Fluorescent polymethine cyanine dyes

Abstract

The invention encompasses fluorescent cyanine dyes and methods of using such dyes. In particular, the invention encompasses near infrared polymethine cyanine dyes.

What is claimed is: 
     
         1 . A fluorescent cyanine dye, the dye having two nitrogen atoms that are each independently a part of at least two different heteroaromatic rings, the heteroaromatic rings being joined by a polymethine chain, the polymethine chain comprising a carbocylic ring that is centrally located within the polymethine chain, the carbocylic ring being derivatized with a hydrocarbyl or a substituted hydrocarbyl group at the meso position in a manner such that the dye is substantially fluorescent. 
     
     
         2 . The fluorescent cyanine dye of  claim 1 , wherein the absorption maxima is at least 600 nm. 
     
     
         3 . The fluorescent cyanine dye of  claim 1 , wherein the dye comprises Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein:
 A is a cyclic group selected from a carbocyclic ring, and a heterocyclic ring; 
 X and Y are independently selected from the group consisting of a heteroatom, an alkyl group, an alkenyl group, and an alkynyl group; 
 n and m are independent integers from 1 to about 5; 
 R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  and R 11  are independently selected from the group consisting of functional group, hydrogen, hydrocarbyl, and substituted hydrocarbyl; and 
 R 3  and R 12  are selected from the group consisting of hydrocarbyl, and substituted hydrocarbyl. 
 
     
     
         4 . The fluorescent cyanine dye of  claim 1 , wherein the dye comprises Formula (II): 
       
         
           
           
               
               
           
         
       
       wherein:
 X is selected from the group consisting of a heteroatom, an alkyl group, an alkenyl group, and an alkynyl group; 
 R 1 , R 2 , and R 4  are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl; and 
 R 3  and R 5  are selected from the group consisting of hydrocarbyl, substituted hydrocarbyl. 
 
     
     
         5 . The fluorescent cyanine dye of  claim 1 , wherein the dye comprises Formula (III): 
       
         
           
           
               
               
           
         
       
       wherein:
 n is an integer from 1 to 10; 
 R 1 , and R 2 , and R 4  are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl; and 
 R 5  is selected from the group consisting of hydrocarbyl, and substituted hydrocarbyl. 
 
     
     
         6 . A compound, the compound comprising the fluorescent cyanine dye of  claim 1  conjugated to a biomolecule. 
     
     
         7 . The compound of  claim 6 , wherein the biomolecule is selected from the group consisting of an antigen, an antibody, a drug, a vitamin, and a small molecule. 
     
     
         8 . The compound of  claim 6 , wherein the biomolecule is selected from the group consisting of a peptide, a nucleic acid, a carbohydrate, and a lipid. 
     
     
         9 . The compound of  claim 8 , wherein the biomolecule is a peptide.