Patent ID: 6013802
Filing Date: 2000-01-11
Classification: C09K,G01N

Abstract:
A compound containing:a metal ion-binding moiety, M, having two pyridyl rings, of the formula ##STR8## wherein pyridyl ring substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 perfluoroalkyl, halogen, CN, sulfonic acid, salt of sulfonic acid, amino, salt of amino, alkylamino having 1-6 carbons, dialkylamino having 2-12 carbons; carboxy, carboxyalkyl having 2-7 carbons, carboxyalkoxy having 2-7 carbons, carboxyalkylthio having 2-7 carbons, carboxyalkoxy having 2-7 carbons, or a 1-(acyloxy)alkyl ester of any such carboxy, such ester having 2-7 carbons; or aryl, or heteroaryl; or --L--F.sub.L ;or any two adjacent substituents of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.8, taken into combination, form a fused six-membered aromatic ring, such that no more than one fused ring is bound to each pyridyl ring, and where said fused rings are optionally and independently further substituted by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 perfluoroalkyl, CN, sulfonic acid, salt of sulfonic acid, amino, alkylamino having 1-6 carbons, dialkylamino having 2-12 carbons; carboxy, carboxyalkyl having 2-7 carbons, carboxyalkoxy having 2-7 carbons, carboxyalkylthio having 2-7 carbons, or a 1-(acyloxy)alkyl ester of any such carboxy, such ester having 2-7 carbons; or --L--F.sub.L ; andK is a single covalent bond, orK is --(CR.sup.11.sub.2).sub.a --NR.sup.13.sub.b --(CR.sup.12.sub.2).sub.c --,wherein a, b and c are each 0 or 1, provided that when b=1, a+c must equal 0 or 2;each R.sup.11 and R.sup.12 is optionally and independently H, or C.sub.1 -C.sub.6 alkyl;R.sup.13 is H, C.sub.1 -C.sub.6 alkyl, --L--F.sub.L, or phenyl that is optionally further substituted by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, NO.sub.2, C.sub.1 -C.sub.6 perfluoroalkyl, halogen, CN, sulfonic acid, salt of sulfonic acid, amino, alkylamino having 1-6 carbons, dialkylamino having 2-12 carbons; carboxy, carboxyalkyl having 2-7 carbons, carboxyalkoxy, or a 1-(acyloxy)alkyl ester of any such carboxy, such ester having 2-7 carbons; or --L--F.sub.L ; orK is ##STR9## wherein R.sup.16, R.sup.17, and R.sup.18 are independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, NO.sub.2, C.sub.1 -C.sub.6 perfluoroalkyl, halogen, CN, sulfonic acid, salt of sulfonic acid, amino, alkylamino having 1-6 carbons, dialkylamino having 2-12 carbons; carboxy, carboxyalkyl having 2-7 carbons, carboxyalkoxy having 2-7 carbons, carboxyalkylthio having 2-7 carbons, or a 1-(acyloxy)alkyl ester of any such carboxy, such ester having 2-7 carbons; or aryl, or heteroaryl, or --L--F.sub.L ; orK is a formal single bond, and R.sup.4 and R.sup.5 when taken in combination are --CR.sup.9 .dbd.CR.sup.10 --, forming a phenanthroline moiety, wherein R.sup.9 and R.sup.10 are independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 perfluoroalkyl, CN, sulfonic acid, salt of sulfonic acid, amino, alkylamino having 1-6 carbons, dialkylamino having 2-12 carbons; carboxy, carboxyalkyl having 2-7 carbons, carboxyalkoxy having 2-7 carbons, carboxyalkylthio having 2-7 carbons; or a 1-(acyloxy)alkyl ester of any such carboxy, such ester having 2-7 carbons; or --L--F.sub.L ; and the remaining ring substituents R.sup.1, R.sup.2, R.sup.3, R.sup.6, R.sup.7, and R.sup.8 are as defined above;such that at least one but not more than two substituents on said metal ion-binding moiety is --L--F.sub.L ; whereineach F.sub.L is independently a fluorescein, a rhodol, a rosamine or a rhodamine fluorophore that is attached to said metal-binding moiety by L, where each L is independently a single bond or a covalent linkage that is 9 or fewer non-hydrogen atoms in length.