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Chemical probe compounds that become fluorescent upon reduction, and methods for their use

a technology of chemical probe compounds and fluorescent compounds, applied in the field of quenching chemical stain compounds, to achieve the effect of reducing the quenching ability

Inactive Publication Date: 2006-09-07
MOLECULAR PROBES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These materials are not generally used to measure the oxidative function of cells, as atmospheric oxygen can oxidize them as well.

Method used

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  • Chemical probe compounds that become fluorescent upon reduction, and methods for their use
  • Chemical probe compounds that become fluorescent upon reduction, and methods for their use
  • Chemical probe compounds that become fluorescent upon reduction, and methods for their use

Examples

Experimental program
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Effect test

example 1

Preparation of Compound (5)

[0045] A mixture of 40 mg compound (1), 60 mg 2-(2-aminoethylthio)methylanthraquinone, and 45 microliters triethylamine was stirred in 1 mL dimethylformamide overnight at room temperature. Product compound (5) was purified by column chromatography on silica gel with 4:4:3:1 ethyl acetate: chloroform: methanol: acetic acid.

example 2

Preparation of Compound (6)

[0046] A mixture of 4.4 g of 2-methyl-1,4-napthoquinone and 11.9 g of 1-tBoc-piperazine was heated in 90 mL of a methanol / dichloromethane (1:1, v / v) solvent mixture at about 45° C. for 24 hours. The solvent was evaporated and the crude product was purified on a silica gel column to yield 1.08 g of desired intermediate. Trifluoroacetic acid (1 mL) was added to 100 mg of this tBoc-protected piperazine in 5 mL of dichloromethane, and after one hour at room temperature, all of the volatile components were removed and the product compound (6) was used “as is” without further purification.

example 3

Preparation of Compound (7)

[0047] Triethylamine (0.21 mL) was added to a mixture of 70 mg of compound (3) and 0.28 mmole of compound (6) in 5 mL of dichloroethane, and the resulting reaction mixture was heated at 55-60° C. for one hour. The reaction was cooled to room temperature and volatile components were evaporated. The crude product compound (7) was purified using silica gel column chromatography with 2:2:1 ethyl acetate: chloroform: methanol.

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Abstract

Chemical stain compounds containing a fluorophore and a reducible quenching unit are disclosed. The reducible quenching unit quenches the fluorophore while in its oxidized state. Upon reduction, the quenching properties of the quenching unit are diminished or eliminated. The chemical compounds can be used in a variety of applications, including the detection of bacterial cells, monitoring the electron transport chain function of bacterial cells, monitoring the oxidation state of non-biological systems, and assaying the effectiveness of antibacterial or antimicrobial agents.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] The present application claims priority to U.S. Provisional Patent Application Ser. No. 60 / 657,944 filed Mar. 1, 2005, the contents of which are incorporated herein by reference.FIELD OF THE INVENTION [0002] The invention relates to quenched chemical stain compounds that can be reduced to a fluorescing form, and methods for their use. DESCRIPTION OF RELATED ART [0003] Oxidation and reduction are natural metabolic functions of living cells. Methods and materials for the detection of the oxidative states of cells have been desirable for some time, as they allow researchers to achieve a better understanding of the conditions within cells or cell compartments. Various methods have been used to date. [0004] One approach is to use a chemical probe that is not fluorescent outside of the cell, but which becomes oxidized to a fluorescent derivative once it enters the cell. Dihydrorhodamine and dihydroethidium are examples of such chemicals that ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C12Q1/18G01N33/18C07D417/02
CPCC07D211/62C07D295/112C07D417/06C07D417/14G01N33/582C12Q1/04C12Q1/18G01N33/52C09B23/04C07D401/14G01N21/643G01N33/1806G01N2021/6432
Inventor CHEUNG, CHING-YINGGRAY, DIANE R.YUE, STEPHEN T.
Owner MOLECULAR PROBES
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