IP Library Granted Patent US 8,716,344
Granted Patent B2
US 8,716,344 · App. 13/389,814 · Granted May 6, 2014

Class- and isoform-specific HDAC inhibitors and uses thereof

Inventors: Ralph Mazitschek (Belmont, MA); James Elliot Bradner (Cambridge, MA)
Assignees: President and Fellows of Harvard College; Dana-Farber Cancer Institute, Inc.
A61K38/05A61K45/06A61K31/495C07D239/42C07D401/04C12Q1/48
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Quick Facts
Patent No.
US 8,716,344
App. No.
13/389,814
Granted
May 6, 2014
Kind
B2
Abstract

The present invention relates to compounds of the following formula wherein R 3 is a fluorescent tag. Another aspect of the invention provides an assay for determining the inhibitory effect of a test compound on an HDAC protein comprising: incubating the HDAC protein with a substrate of the above formula in the presence of a test compound; and determining the activity of the HDAC protein.

Claims (24)

1. A compound of formula:

wherein R 3 is a fluorescent tag;

or salt thereof.

2. The compound of claim 1 , wherein R 3 comprises coumarin.

3. The compound of claim 1 , wherein the compound is:

4. The compound of claim 1 , wherein the fluorescent tag of R 3 can be cleaved by an enzyme.

5. An assay for determining the inhibitory effect of a test compound on an HDAC protein comprising: incubating the HDAC protein with a substrate of claim 1 in the presence of a test compound; and determining the activity of the HDAC protein.

6. An assay for determining the inhibitory effect of a test compound on an HDAC protein comprising incubating the HDAC protein with a substrate of formula:

in the presence of a test compound; and determining the activity of the HDAC protein by monitoring the release of 7-amino-4-methylcoumarin after cleavage by trypsin.

7. The compound of claim 1 , wherein the fluorescent tag is selected from a group consisting of brodifacoum, bromadiolone, coumafuryl, difenacoum, auraptene, ensaculin, phenprocoumon, warfarin, and derivatives thereof.

8. The compound of claim 4 , wherein the enzyme is esterase.

9. The compound of claim 4 , wherein the enzyme is protease.

10. The compound of claim 4 , wherein the enzyme is serine protease.

11. The compound of claim 4 , wherein the enzyme is trypsin.

12. The compound of claim 1 , wherein the fluorescent tag of R 3 can be removed by a mechanical process.

13. The compound of claim 1 , wherein R 3 comprises a coumarin derivative thereof.

14. The assay of claim 5 , wherein the step of determining the activity of the HDAC protein comprises monitoring the release of the fluorescent tag from the substrate.

15. The assay of claim 5 , wherein the fluorescent tag comprises coumarin or a derivative thereof.

16. The assay of claim 5 , wherein the assay is carried out at a concentration of the substrate greater than the substrate K m .

17. The assay of claim 5 , wherein the assay is carried out at a concentration of the substrate approximately equivalent to the substrate K m .

18. The assay of claim 5 , wherein the concentration of the substrate is 1-20 μM.

19. The assay of claim 5 , wherein the HDAC protein is a Class II HDAC.

20. The assay of claim 5 , wherein the HDAC protein is 0.01-5 ng/μL.

21. The assay of claim 5 , wherein the HDAC protein is 0.1-0.5 ng/μL.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2012
From: MAZITSCHEK, RALPH
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 028681/0278 →
CONFIRMATORY LICENSE Recorded Mar 6, 2012
From: HARVARD UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 027810/0029 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2012
From: BRADNER, JAMES ELLIOT
To: DANA-FARBER CANCER INSTITUTE, INC.
Reel/Frame 027795/0049 →
Continuity (2)
Provisional Application 61233035 · Aug 11, 2009
Related Publication 20120208889A1 · Aug 16, 2012