Dioxetanes for use in assays

Details Dioxetanes for use in assays Dioxetanes for use in assays

1990-04-13

1992-02-18

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549332, 548113, 536 181, C07D49310, C07F 9665

Patent

active

050896300

ABSTRACT:
A dioxetane that includes a fluorescent chromophore spiro-bound at the 4-carbon of the dioxetane. The dioxetane has the formula ##STR1## where X is CR.sub.7 R.sub.8, O, S, or N-R (where each R.sub.7, R.sub.8, and R, independently, is H, alkyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, cycloheteroalkyl, aralkyl, alkaryl, or an enzyme cleavable group), and each R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, andR.sub.6, independently, is H, an electron-withdrawing group, an electron-donating group, heteroaryl, or an enzyme cleavable group, or groups R.sub.1 -R.sub.6 together form a ring, and T is a substituted or unsubstituted aryl, polyaryl, cycloalkylidene or polycycloalkylidene group spiro-bound at the 3-carbon of the dioxetane.
The dioxetane can be decomposed by direct cleavage of the dioxetane 0--0 bond or by cleavage of an enzyme cleavable group bonded to the dioxetane to form a luminescent substance that includes the coumarin portion of the dioxetane.
The dioxetanes are used in an assay to detect a member of a specific binding pair or an enzyme.

REFERENCES:
patent: 4857652 (1989-08-01), Schaap
Adam et al., Agnew, Chem. Int. Ed. Engl. 26:796 (1987).
Schaap et al., Tetrahedron Lett. 28:1159 (1987).

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