Wayne State University

Tropix, Inc.

Lumigen, Inc.

Other

Arthur P Schaap

Hashem Akhavan-Tafti

Louis J Romano

Irena Y Bronstein

Jaidev S Goudar

Renuka DeSilva

Hashem Akhavan-Jaffi

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.

Chemiluminescent dialkyl-substituted 1,2-dioxetane compounds, methods of synthesis and use

A method and compositions including a 1,2-dioxetane and a fluorescent compound is described. In particular, enzymatic triggering of a triggerable 1,2-dioxetane admixed with a surfactant and the fluorescent compound attached to a hydrocarbon to provide a co-surfactant in a micelle or other structure providing close association of these molecules is described. The method and compositions are useful in immunoassays and in DNA probes used for various purposes.

Method and compositions providing enhanced chemiluminescence from

Chemiluminescent dialkyl-substituted 1,2-dioxetanes, methods of

Method providing enhanced chemiluminescence from 1,2-dioxetanes

Alkene precursors for preparing dialkyl-substituted dioxetanes. The dioxetanes are useful for the detection of triggering agents including enzymes.

Alkene precursors for preparing chemiluminescent dialkyl-substituted

Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an `activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.

1,2-dioxetane compounds as chemiluminescent labels for organic and

Stable, enzymatically triggered chemiluminescent 1,2-dioxetanes with improved water solubility are provided. Dioxetanes further substituted with two or more water-solubilizing groups disposed on the dioxetane structure provide superior performance by eliminating the problem of reagent carryover when used in assays performed on capsule chemistry analytical systems. Compositions comprising a dioxetane with two or more water-solubilizing groups, a non-polymeric cationic surfactant enhancer and optionally a fluorescer, for providing enhanced chemiluminescence are also provided.

Di-substituted 1,2-dioxetane compounds having increased water solubility

Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.

Alkene intermediates for preparing 1,2-dioxetane compounds

Dioxetanes which couple with organic and biological molecules of the formula: ##STR1## wherein X is a leaving group which is removed by an activating agent other than an enzyme which is removed by an activating agent to produce light, wherein A is a coupling substituent, Ar is a substituent selected from the group consisting of phenyl and naphthyl to provide a label are described. R.sub.1 is an optional linker substituent and can have between 1 and 30 carbon atoms with some of the carbon atoms being oxygen, sulfur, nitrogen or phosphorus. Ar as phenyl is preferred. The dioxetane coupled molecules are useful in assays of all types where luminescence can be used as an indicator.

1,2-Dioxetane compounds as chemiluminescent labels for organic and

Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.

Chemiluminescent 1,2-dioxetane compounds

Novel alkene intermediates useful in the preparation of 1,2-dioxetanes.

Alkene intermediates for preparing 1,2-dioxetanes

4-(3-beta-D-galactopyranosylphenyl)-4-methoxyspiro[1,2-dioxetane-3,2'-adama ntane] which is useful in various chemiluminescent assays.

1,2-dioxetane compound

Alkene adamantane compounds useful as intermediates for producing the corresponding 1,2-dioxetanes which are useful in chemiluminescent assays.

Alkene adamantane intermediates and the corresponding 1,2-dioxetanes

Triggerable dioxetanes with a fluorescent substituent bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are carbon containing groups and wherein one of R.sub.1, R.sub.2 and R.sub.3 is a tethered fluorescent substitutent. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.

Growing community of inventors

Detroit, MI, United States of America

Arthur P Schaap