Red-shifted luciferins and methods of using same
View Patent ↗Novel red-shifted luciferin derivatives and uses of those compounds are provided.
1. A compound according to Formula (Ia):
wherein
X is CN or
each Y is independently halo, SO 3 H, C 1-4 alkyl, substituted C 1-4 alkyl, OR 1 or NR 1 R 2 ;
each R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl;
each 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; and
n is 1 to 6.
2. A compound according to claim 1 , wherein at least one Y is OH.
3. A compound according to claim 1 , wherein at least one Y is NR 1 R 2 .
4. A compound according to claim 1 , wherein at least one Y is OH or NR 1 R 2 and up to 5 additional Ys are halo groups.
5. A compound according to claim 4 , wherein the halo groups are fluoro.
6. A compound according to claim 4 , wherein the halo groups are chloro.
7. A compound according to claim 1 , wherein at least one Y is SO 3 H.
8. A compound according to claim 1 , wherein the compound is a compound of Formula (II):
wherein
X is CN or
Y is OR 1 or NR 1 R 2 ;
R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl; and
R 2 is H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a ring.
9. A compound according to claim 1 , wherein the compound is a compound of Formula (III):
wherein
X is CN or
Y is OR 1 or NR 1 R 2 ;
R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl; and
R 2 is H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a ring.
10. A compound according to claim 1 , wherein the compound is a compound of Formula (VII):
wherein
X is CN or
each Y is independently OR 1 or NR 1 R 2 ;
each R 1 is independently H, C 1-10 alkyl or substituted C 1-10 alkyl; and
each R 2 is independently H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a ring.
11. A compound according claim 1 , wherein X is CN.
12. A compound according to claim 1 , wherein X is
13. A compound according to claim 1 , wherein Y is NH 2 .
14. A method for detecting luminescence in a sample comprising
contacting a sample with a compound according to claim 1 ;
contacting the sample with a luciferase, if it is not present in the sample; and
detecting luminescence.
15. The method of claim 14 , wherein the sample contains live cells.
16. The method of claim 14 , wherein the sample contains a luciferase.
17. A method for detecting luminescence in a transgenic animal comprising
administering a compound according to claim 1 to a transgenic animal; and
detecting luminescence;
wherein the transgenic animal expresses a luciferase.
18. A kit comprising a compound according to claim 1 .
19. The kit of claim 18 further comprising a luciferase.
20. The kit of claim 18 further comprising a buffer reagent.
21. A compound selected from the group consisting of:
22. A compound according to claim 1 , wherein the compound is a compound of Formula (VI):
wherein
X is CN or
Y is OR 1 or NR 1 R 2 ;
R 1 is H, C 1-10 alkyl or substituted C 1-10 alkyl; and
R 2 is H, C 1-10 alkyl or substituted C 1-10 alkyl; or
R 1 and R 2 together form a ring.