IP Library Granted Patent US 9,096,844
Granted Patent B2
US 9,096,844 · App. 14/083,938 · Granted Aug 4, 2015

Photocleavable linker

Inventors: John C. Williams (Duarte, CA); David Horne (Duarte, CA); Jun Xie (Duarte, CA); Shubbir Ahmed (Duarte, CA)
Assignee: City of Hope
C12N9/96C12N9/90C12N9/93C12Y502/01008
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Quick Facts
Patent No.
US 9,096,844
App. No.
14/083,938
Granted
Aug 4, 2015
Kind
B2
Abstract

There are provided, inter alia, photolabile compounds and methods useful for the formation of dimers of biological molecules and subsequent dissociation of the dimers.

Claims (33)

1. A compound having the formula:

wherein,

L 1 is a photocleavable linker, and z 1 and z 2 are each independently an integer in the range 0 to 6.

2. The compound of claim 1 , wherein

L 1 is substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted heterocycloalkylene, substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene.

3. The compound of claim 1 , wherein L 1 comprises a nitrophenylene.

4. The compound of claim 1 , wherein L 1 has the formula:

-L 2 -L 3 -L 4 -L 5 -L 6 -

wherein

L 2 and L 6 are —C(O)O;

L 3 and L 5 are independently a bond or substituted or unsubstituted alkylene;

L 4 is R 1 -substituted arylene; and

R 1 is an electron withdrawing group.

5. The compound of claim 4 , wherein

R 1 is halogen, —NO 2 , N + (R 2 ) 3 , —SR 2 , —OR 2 , —N(R 2 ) 2 , —CF 3 , —CCl 3 , —CN, —SO 3 R 2 , —COOR 2 , —CHO or —COR 2 ; and

R 2 is hydrogen or an unsubstituted C 1 to C 4 alkyl.

6. The compound of claim 4 , wherein L 1 is:

7. The compound of claim 4 , wherein L 3 and L 5 are independently substituted or unsubstituted alkylene.

8. The compound of claim 4 , wherein L 3 and L 5 are independently substituted or unsubstituted C 1 to C 4 alkylene.

9. The compound of claim 4 , wherein L 3 and L 5 are independently substituted or unsubstituted C 1 to C 3 alkylene.

10. The compound of claim 4 , wherein L 3 and L 5 are substituted with an unsubstituted C 1 to C 4 alkylene.

11. The compound of claim 4 , wherein L 3 and L 5 are substituted with a methyl.

12. The compound of claim 4 , wherein L 3 and L 5 are methylene substituted with an unsubstituted C 1 to C 4 alkylene.

13. The compound of claim 4 , wherein L 1 is:

14. The compound of claim 4 , wherein R 1 is NO 2 .

15. The compound of claim 1 having the formula:

16. The compound of claim 1 having the formula:

17. The compound of claim 1 having the formula:

18. A method of forming an FK506 binding protein (FKBP) dimer, the method comprising:

(i) contacting a first FKBP and a second FKBP with the compound of claim 1 ; and

(ii) allowing said compound to bind to said first FKBP and said second FKBP thereby forming an FKBP dimer comprising a link between said first FKBP and said second FKBP.

19. The method of claim 18 , further comprising:

(iii) exposing said FKBP dimer to a photon thereby cleaving said link.

Assignments (2)
CONFIRMATORY LICENSE Recorded Nov 3, 2015
From: CITY OF HOPE/BECKMAN RESEARCH INSTITUTE
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 037035/0266 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2015
From: WILLIAMS, JOHN C.; HORNE, DAVID; XIE, JUN; AHMED, SHUBBIR
To: CITY OF HOPE
Reel/Frame 035252/0070 →
Continuity (2)
Provisional Application 61728138 · Nov 19, 2012
Related Publication 20140154775A1 · Jun 5, 2014