Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetan

Details Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetan Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetan

1991-12-12

1994-07-19

Yarbrough, Amelia Burgess

Chemistry: molecular biology and microbiology

Measuring or testing process involving enzymes or...

Involving nucleic acid

435 21, 435968, 435810, 436800, 436808, 436172, 935 78, C12Q 168

Patent

active

053309006

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## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, 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; and
R.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sub.1 and R.sub.2 represent individual substituents the R.sub.2 substituent is aromatic, heteroaromatic, or an unsaturated substituent in conjugation with an aromatic ring, and that at least one of R.sub.1 and R.sub.2 is, or R.sub.1 and R.sub.2 taken together are, an enzymatically cleavable labile group-substituted fluorescent chromophore group that produces a luminescent substance when the enzymatically cleavable labile substituent thereof is removed by an enzyme.
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.

REFERENCES:
patent: 4931223 (1990-06-01), Bronstein et al.
patent: 4952707 (1990-08-01), Edwards et al.
patent: 4962192 (1990-10-01), Schaap
patent: 4978614 (1990-12-01), Bronstein et al.
patent: 5032381 (1991-07-01), Bronstein et al.

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