Chemiluminescent 1,2-dioxetane compounds
AssigneeTropix, Inc.
InventorsArthur Paul Schaap, Irena Y. Bronstein
Life of this patent
Estimating the term…
Abstract
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.
Claims29
The method for generating light which comprises:
- (a) providing a stable 1,2-dioxetane of the formula ##STR46## wherein ArOX represents an aryl group substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove X by an activating agent so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula ##STR47## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced;
- and
- (b) decomposing the stable 1,2-dioxetane with the activating agent.
The method for generating light which comprises:
- (a) providing a stable 1,2-dioxetane compound of the formula ##STR48## wherein R.sub.1 and R.sub.2 together and R.sub.3 and R.sub.4 together can be joined as spirofused alkylene and aryl rings, wherein at least one of R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 is an aryl group substituted with an X-oxy group which forms an unstable oxide intermediate 1,2 dioxetane compound when triggered to remove X by an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula:
- ##STR49## wherein those of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 which are unsubstituted by an X-oxy group are carbon containing organic groups which provide stability for the stable 1,2-dioxetane compound and wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate;
- and
- (b) decomposing the stable 1,2-dioxetane with the activating agent.
The method for generating light which comprises:
- (a) providing a stable dioxetane compound of the formula:
- ##STR50## wherein R.sub.1 is selected from alkyl, alkoxy, aryloxy dialkylamino, trialkyl or aryl silyloxy and aryl groups including spirofused aryl groups with R.sub.2, wherein R.sub.2 is an aryl group which can include R.sub.1 and is substituted with an X-oxy group which forms an unstable oxide intermediate 1,2-dioxetane compound when triggered to remove X by an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and electron donors so that the unstable 1,2-dioxetane compound decomposes to form light and two carbonyl containing compounds of the formula:
- ##STR51## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate and wherein R.sub.3 and R.sub.4 are selected from aryl and alkyl groups which can be joined together as spirofused polycyclic alkyl and polycyclic aryl groups;
- and
- (b) decomposing the stable 1,2-dioxetane with the activating agent.
The method of claim 8 wherein the method is performed as part of an immunoassay.
A method for generating light in a chemiluminescent assay using an enzyme from a biological source which comprises:
- (a) providing a compound of the formula:
- ##STR52## wherein R.sub.1 and R.sub.2 taken together are a spirofused polycyclic aryl group having an aryl ring substituted with an X-oxy group wherein X is removeable by enzymatic triggering ahd R.sub.3 and R.sub.4 taken together are an adamantyl group;
- and
- (b) triggering the compound to generate light using an enzyme from a biological source.
A method for generating light in a chemiluminescent assay using an enzyme from a biological source which comprises:
- (a) providing a compound of the formula:
- ##STR53## wherein R.sub.1 is methoxy, R.sub.2 is an aryl group substituted with an X-oxy group wherein X is removable by enzymatic triggering and R.sub.3 and R.sub.4 taken together are an adamantyl group;
- and
- (b) triggering the compound to generate light using an enzyme from a biological source.
In an immunoassay method wherein there is an optically detectable reaction, the improvement wherein said optically detectable reaction includes the reaction, with an enzyme, of a dioxetane having the formula ##STR54## where T is an adamantyl group;
- Y is naphthyl;
- X is methoxy;
- and Z is an enzyme-cleavable group,
- so that said enzyme cleaves said enzyme-clearable group from said dioxetane to form a negatively charged substituent bonded to said dioxetane, said negatively charged substituent causing said dioxetane to decompose to form a luminescent substance comprising said group Y of said dioxetane.
Dependencies are inferred from the claim text.