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Acridone derivatives as labels for fluorescence detection of target materials

a technology of target materials and derivatives, applied in the field of acridone derivatives, can solve problems such as background fluorescence interference with measuremen

Inactive Publication Date: 2012-01-19
GE HEALTHCARE LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The acridone derivatives provide a set of fluorescent labels with common absorption and emission spectra but distinct fluorescence lifetimes, effectively discriminating labeled biomolecules from background noise, enhancing the sensitivity and specificity of biological assays.

Problems solved by technology

One problem with measurements of fluorescence intensity as a means of detecting and / or measuring the concentration of a fluorescent labelled biomolecule is that background fluorescence may interfere with the measurement.

Method used

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  • Acridone derivatives as labels for fluorescence detection of target materials
  • Acridone derivatives as labels for fluorescence detection of target materials
  • Acridone derivatives as labels for fluorescence detection of target materials

Examples

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Embodiment Construction

[0110]The present examples are provided for illustrative purposes only, and are not to be construed as limiting the present invention as defined by the appended claims. All references given below and elsewhere in the present specification are hereby included herein by reference.

1. O—(N-Succinimidyl)-6-(9-oxo-9H-acridin-10-yl)hexanoate

[0111]

1.1 O-Ethyl-6-(9-oxo-9H-acridin-10-yl)hexanoate

[0112]9-(10H)-Acridone (4.88 g, 25 mmol) was mixed with anhydrous methyl sulfoxide (25 ml) under nitrogen atmosphere and set stirring. After 5 minutes, the resultant yellow slurry was treated with potassium tert-butoxide (3.37 g, 30 mmol) and stirring continued until all the solids had dissolved. Ethyl 6-bromohexanoate (6.7 g, 30 mmol) was then added and the resulting solution stirred under nitrogen for 3 days. At the end of this time the reaction mixture was poured into water (1000 ml) and extracted with ethyl acetate. The organic solution was washed with 0.5M aqueous HCl, then with water, before bei...

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Abstract

Disclosed are methods for assay of an analyte employing acridone dyes having the structure:Z1 and Z2 represent atoms necessary to complete one ring, two fused ring, three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R2, R3, R4 and R5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the groups -E-F and —(CH2—)nY; R1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the groups -E-F and —(CH2—)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a divisional of U.S. patent application Ser. No. 11 / 943,628 filed Nov. 21, 2007, which is a continuation of U.S. patent application Ser. No. 10 / 479,578 filed Dec. 1, 2003, abandoned, which is a filing under 35 U.S.C. §371 and claims priority to international patent application number PCT / GB2002 / 002509 filed May 30, 2002, published on Dec. 12, 2002, as WO 2002 / 099424, which claims priority to patent application number GB 0113435.2 filed Jun. 4, 2001.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to new acridone derivatives having characteristic fluorescence lifetimes that can be used as labels for attachment to and labelling of target materials. The acridone derivatives of the invention may be easily distinguished, one from the other, by virtue of their fluorescence lifetimes and they may be used in multiparameter applications. The invention also relates to assay methods ut...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G01N33/566G01N33/533C07D219/06C07D401/12C09B15/00C09K11/06C12Q1/02C12Q1/26C12Q1/68G01N21/78G01N33/542G01N33/58
CPCG01N33/582C09B15/00
Inventor SMITH, JOHN ANTHONYWEST, RICHARD MARTIN
Owner GE HEALTHCARE LTD
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