Environmentally sensitive fluorophores
The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment-sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.
1. An article, comprising:
a compound of formula (I):
wherein R 6 and R 7 are independently hydrogen, halogen, alkyl, or —NR 1 R 2 such that at least one of R 6 and R 7 is —NR 1 R 2 , R 1 and R 2 each independently being a substituted or unsubstituted alkyl;
Y is a, —SH, —NHR 3 , —C(O)X 1 , -maleimidyl, —NHCOR 3 , —NHCO(CH 2 )X 2 , or —CH(NHR 3 )COOH;
R 3 is hydrogen, substituted or unsubstituted alkyl, or an N-protecting group;
X 1 is hydrogen, halogen, hydroxy, alkoxy, or O-succidimidyl;
X 2 is hydrogen, halogen, hydroxy, alkoxy; and
n is 0, 1, 2, or 3.
2. The article of claim 1 , wherein the compound has a formula (II):
3. The article of claim 1 , wherein R 6 is —NR 1 R 2 and R 7 is —H.
4. The article of claim 2 , wherein the compound has a formula (V):
5. The article of claim 2 , wherein the compound has a formula (VI):
6. The article of claim 5 , wherein R 3 is H.
7. The article of claim 1 , wherein the compound has a formula (VII):
wherein Z is —SH, —NHR 3 , —C(O)X 1 , -maleimidyl, —NHCOR 3 , or —NHCO(CH 2 )X 2 .
8. The article of claim 7 , wherein Z is —SH or —NH 2 .
9. The article of claim 7 , wherein the compound has a formula (VIII):
10. The article of claim 9 , wherein the compound has a formula (IX):
11. The article of claim 10 , wherein n is 0.
12. The article of claim 10 , wherein n is 1.
13. The article of claim 10 , wherein n is 2.
14. The article of claim 7 , wherein the compound has a formula (X):
wherein Z 1 is halogen.
15. The article of claim 14 , wherein the compound has a formula (XI):
16. The article of claim 15 , wherein n is 0.
17. The article of claim 15 , wherein n is 1.
18. The article of claim 15 , wherein n is 2.
19. The article of claim 15 , wherein Z 1 is I.
20. The article of claim 15 , wherein Z 1 is Br.
21. The article of claim 15 , wherein Z 1 is Cl.
22. The article of claim 7 , wherein the compound has a formula (XII):
23. The article of claim 1 , wherein the article is a sensor.
24. An article, comprising:
a compound of formula (XIX):
wherein R 6 and R 7 are independently hydrogen, halogen, alkyl, or —NR 1 R 2 such that at least one of R 6 and R 7 is —NR 1 R 2 , R 1 and R 2 each independently being a substituted or unsubstituted alkyl;
Y is a halogen, —SH, —NHR 3 , —C(O)X 1 , -maleimidyl, —NHCOR 3 , —NHCO(CH 2 )X 2 , or —CH(NHR 3 )COOH;
R 3 is hydrogen, substituted or unsubstituted alkyl, or an N-protecting group;
X 1 is hydrogen, halogen, hydroxy, alkoxy, or O-succidimidyl;
X 2 is hydrogen, halogen, hydroxy, alkoxy; and
n is 0, 1, 2, or 3.
25. The article of claim 24 , wherein Y is a halogen.
26. The article of claim 24 , wherein Y is Br.
27. An article, comprising:
a compound of formula (XX):
wherein R 6 and R 7 are independently hydrogen, halogen, alkyl, or —NR 1 R 2 such that at least one of R 6 and R 7 is —NR 1 R 2 , R 1 and R 2 each independently being a substituted or unsubstituted alkyl.