Chemiluminescent 3-(substituted Adamant-2'-Ylidene) 1,2-dioxetanes
AssigneeTropix, Inc.
InventorsIrena Bronstein, Brooks Edwards, Rouh-Rong Juo
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Abstract
Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 4' methylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.
Claims3
A compound of the formula ##STR21## wherein R.sub.1 is O(CH.sub.2).sub.n CH.sub.3, wherein n is an integer of 0-19,
- R.sub.2 is ##STR22## wherein Z is a moiety selected from the group consisting of a phosphate, galactoside, acetate, 1-phospho-1,3-diacylglyceride, 1-thio-D-glucoside, adenosine triphosphate, adenosine diphosphate adenosine monophosphate, adenosine, .alpha.-D-glucoside, .beta.-D-glucoside, .alpha.-D-mannoside, .beta.-D-mannoside, .beta.-D-fructofuranoside, .beta.-D-glucosiduronate, p-tolunesulfonyl-L-arginine ester, and p-toluenesulfonyl-1-arginine amide.
A compound of the formula ##STR23## wherein X and X.sup.1 each represent individually, hydrogen, a hydroxyl group, a halo substituent, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen,
- wherein n=0-19,
- wherein Z is a moiety selected from the group consisting of a phosphate, galactoside, acetate, 1-phospho-2,3-diacylglyceride, 1-thio-D-glucoside, adenosine triphosphate, adenosine diphosphate adenosine monophosphate, adenosine, .alpha.-D-glucoside, .beta.-D-glucoside, .alpha.-D-mannoside, .beta.-D-mannoside, .beta.-D-fructofuranoside, .beta.-D-glucosiduronate, p-toluenesulfonyl-L-arginine ester, and p-toluenesulfonyl-1-arginine amide, and
- Q is selected from the group consisting of C.sub.1-20 alkyl, C.sub.1-20 aryl, C.sub.1-20 aralkyl, OSiR.sup.3 wherein R.sup.3 is C.sub.1-6 alkyl C.sub.1-6 alkoxy, C.sub.1-12 alkoxyalkyl, --OR.sup.4 wherein R.sup.4 is aralkyl of up to 20 carbon atoms, --SO.sub.2 R.sup.5 wherein R.sup.5 is methyl, phenyl or NHC.sub.6 H.sub.5, a halogen, a hydroxy moiety, a carboxy moiety and a phosphorloxy group.
Dependencies are inferred from the claim text.