Improved chemiluminescent 1,2-dioxetanes

Details Improved chemiluminescent 1,2-dioxetanes Improved chemiluminescent 1,2-dioxetanes

C - Chemistry, Metallurgy

12

Q

C12Q 1/42 (2006.01) C07C 43/178 (2006.01) C07C 43/225 (2006.01) C07C 43/23 (2006.01) C07C 43/315 (2006.01) C07C 45/67 (2006.01) C07C 47/565 (2006.01) C07C 47/575 (2006.01) C07C 65/03 (2006.01) C07C 65/21 (2006.01) C07C 69/017 (2006.01) C07C 69/63 (2006.01) C07C 205/35 (2006.01) C07C 205/37 (2006.01) C07C 205/44 (2006.01) C07C 217/76 (2006.01) C07C 217/84 (2006.01) C07C 233/18 (2006.01) C07C 271/28 (2006.01) C07C 271/58 (2006.01) C07D 321/00 (2006.01) C07F 7/08 (2006.01) C07F 9/12 (2006.01) C07F 9/40 (2006.0

Patent

CA 2139348

Novel 1,2-dioxetanes with improved chemiluminescent properties, such as signal intensity, S/N ratio, T1/2, etc. are provided by spiroadamantyl 1,2-dioxetanes, wherein the remaining carbon atom of the ring bears an alkoxy, aryloxy, or arylalkoxy substituent, and either a phenyl or naphthyl ring, this aromatic ring bearing, at the meta position on the phenyl group, or a non-conjugated position on the naphthyl ring, an OX moiety wherein X is an enzyme-clevable group, which when removed from the dioxetane, leaves the oxyanion which decomposes with chemiluminescence, the aryl ring further bearing an electron-active substituent Z. The nature and placement of the Z substituent, at a position not adjacent the point of attachment to the dioxetane ring, strongly influences the properties of the dioxetane. Assays, as well as kits for the performance of those assays, include the dioxetane, an enzyme capable of cleaving the X group, and in certain cases, membranes and chemiluminescent enhancement agents.

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