Isatoic anhydride derivatives and applications thereof

Abstract

Isatoic anhydride derivatives having an N-substituent which includes a quaternary ammonium group are useful for labeling and/or functionalizing a target material and/or for coupling materials together. The isatoic anhydride derivatives of the present disclosure can be advantageously water soluble, easily prepared and purified. Isatoic anhydride derivatives useful in the present disclosure preferably have at least one chemically reactive group or at least one binding group or at least one detectable label. Anthranilate derivatives made from the isatoic anhydrides derivatives or otherwise and kits including the isatoic anhydride derivatives are also disclosed.

1 - 6 . (canceled) 
     
     
         7 . An anthranilate derivative according to Formula (III): 
       
         
           
           
               
               
           
         
         wherein V, W, Y, and Z individually represent H, N 3 , NO 2 , amino, alkylamino, dialkylamino, branched or linear alkyl, branched or linear alkenyl, branched or linear alkynyl, branched or linear alkoxy, branched or linear sulfenyl, an alkyne or azido substituted alkylamino, dialkylamino, alkyl, alkoxy, sulfenyl, formyl, acetyl, or halide; L 1  represents a linker group; R 3  and R 4  independently represent a linear or branched alkyl, an alkyl ether, or together form a cyclic heteroalkyl, or cyclic heteroaryl; Q −  represents an anion; p is an integer from 0 to 2; when p is 0, L 2  represents a pendant organo group; when p greater than 0, L 2  represents a second independent linker group; R 1  represents a chemically reactive group, a binding group, or a detectable label; M represents a material; and Xa represents NH, NR 5 , S, or O. 
       
     
     
         8 . The anthranilate derivative of  claim 7 , wherein M represents a biological material. 
     
     
         9 . The anthranilate derivative of  claim 7 , wherein M represents a formula -L 3 -R″ 1 ; wherein L 3  represents a linker group; and R″ 1  represents a chemically reactive group, a binding group, or a detectable label. 
     
     
         10 . A kit comprising at least a first isatoic anhydride derivative having an N-substituent which includes a quaternary ammonium group and wherein the isatoic anhydride derivative has at least one chemically reactive group or at least one binding group. 
     
     
         11 . The kit according to  claim 10 , further comprising a second isatoic anhydride derivative having an N-substituent which includes a quaternary ammonium group, wherein the first isatoic anhydride derivative includes a first chemically reactive group, and the second isatoic anhydride derivative includes a second chemically reactive group that can chemically react with the first chemically reactive group of the first isatoic anhydride derivative to couple the first and second isatoic anhydride derivatives. 
     
     
         12 . A multiplex isatoic anhydride having one or more deuterium atoms substituted for one or more hydrogen atoms, having formula (V): 
       
         
           
           
               
               
           
         
         wherein V, W, Y, and Z individually represent H, N 3 , NO 2 , amino, alkylamino, dialkylamino, branched or linear alkyl, branched or linear alkenyl, branched or linear alkynyl, branched or linear alkoxy, branched or linear sulfenyl, an alkyne or azido substituted alkylamino, dialkylamino, alkyl, alkoxy, sulfenyl, formyl, acetyl, or halide; and R represents an organo substituent having one or more hydrogen atoms substituted by one or more deuterium atoms.