Functionalized linear ligands and complexes thereof
AssigneeLumiphore, Inc.
InventorsNathaniel G. BUTLIN, Darren MAGDA, Jide XU
Life of this patent
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Abstract
The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.
Claims37
A compound having a structure selected from:
- wherein
- Y1 and Y2 are independently selected from H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl;
- Bs1, Bs2, Bs3, Bs4, Bs5, and Bs6 are independently selected from N, CRs, B, SiRs, and P;
- wherein Rs is selected from H and unsubstituted C1-C3 alkyl;
- LA1, LA2, LA3, LA4, LA5, and LA6 are independently selected from a bond, —C(O)—, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl;
- Ls1, Ls2, Ls3, Ls4, and Ls5 are independently selected from substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl;
- and
- A1, A2, A3, A4, A5, and A6 are chelating moieties having a structure independently selected from
- wherein
- A and G are independently selected from carbon, nitrogen and oxygen;
- J is selected from carbon and nitrogen;
- each R1 and R2 are independently selected from H, an enzymatically labile group, a hydrolytically labile group, a metabolically labile group, a photolytically labile group and a single negative charge;
- each R6, R7, R8, R9, and R10 are independently selected from a bond to LA1, LA2, LA3, LA4, LA5, or LA6, alkanediyl attached to LA1, LA2, LA3, LA4, LA5, or LA6, H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, halogen, CN, —CF3, —C(O)R17, —SO2NR17R18, —NR17R18, —OR17, —S(O)2R17, —COOR17, —S(O)2OR17, —OC(O)R17, —C(O)NR17R18, —(CH2)mC(O)NR17R18, —O(CH2)mC(O)NR17R18, NR17C(O)R18, NR17SO2R18, and —NO2,
- wherein
- at least two of R6, R7, R8, R9, and R10 are optionally joined to form a ring system selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- m is an integer selected from 1, 2, 3, 4, 5, and 6;
- R17 and R18 are independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl;
- and
- R17 and R18, together with the atoms to which they are attached, are optionally joined to form a 5-, 6- or 7-membered ring;
- when A is oxygen, R9 is not present;
- and
- when G is oxygen, R7 is not present;
- A1 is attached to LA1 through a member selected from R6, R7, R8, R9 and R10;
- A2 is attached to LA2 through a member selected from R6, R7, R8, R9 and R10;
- A3 is attached to LA3 through a member selected from R6, R7, R8, R9 and R10;
- A4 is attached to LA4 through a member selected from R6, R7, R8, R9 and R10;
- A5 is attached to LA5 through a member selected from R6, R7, R8, R9 and R10;
- and
- A6 is attached to LA6 through a member selected from R6, R7, R8, R9 and R10;
- wherein said compound comprises a linker.
The compound according to any one of the preceeding claims, wherein A1, A2, A3, A4, A5, and A6 are each independently selected from:
The compound according to any one of the preceeding claims, wherein Ls1, Ls2, Ls3, Ls4, and Ls5 are each independently selected from substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7 and C8 alkyl.
The compound according to any one of the preceeding claims, wherein at least one of Ls1, Ls2, Ls3, Ls4, and Ls5 is substituted with a linker.
The compound according to any one of the preceeding claims, wherein Bs1, Bs2, Bs3, Bs4, Bs5, and Bs6 are each N.
The compound according to any one of the preceeding claims, wherein LA1, LA2, LA3, LA4, LA5, and LA6 are independently selected from a bond, —C(O)—, —(CH2)aC(O)—, and —O(CH2)aC(O)—;
- wherein a is an integer selected from 1, 2, 3, 4, 5, and 6.
The compound according to any one of the preceeding claims, wherein LA1, LA2, LA3, LA4, LA5, and LA6 are the same.
The compound according to any one of the preceeding claims, wherein LA1, LA2, LA3, LA4, LA5, and LA6 are each —C(O)—.
The compound according to any one of the preceeding claims, wherein Y1 and Y2 are each H.
The compound according to any one of the preceeding claims, having the structure
- wherein
- Ls1 and Ls3 are each independently selected from substituted or unsubstituted C2, C3, and C4 alkyl;
- and
- Ls2 is selected from substituted or unsubstituted C3, C4, and C5 alkyl;
- wherein at least one of Ls1, Ls2, and Ls3 is substituted with said linker.
The compound according to any one of the preceeding claims, having the structure
- wherein Lx1 is said linker.
The compound according to any one of the preceeding claims, wherein said linker has the structure −L11−X,
- wherein L11 is selected from a bond, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- and
- X is selected from a reactive functional group, a protected functional group, and a targeting moiety.
The compound according to any one of the preceeding claims, wherein said linker has the structure:
- wherein RL is seleceted from substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl;
- and X is selected from a reactive functional group, a protected functional group, and a targeting moiety.
The compound according to any one of the preceeding claims, wherein said linker has a structure selected from:
The compound according to any one of the preceeding claims, wherein said compound comprises one or more modifying moiety.
A complex comprising a compound according to any one of the preceding claims and a metal ion.
Dependencies are inferred from the claim text.