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US 5,543,524 AGranted
Chemiluminescent acridinium salts
AssigneeAbbott Laboratories
InventorsPhillip G. Mattingly, Larry G. Bennett
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Abstract
Acridinium sulfonylamides and isomers, such as phenanthridinium sulfonylamides, may be employed in applications including chemiluminmescent immunoassays. Methods for synthesis of these compounds include contacting an amine with a sulfonylhalide to form a sulfonamide and acylating with an activated carboxylic acid of an acridine or isomer thereof. The N-sulfonyl-9-acridinium carboxamide and isomers may be conjugated to antigens, haptens, antibodies, and nucleic acids for use in chemiluminescent assays.
Claims1
A method for preparation of a chemiluminescent compound comprising the steps of:
- contacting an amine identified by the formula
- R--X.sup.3 --NH.sub.2
- with a sulfonylhalide identified by the formula
- W--SO.sub.2 --R'--X.sup.2
- in an inert solvent in the presence of base to form a sulfonamide anion and metal ion identified by the formulas
- M+X.sup.3 --R--N.sup.- --SO.sub.2 --R'--X.sup.2 ;
- and
- acylating with an activated 9-acridinecarboxylic acid identified by the formula ##STR17## wherein R, R' and R" are independently selected from the group consisting of:
- alkyl, aryl, alkylene, substituted alkyl, substituted alkylene and substituted aryl, alkoxy, aryloxy, halo, amino, protected amino, substituted amino hydroxy, protected hydroxy, oxo, thio, imino, mercapto groups;
- and alkyl, aryl, alkylene substituted alkyl, substituted alkylene and substituted aryl groups comprising a heteroatom selected from the group consisting of nitrogen, phosphorus, sulfur and oxygen with the proviso that R--X.sup.3, R'--X.sup.2 and R"--X.sup.1 may independently be hydrogen;
- wherein X.sup.1, X.sup.2, and X.sup.3 are independently members of the group consisting of hydrogen, carboxy, carboalkoxyl, carboxamido, carboaryloxy, cyano, carboximido, isocyanato, isothiocyanato, sulfo, sulfonyl halide, carbonyl halide, N-carboxysuccinimide and N-maleimide groups;
- wherein Y is an appropriate counter ion;
- wherein W is selected from the group consisting of chloro and fluoro groups;
- and
- wherein M is selected from the group consisting of Li, Na and K;
- and
- wherein Z is selected from the group consisting of halo, imidazolo, N-hydroxysuccinimidyl and azido groups.
14 more elements
Dependencies are inferred from the claim text.