Chemiluminescent dialkyl-substituted 1,2-dioxetane compounds, methods of synthesis and use
AssigneesBoard of Governors of Wayne State University, Lumigen, Inc.
InventorsArthur Paul Schaap, Hashem Akhavan-Tafti
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Abstract
A chemiluminescent assay method and compositions are described which use a dialkyl-substituted dioxetane which is deprotected to trigger a chemiluminescent reaction. Chemiluminescent 1,2-dioxetane compounds substituted on the dioxetane ring with two nonspirofused alkyl groups which can be triggered by a reagent to generate light are disclosed. Dialkyl-substituted dioxetanes are useful for the detection of triggering agents including enzymes. The enzyme may be present alone or linked to a member of a specific binding pair in an immunoassay, DNA probe assay or other assay where the enzyme is bound to a reporter molecule.
Claims32
A stable 1,2-dioxetane compound of the formula:
- wherein R1 is selected from alkyl and cycloalkyl groups containing 1 to 12 carbon atoms which can additionally contain heteroatoms, wherein R2 is a meta-phenyl group substituted by the OX group in the position meta to the dioxetane ring, wherein R3 and R4 are selected independently from branched alkyl and cycloalkyl groups containing 3 to 8 carbons atoms which can additionally contain heteroatoms and which provide thermal stability, and wherein X is a chemically labile group selected from the group consisting of trialkylsilyl and PO32− salt, which can be removed by a reagent selected from the group consisting of enzymes, electron donors, organic and inorganic bases, nucleophilic reagents and reducing agents to form an unstable oxide intermediate 1,2-dioxetane compound which decomposes to form light and two carbonyl compounds of the formula:
A dioxetane compound having the formula:
A dioxetane compound having the formula:
A dioxetane compound having the formula:
A dioxetane compound having the formula:
A 1,2-dioxetane compound of the formula:
- wherein R1 represents a substituted or unsubstituted alkyl or cycloalkyl group;
- R3 and R4 each represent, individually, a substituted or unsubstituted branched alkyl or cycloalkyl group;
- and X represents trialkylsilyl or a PO32− salt group.
Dependencies are inferred from the claim text.