Red-shifted luciferins and methods of using same
Novel red-shifted luciferin derivatives and uses of those compounds are provided.
1. A compound according to Formula (XI):
wherein
X is CN or
Y is OR; and
R is
2. A compound according to Formula (XII):
wherein
X is CN or
Y is OR;
R is
A is OH or NHAc; and
each R 5 is independently H, a monosaccharide or a polyethylene glycol moiety of up to 40 units.
3. A compound according to Formula (XIII):
wherein
X is CN or
Y is NHR;
R is
R 7 is an amino acid side chain; and
R 6 is H, a nitrogen protecting group, or a chain of up to 35 amino acids.
4. A compound according to Formula (XV):
wherein
X is CN or
Y is OR; and
R is C 1-10 alkyl, substituted C 1-10 alkylaryl, substituted aryl, aralkyl or substituted aralkyl.
5. A compound according to Formula (XVI):
wherein
X is —CH(OR 10 ) 2 ;
R 10 is C 1-4 alkyl, substituted C 1-4 alkyl, benzyl or substituted benzyl;
Y is OR 1 or NR 1 R 2 ; and
R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl;
R 2 is H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a 4 to 8 membered ring.
6. A compound according to Formula (XVII):
wherein
R 8 is CH 2 OH, C(O)R 10 or —C(O)ZR 9 ;
Z is O or NH;
R 9 is C 1-7 alkyl or substituted C 1-7 alkyl;
R 10 is a peptide;
Y is OR 1 or NR 1 R 2 ; and
R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl;
R 2 is H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a 4 to 8 membered ring.
7. A compound according to Formula (XVIII):
wherein
X is CN or
Y is OR;
R is
each R 11 is independently H, C 1-6 alkyl, substituted C 1-6 alkyl, CF 3 , halogen, NO 2 , or CO 2 R 12 provided that at least one of R 11 is NO 2 ;
R 12 is H, C 1-6 alkyl or substituted C 1-6 alkyl; and
m is 1 or 2.
8. A compound according to Formula (XX):
wherein
X is CN or
Y is L-R;
L is a linker; and
R is a boronic acid or borate ester.
9. A kit comprising a compound according to claim 1 .
10. The kit of claim 9 further comprising a luciferase.
11. The kit of claim 9 , further comprising a buffer reagent.
12. A compound according to Formula (XV):
wherein
X is
Y is H or OR; and
R is C 1-10 alkyl, substituted C 1-10 alkylaryl, substituted aryl, aralkyl or substituted aralkyl.