Method for labeling and detecting materials employing arylsulfonate cyanine dyes
First Claim
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1. A water soluble luminescent dye ponsisting of:
- a cyanine having the structure ##STR11## 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 R3, R4, R8 and R9 groups are attached to said rings;
X and Y are S;
m is an integer selected from the grouping consisting of 1, 2 and 3;
at least one of said R1, R2, R3, R4 and R7 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from a group containing ##STR12## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R3, R4 and R7, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R1 and R2 ;
and when any one of said R3, R4, and R7 groups is not selected from one said reactive moiety, said remaining R3, R4, and R7 are hydrogen or E-F, a polar group wherein E is a spacer group having the structure --(CH2)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 R1 and R2 groups is not selected from one said reactive moiety, said remaining R1 or R2 are a lower alkyl or said E-F and n of said spacer group=1, 2, 3, or 4;
at least one said R8 and R9 groups is selected from the group consisting of a sulfonic acid and sulfonate moiety attached directly to one of said one ring to three fused rings, for conferring luminescence to said dye, wherein said ring or rings to which said sulfonic acid or sulfonate moiety is attached is an aryl ring; and
when one of said R8 or R9 group is not said sulfonic acid or sulfonate moiety, said remaining R8 or R9 group is a hydrogen.
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Abstract
A method for detecting a component of an aqueous liquid comprising adding to the liquid a luminescent dye selected from the group consisting of cyanine, merocyanine and styryl dyes containing at least one sulfonic acid or sulfonate group attached to an aromatic nucleus and reacting the dye with the component. The labeled component is then detected by an optical detection method.
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Citations
9 Claims
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1. A water soluble luminescent dye ponsisting of:
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a cyanine having the structure ##STR11## 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 R3, R4, R8 and R9 groups are attached to said rings;X and Y are S; m is an integer selected from the grouping consisting of 1, 2 and 3; at least one of said R1, R2, R3, R4 and R7 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from a group containing ##STR12## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R3, R4 and R7, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R1 and R2 ; and when any one of said R3, R4, and R7 groups is not selected from one said reactive moiety, said remaining R3, R4, and R7 are hydrogen or E-F, a polar group wherein E is a spacer group having the structure --(CH2)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 R1 and R2 groups is not selected from one said reactive moiety, said remaining R1 or R2 are a lower alkyl or said E-F and n of said spacer group=1, 2, 3, or 4; at least one said R8 and R9 groups is selected from the group consisting of a sulfonic acid and sulfonate moiety attached directly to one of said one ring to three fused rings, for conferring luminescence to said dye, wherein said ring or rings to which said sulfonic acid or sulfonate moiety is attached is an aryl ring; and when one of said R8 or R9 group is not said sulfonic acid or sulfonate moiety, said remaining R8 or R9 group is a hydrogen. - View Dependent Claims (2, 3, 4, 5)
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6. A water soluble luminescent dye consisting of a cyanine having the structure ##STR15## wherein:
- X and Y are S;
m is an integer selected from the group consisting of 1, 2 and 3; at least one of said R1, R2, R3, R4, R7, R10 and R11 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from the group consisting of;
##STR16## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R3, R4, R7, R10 and R11, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R1 and R2 ;and when any one of said R3, R4, and R7 groups is not selected from one said reactive moiety, said remaining R3, R4, and R7 are hydrogen or E-F, a polar group wherein E is a spacer group having the structure --(CH2)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 R1 and R2 groups, is not selected from one said reactive group, said remaining R1 and R2 are lower alkyl or said E-F and n=1, 2, 3, or 4; said R8 and R9, and said R10 and R11 groups when said R10 and R11 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 R8, R9, R10 and R11 groups is one of said sulfonic acid or sulfonate moiety attached directly to an aryl ring or rings of said structure for conferring luminescence to said dye.
- X and Y are S;
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7. A water soluble luminescent dye consisting of:
- ##STR17## wherein X and Y are S;
m is an integer selected from the group consisting of 1, 2 and 3; at least one of said R1 and R2 is ##STR18## and the other is selected from the group consisting of ##STR19## --CH2 CH2 OH, --(CH2)k SO3 where n=1, 2, 3, 4, 5, 6, 7 or 8 and k=2, 3, 4 or 5; and at least one of said R8 and R9 groups is a sulfonic acid or sulfonate moiety attached directly to an aryl ring of said dye for conferring luminescence to said dye; and when one of said R8 and R9 group is not said sulfonic acid or sulfonate moiety, said remaining R8 or R9 group is a hydrogen.
- ##STR17## wherein X and Y are S;
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8. A water soluble luminescent dye consisting of:
- ##STR20## wherein X and Y are S;
m is an integer selected from the group consisting of 1, 2 and 3; at least one of said R1 and R2 is ##STR21## and the other is selected from the group consisting of ##STR22## --CH2 CH2 OH, --(CH2)k SO3 where n=1, 2, 3, 4, 5, 6, 7, or and k=2, 3, 4, or 5; at least two of said R8, R9, R10 and R11 groups are a sulfonic acid or sulfonate moiety attached directly to an aryl ring of said dye for conferring luminescence to said dye; and when any one of said R8, R9, R10 and R11 groups is not said sulfonic acid or sulfonate moiety, it is a hydrogen.
- ##STR20## wherein X and Y are S;
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9. A water soluble luminescent dye consisting of:
- ##STR23## wherein X and Y are S;
m is an integer selected from the group consisting of 1, 2, and 3; at least one of said R1 and R2 is ##STR24## and the other is selected from the group consisting of ##STR25## --CH2 CH2 OH, --(CH2)k SO3 where n=1, 2, 3, 4, 5, 6, 7 or 8 and k=2, 3, 4 or 5; at least two of said R8, R9 and R10 groups comprise a sulfonic acid or sulfonate moiety attached directly to an aryl ring of said dye for conferring luminescence to said dye; and when any one of said R8, R9 or R10 is not said sulfonic acid or sulfonate moiety, it is a hydrogen.
- ##STR23## wherein X and Y are S;
Specification