Salicylamide-lanthanide complexes for use as luminescent markers

Abstract

The present invention provides luminescent lanthanide metal chelates comprising a metal ion of the lanthanide series and a complexing agent comprising at least one salicylamidyl moiety. Also provided are probes incorporating the salicylamidyl ligands of the invention and methods utilizing the ligands of the invention and probes comprising the ligands of the invention.

1 - 112 . (canceled) 
     
     
         113 . A luminescent complex formed between a lanthanide ion and a compound having a structure according to Formula I: 
       
         
           
           
               
               
           
         
         wherein,
 R 1  and R 2  are members independently selected from the group consisting of alkyl, substituted alkyl, polyether, substituted polyether, halogen and —OR 6 , wherein
 R 6  is a member selected from the group consisting of H, alkyl, substituted alkyl groups, polyether, substituted polyether, and a single negative charge; 
 
 R 4 , R 5 ; R 7 , R 10 , and R 20  are members independently selected from the group consisting of H, polyether, substituted polyether, alkyl and substituted alkyl groups, 
 R 3 , R 8  and R 9  are members independently selected from the group consisting of polyether, substituted polyether, alkyl and substituted alkyl groups; 
 R 11 , R 12 , R 13 , R 21 , R 22  and R 23  are members independently selected from alkyl, substituted alkyl, H, —NR 14 R 15 , —NO 2 , OR 16 , —COOR 17 ,
 wherein, R 14 . R 15 , R 16  and R 17  are members independently selected from the group consisting of H, alkyl and substituted alkyl, wherein R 12  can optionally from a ring with R 11 , R 13  or both, and R 22  can optionally form a ring with R 21 , R 23  or both, said rings being members independently selected from the group of ring systems consisting of cyclic alkyl, substituted cyclic alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl and substituted heterocyclyl ring systems; and 
 
 Q 1  is —OR 18 ; 
 Q 2  is —OR 19 ,
 wherein R 18  and R 19  are members independently selected from H, an enzymatically labile group, a hydrolytically labile group and a single negative charge; and 
 
 a and z are independently selected from the group consisting of 0 and 1, with the proviso that when a is 0, N 1  is covalently attached directly to carbonyl 1′, and when z is 0, N 2  is covalently attached directly to carbonyl group 2′.