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US 5,268,486 AGranted
Method for labeling and detecting materials employing arylsulfonate cyanine dyes
AssigneeCarnegie-Mellon Unversity
InventorsAlan S. Waggoner, Lauren A. Ernst, Ratnakar B. Mujumdar
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Abstract
A luminescent cyanine dye having generally the following structure ##STR1## wherein the dotted lines represent one to three rings having 5 to 6 atoms in each ring. R.sub.3, R.sub.4, R.sub.8 and R.sub.9 groups are attached to the rings. At least one of the R.sub.8 and R.sub.9 groups is a sulfonic acid or sulfonate group and at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.7 groups is a reactive moiety that reacts with amino, hydroxy or sulfhydryl nucleophiles.
Claims8
A water soluble luminescent dye consisting of:
- a cyanine having the structure ##STR12## wherein:
- the dotted lines each represent carbon atoms necessary for the formation of one ring to three fused rings having 5 to 6 atoms in each ring and said R.sub.3, R.sub.4, R.sub.8 and R.sub.9 groups are attached to said rings;
- X and Y are each CH.sub.3 --C--CH.sub.3 ;
- m is an integer selected from the grouping consisting of 1, 2 and 3;
- at least one of said R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.7 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from the group consisting of ##STR13## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R.sub.3, R.sub.4 and R.sub.7, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R.sub.1 and R.sub.2 ;
- and when any one of said R.sub.3, R.sub.4, and R.sub.7 groups is not selected from one said reactive moiety, said remaining R.sub.3, R.sub.4, and R.sub.7 are hydrogen or E--F, a polar group wherein E is a spacer group having the structure --(CH.sub.2).sub.n -- and n of said spacer group=0, 1, 2, 3, or 4, and F is hydroxy, sulfonate, sulfate, carboxylate, or a lower alkyl substituted amino;
- and when any one of said R.sub.1 and R.sub.2 groups is not selected from one said reactive moiety, said remaining R.sub.1 or R.sub.2 are a lower alkyl or said E--F and n of said spacer group=1, 2, 3, or 4;
- at least one said R.sub.8 and R.sub.9 groups is selected from the group consisting of a sulfonic acid and a sulfonate moiety attached directly to said ring for conferring improved luminescence to said dye when in use as compared to a dye which does not have said at least one sulfonic acid or sulfonate moiety;
- and when one of said R.sub.8 or R.sub.9 group is not a sulfonic acid or a sulfonate, said remaining R.sub.8 or R.sub.9 group is a hydrogen.
6 more elements
A water soluble luminescent dye consisting of a cyanine having the structure ##STR16## wherein:
- X and Y are CH.sub.3 --C--CH.sub.3 ;
- m is an integer selected from the group consisting of 1, 2 and 3;
- at least one of said R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.7, R.sub.10 and R.sub.11 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from the group consisting of:
- ##STR17## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R.sub.3, R.sub.4, R.sub.7, R.sub.10 and R.sub.11, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R.sub.1 and R.sub.2 ;
- and when any one of said R.sub.3, R.sub.4, and R.sub.7 groups is not selected from one said reactive moiety, said remaining R.sub.3, R.sub.4, and R.sub.7 are hydrogen or E--F, a polar group wherein E is a spacer group having the structure --(CH.sub.2).sub.n -- and n=0, 1, 2, 3, or 4, and F is hydroxy, sulfonate, sulfate, carboxylate, or lower alkyl substituted amino;
- and when any one of said R.sub.1 and R.sub.2 groups is not selected from one said reactive group, said remaining R.sub.1 and R.sub.2 are lower alkyl or said E--F and n=1, 2, 3, or 4;
- said R.sub.8 and R.sub.9, and said R.sub.10 and R.sub.11 groups when said R.sub.10 and R.sub.11 groups are not said reactive moiety, are selected from the group consisting of hydrogen and a sulfonic acid or sulfonate moiety, wherein at least one of said R.sub.8, R.sub.9, R.sub.10 and R.sub.11 groups is one of said sulfonic acid or said sulfonate moiety attached directly to a ring of said dye for conferring improved luminescence to said dye when in use as compared to a dye which does not have said at least one sulfonic acid or sulfonate moiety.
4 more elements
A water soluble luminescent dye consisting of:
- ##STR18## wherein X and Y are CH.sub.3 --C--CH.sub.3 ;
- m is an integer selected from the group consisting of 1, 2 and 3;
- at least one of said R.sub.1 and R.sub.2 is ##STR19## and the other is selected from the group consisting of ##STR20## --CH.sub.2 CH.sub.2 OH, --(CH.sub.2).sub.k SO.sub.3 where n=1, 2, 3, 4, 5, 6, 7 or 8 and k=2, 3, 4 or 5;
- and
- at least one of said R.sub.8 and R.sub.9 groups is a sulfonate moiety attached directly to a ring of said dye for conferring improved luminescence to said dye when in use as compared to a dye which does not have at least one sulfonic acid or sulfonate moiety;
- and when one of said R.sub.8 and R.sub.9 group is not said sulfonate moiety, said remaining R.sub.8 or R.sub.9 group is a hydrogen.
3 more elements
A water soluble luminescent dye consisting of:
- ##STR21## wherein X and Y are CH.sub.3 --C--CH.sub.3 ;
- m is an integer selected from the group consisting 1, 2 and 3;
- at least one of said R.sub.1 and R.sub.2 is ##STR22## and the other is selected from the group consisting of ##STR23## --CH.sub.2 CH.sub.2 OH, --(CH.sub.2).sub.k SO.sub.3 where n=1, 2, 3, 4, 5, 6, 7, or and k=2, 3, 4, or 5;
- at least two of said R.sub.8, R.sub.9,R.sub.10 and R.sub.11 groups are a sulfonate moiety attached directly to a ring of said dye for conferring improved luminescence to said dye when in use as compared to a dye which does not have at least one sulfonic acid or sulfonate moiety;
- and when any one of said R.sub.8, R.sub.9, R.sub.10 and R.sub.11 groups is not said sulfonate moiety, it is a hydrogen.
2 more elements
A water soluble luminescent dye consisting of:
- ##STR24## wherein X and Y are CH.sub.3 --C--CH.sub.3 ;
- m is an integer selected from the group consisting of 1, 2, and 3;
- at least one of said R.sub.1 and R.sub.2 is ##STR25## and the other is selected from the group consisting of ##STR26## where n=1, 2, 3, 4, 5, 6, 7 or 8 and k=2, 3, 4 or 5;
- at least two of said R.sub.8, R.sub.9 and R.sub.10 groups are a sulfonate moiety attached directly to a ring of said dye for conferring improved luminescence to said dye when in use as compared to a dye which does not have at least one sulfonic acid or sulfonate moiety;
- and when any one of said R.sub.8, R.sub.9 or R.sub.10 is not said sulfonate moiety, it is a hydrogen.
2 more elements
A water soluble luminescent dye consisting of:
- ##STR27## wherein m is an integer selected from the group consisting of 1 and 2 and n=5.
Dependencies are inferred from the claim text.