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Electrochemiluminescence from acridan compounds

a technology of acridine and acridine, which is applied in the field of electrochemiluminescence, can solve the problems that ph is not particularly useful in immunoassays and nucleotide assays, and achieve the effect of robust labels

Inactive Publication Date: 2007-03-15
LUMIGEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

[0013] Unlike art-known methods of generating luminescence electrochemically using an acridinium ester, the reaction does not involve the electrochemical generation of H2O2 or superoxide. The acridan compounds used in the present methods are significantly more stable that the corresponding acridinium compounds and should provide more robust labels.

Problems solved by technology

(J. S. Littig and T. A. Neeman, Anal. Chem., 1992, 64, 1140-1144) This pH is not particularly useful for immunoassays and nucleotide assays.

Method used

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  • Electrochemiluminescence from acridan compounds
  • Electrochemiluminescence from acridan compounds
  • Electrochemiluminescence from acridan compounds

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examples

[0042] 2′,6′-Difluorophenyl 10-methylacridan-9-carboxylate (DMC) was made by the method disclosed in U.S. Pat. No. 5,593,845. Stock solutions of DMC were prepared in 1:1 ethanol-dioxane. All work was carried out in 10 mM Tris buffer, pH 8.0, containing 0.1 M NaCl, 10 mM, 1 mM EDTA and 0.025% Tween-20 unless otherwise stated. Stock solutions of DMC were dissolved in buffer to give a final solvent concentration of 0.25%. Light was excluded from all DMC solutions.

[0043] A second acridan compound 2′,3′,6′-difluorophenyl 10-methylacridan-9-carboxylate (Lumigen PS-3) was made as described in U.S. Pat. No. 5,593,845. Stock solutions were prepared in 1:1 ethanol: 1,4-dioxane. The acridan phosphate compound 9-(Phenylthiophosphoryloxymethylidene)-10-methyl-acridan, disodium salt (APS-2) was prepared as described in U.S. Pat. No. 6,045,727.

[0044] Equipment. Transparent electrodes were made from ITO coated glass from Balzer Ltd. (Buckinghamshire, UK) that had a sheet resistance of 200 W / ® (oh...

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Abstract

Methods are disclosed for producing electrochemiluminescence by electrochemically oxidizing an acridan compound at an electrode in the presence of a peroxide. Maintaining a sufficiently positive potential results in continuous oxidation of the acridan compound to an acridinium compound which reacts with peroxide to produce the luminescence. Light emission can be reversibly and repeatedly cycled on and off by sweeping the potential between two values. The acridan compounds can be provided with a labeling group for linking to an analyte or analyte binding partner. The present electrochemiluminescent reaction can find use in assay methods for detecting analytes by immunoassays and nucleic acid assays.

Description

[0001] This application claims priority from Provisional U.S. Application No. 60 / 214,178, filed Jun. 26, 2000.FIELD OF THE INVENTION [0002] The present invention relates to the field of electrochemiluminescence which is the production of luminescence by an electrochemical reaction. In particular the present invention relates to methods of producing electrochemiluminescence from acridan compounds. The present electrochemiluminescent reaction can find use in assay methods for detecting analytes. The acridan compounds can be provided with a labeling group for linking to an analyte or analyte binding partner. BACKGROUND OF THE INVENTION [0003] Electrochemiluminescence (ECL) has received widespread attention during the previous decade, especially in the field of chemical analysis. It combines the well known sensitivity of chemiluminescence (CL) with the precise control over the time and position of light emitting reactions afforded by electrochemistry. As an alternative approach for cond...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G01N33/50
CPCC07D219/14G01N21/66G01N21/76Y10S436/805Y10S436/80Y10S435/963G01N33/533
Inventor AKHAVAN-TAFTI, HASHENWILSON, ROBERTSCHIFFRIN, DAVID JORGE
Owner LUMIGEN