Cell permeable ATP analog for kinase-catalyzed biotinylation
A cell permeable ATP analog has the following formula: or a physiologically acceptable salt thereof, wherein: R 0 is n, o, p are each independently 1, 2, 3, 4, 5, or 6, m is 0, 1, 2, 3, 4, or 5; X is O, S, NH, or CH 2 . R 1 is H or C 1-6 alkyl, R 2 is H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl; R 3 , R 4 are each independently H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl, wherein R 3 , and R 4 can be combined together to form a ring structure.
1. A cell permeable ATP analog having the following formula:
or a physiologically or pharmaceutically acceptable salt thereof, wherein:
n, o, p are each independently 1, 2, 3, 4, 5, or 6;
m is 0, 1, 2, 3, 4, or 5;
X is O, S, NH, or CH 2 ;
R 1 is H or C 1-6 alkyl,
R 2 is H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl; and
R 3 , R 4 are each independently H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl, wherein R 3 , and R 4 can be combined together to form a ring structure.
2. The cell permeable ATP analog of claim 1 wherein R 1 is H, methyl, ethyl, isopropyl or propyl and R 2 , R 3 , R 4 are each independently H.
3. The cell permeable ATP analog of claim 1 wherein R 1 is H or methyl and R 2 , R 3 , R 4 are each independently H.
4. The cell permeable ATP analog of claim 1 wherein is methyl, ethyl, propyl,
5. The cell permeable ATP analog of claim 1 wherein R 3 , R 4 are each independently H, methyl, ethyl, propyl,
6. The cell permeable ATP analog of claim 1 having the following formula:
7. The cell permeable ATP analog of claim 1 having the following formula:
8. The cell permeable ATP analog of claim 1 wherein n is 3, o is 4, p is 3, and m is 1.
9. The cell permeable ATP analog of claim 1 wherein the cell permeable ATP analog and chitosan combine to form a particle.
10. The cell permeable ATP analog of claim 1 wherein the cell permeable ATP analog and deacetylated chitosan combine to form a particle.
11. The cell permeable ATP analog of claim 10 wherein the particle has a size from 100 to 1000 nm.
12. A compound having the following formula:
or a physiologically or pharmaceutically acceptable salt thereof, wherein:
n, o, p are each independently 1, 2, 3, 4, 5, or 6;
m is 0, 1, 2, 3, 4, or 5;
X is O, S, NH, or CH 2 ;
R 1 is H or C 1-6 alkyl,
R 2 is H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl; and
R 3 , R 4 are each independently H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl, wherein R 3 , and R 4 can be combined together to form a ring structure.
13. A cell permeable ATP analog having the following formula:
or a physiologically or pharmaceutically acceptable salt thereof, wherein:
R 1 is H or C 1-6 alkyl,
R 2 is H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl;
R 3 , R 4 are each independently H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl, wherein R 3 , and R 4 can be combined together to form a ring structure.
14. The cell permeable ATP analog of claim 13 wherein R 1 is H, methyl, ethyl, or propyl and R 2 , R 3 , R 4 are each independently H.
15. The cell permeable ATP analog of claim 13 wherein R 1 is H or methyl and R 2 , R 3 , R 4 are each independently H.
16. The cell permeable ATP analog of claim 13 wherein is methyl, ethyl, or propyl,
17. The cell permeable ATP analog of claim 13 wherein R 3 , R 4 are each independently H, methyl, ethyl, propyl,
18. The cell permeable ATP analog of claim 13 wherein the cell permeable ATP analog and chitosan combine to form a particle.
19. The cell permeable ATP analog of claim 13 wherein the cell permeable ATP analog and deacelylated chitosan combine to form a particle.
20. A method for introducing cell permeable ATP analog into a cell from a subject, the method comprising:
a) contacting a cell with a cell permeable ATP analog having the following formula:
or a physiologically or pharmaceutically acceptable salt thereof, wherein:
n, o, p are each independently 1, 2, 3, 4, 5, or 6;
m is 0, 1, 2, 3, 4, or 5;
X is O, S, NH, or CH 2 ;
R 1 is H or C 1-6 alkyl,
R 2 is H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl;
R 3 , R 4 are each independently H, C 1-6 alkyl, C 6-30 aryl, C 5-32 heteroaryl, or C 7-32 alkylaryl, wherein R 3 , and R 4 can be combined together to form a ring structure.
21. The method of claim 20 further comprising:
b) determining if the cell permeable ATP analog has entered the cell with a portion of the cell permeable ATP analog having attached a protein substrate.
22. The method of claim 20 wherein the cell permeable ATP analog further comprises chitosan.
23. The method of claim 20 wherein the cell permeable ATP analog further comprises deacetylated chitosan.