-3-methyl-2,3-di Synthesis of Hydrobenzo[d]thiazole (1)

[0269]

[0270] To (Z)-2-((2-butyl-1-phenylquinolin-4(1H)-ylidene)methyl)-3-methylbenzo[d]thiazol-3-ium iodide ( To a solution of 350 mg, 0.636 mmol) in methanol (15 mL), sodium borohydride (96 mg, 2.54 mmol) was added slowly, and the mixture was kept stirring at ice-water bath temperature for 30 min. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (2x50 mL). The separated organic layer was subjected to Na 2 SO 4 Dry and filter. After evaporation of the solvent, the crude product was purified by column chromatography on silica gel eluting with 2% ethyl acetate in hexanes to afford the desired product ( 1 , 225 mg, 83% yield). TLC: R f =0.45 (silica gel, 5% ethyl acetate in hexane).

Embodiment 2

[0271] Example 2: (Z)-2-((2-butyl-1-phenylquinoline-4(1H)-ylidene)methyl)-3-methyl-2-deuterium-3- Synthesis of Hydrobenzo[d]thiazole (2)

[0272]

[0273] To (Z)-2-((2-butyl-1-phenylquinolin-4(1H)-ylidene)methyl)-3-methylbenzo[d]thiazol-3-ium iodide ( To a solution of 100 mg, 0.18 mmol) in methanol (5 mL), sodium borodeuteride (22 mg, 0.53 mmol) was added slowly, and the mixture was kept stirring at ice-water bath temperature for 30 min. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2x30 mL). The separated organic layer was subjected to Na 2 SO 4 Dry and filter. After evaporation of the solvent, the crude product was purified by column chromatography on silica gel eluting with 2% ethyl acetate in hexanes to afford the desired product ( 2 , 50 mg, 65% yield). TLC: R f =0.43 (silica gel, 5% ethyl acetate in hexane).

Embodiment 3

[0274] Example 3: (Z)-3-methyl-2-((1-propylquinoline-4(1H)-ylidene)methyl)-2,3-dihydrobenzo[d] Synthesis of Thiazole (3)

[0275]

[0276] with the above compound 1 A similar procedure described in the Examples, from (Z)-3-methyl-2-((1-propylquinolin-4(1H)-ylidene)methyl)benzo[d]thiazole-3 -onium tosylate and sodium borohydride preparation compound 3 .

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Abstract

Disclosed herein are compounds, compositions, methods, and kits for detecting reactive oxygen species (ROS) by conventional fluorescence microscopy, fluorescence spectroscopy, flow cytometry, and / or high content imaging. The compounds disclosed herein are novel reduced nucleic acid binding cyanine dyes, which dyes are probes for detecting ROS and measuring oxidative stress in cells either in vitro and / or in vivo. Also described herein are processes for preparing novel reduced dyes, i.e., ROS probes, for use in the disclosed compositions, methods and kits.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of priority to US Provisional Application Serial No. 61 / 617,862, filed March 30, 2012, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to probes useful for the detection of reactive oxygen species (ROS), in particular reduced nucleic acid-binding cyanine dye probes, and the use of such probes in vitro or in vivo. Background technique [0004] Oxidative stress arises from an imbalance between the production of reactive oxygen species (ROS) and the cell's ability to scavenge such free radicals. Oxidative stress can be caused by many different intrinsic and extrinsic pathways, mediated by mitochondrial respiration or by membrane-bound NADPH oxidase. ROS play an important role in the progression of several diseases including, but not limited to, inflammation, atherosclerosis, aging and age-related degenerative disorders....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/02C09B23/04C09B23/06G01N33/533G01N33/58
CPCG01N33/84C07D417/06C09B23/02C09B23/04C09B23/06G01N33/52
Inventor 胡义镇陈爱梅H.C.康K.吉B.曼达维利
Owner LIFE TECH CORP
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