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US 5,669,819 AGranted
Chemiluminescent phenanthridinium
AssigneeAbbott Laboratories
InventorsPhillip Gregory Mattingly, Larry Gene Bennett
Life of this patent
Estimating the term…
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.
Claims14
A chemiluminescent conjugate comprising an antibody conjugated to a chemiluminescent compound of the formula:
- ##STR17## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the antibody is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), --C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR18## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
A chemiluminescent conjugate comprising an antigen conjugated to a chemiluminescent compound of the formula:
- ##STR19## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the antigen is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), (--C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR20## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
A chemiluminescent conjugate formed by a polynucleotide conjugated to a chemiluminescent compound of the formula:
- ##STR21## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the polynucleotide is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), (--C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR22## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
A chemiluminescent conjugate comprising a non-antibody, binding protein conjugated to a chemiluminescent compound of the formula:
- ##STR23## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the non-antibody, binding protein is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), (--C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR24## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
A chemiluminescent conjugate comprising a hapten conjugated to a chemiluminescent compound of the formula:
- ##STR25## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the hapten is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), (--C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR26## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- p2 one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
A chemiluminescent conjugate comprising a small molecular weight analyte which binds to a binding protein conjugated to a chemiluminescent compound of the formula:
- ##STR27## wherein R, R', R", X.sup.1, X.sup.2 and X.sup.3 independently comprise substituents which do not interfere with chemiluminescence measurement, linkage to the small molecular weight analyte is through one of X.sup.1, X.sup.2 and X.sup.3, and wherein Y.sup.- is an anion with the proviso that R--X.sup.3 R'--X.sup.2 and R"--X.sup.1 may be hydrogen,
- wherein X.sup.1, X.sup.2 and X.sup.3 are independently members of the group consisting of hydrogen, (--CO.sub.2 H), (--C(.dbd.O)OZ.sup.1) wherein Z.sup.1 is alkyl, (--C(.dbd.O)NZ.sup.2 Z.sup.3) wherein Z.sup.2 or Z.sup.3 is H, alkyl or aryl, (--C(.dbd.O)OZ.sup.4) wherein Z.sup.4 is aryl, (--CN), (--C(.dbd.O)N(Z.sup.5)--C(.dbd.O)--Z.sup.5) wherein Z.sup.5 is H, alkyl or aryl, (F, Cl, Br, or I), (--N.dbd.C.dbd.O), (--N.dbd.C.dbd.S), (--SO.sub.3.sup.-), sulfonyl halide (--SO.sub.2 Z.sup.6) wherein Z.sup.6 is (Cl or F), (--C(.dbd.O)--Z.sup.7) wherein Z.sup.7 is (F, Cl, or Br), ##STR28## groups;
- wherein R independently comprises a member selected from the group consisting of alkylene, alkenylene and substituted alkylene groups and wherein R' and R" independently comprise a member selected from the group consisting of alkylene, arylene, alkenylene, substituted alkylene, and substituted arylene groups, such that:
- one or more hydrogens or open valences of said member is replaced by an alkyl, aryl, alkylene, alkenylene, substituted alkyl, substituted alkylene, substituted aryl, alkoxy, aryloxy, halo, nitro, amino, protected amino, substituted amino, hydroxy, protected hydroxy, oxo, thio, imino, mercapto or substituted mercapto group;
- or such that one or more carbon atoms of the member is replaced by a heteroatom.
2 more elements
Dependencies are inferred from the claim text.