IP Library Granted Patent US 9,267,137
Granted Patent B2
US 9,267,137 · App. 14/597,676 · Granted Feb 23, 2016

MicroRNA compounds and methods for modulating miR-21 activity

Inventors: Balkrishen Bhat (San Diego, CA); Eric Marcusson (San Francisco, CA)
Assignee: Regulus Therapeutics Inc.
C12N15/113A61K31/712A61K45/06C12N15/1135C12N2310/11C12N2310/113C12N2310/3341C12N2310/343C12N2310/346
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,267,137
App. No.
14/597,676
Granted
Feb 23, 2016
Kind
B2
Abstract

Described herein are compositions and methods for the inhibition of miR-21 activity. The compositions have certain nucleoside modification patterns that yield potent inhibitors of miR-21 activity. The compositions may be used to inhibit miR-21, and also to treat diseases associated with abnormal expression of miR-21, such as fibrosis and cancer.

Claims (32)

1. A compound comprising a modified oligonucleotide consisting of 12, 13, 14, or 15 linked nucleosides, wherein the nucleobase sequence of the modified oligonucleotide is complementary to miR-21 (SEQ ID NO: 1) and wherein the modified oligonucleotide comprises at least 12 contiguous nucleosides of the following nucleoside pattern VI in the 5′ to 3′ orientation:

N Q —N B —N B —N Q —(N B —N B —N Q —N Q ) 2 —N B —N Q —N B

wherein each N Q is a non-bicyclic nucleoside; and

each N B is a bicyclic nucleoside.

2. The compound of claim 1 , wherein each bicyclic nucleoside is independently selected from an LNA nucleoside, a cEt nucleoside, and an ENA nucleoside.

3. The compound of claim 1 , wherein each non-bicyclic nucleoside is independently selected from a β-D-deoxyribonucleoside, a 2′-O-methyl, and a 2′-O-methoxyethyl nucleoside.

4. The compound of claim 1 , wherein each non-bicyclic nucleoside is independently selected from a β-D-deoxyribonucleoside and a 2′-O-methoxyethyl nucleoside.

5. The compound of claim 1 wherein:

a. each N B is an S-cEt nucleoside; and

each N Q is a 2′-O-methoxyethyl nucleoside; or

b. each N B is an S-cEt nucleoside; and

each N Q is a β-D-deoxyribonucleoside.

6. The compound of claim 1 , wherein at least one internucleoside linkage is a phosphorothioate linkage.

7. The compound of claim 1 , wherein each internucleoside linkage is a phosphorothioate linkage.

8. The compound of claim 1 , wherein the modified oligonucleotide has 1 or 2 mismatches with respect to the nucleobase sequence of miR-21.

9. The compound of claim 1 , wherein the modified oligonucleotide has 0 mismatches with respect to the nucleobase sequence of miR-21.

10. The compound of claim 1 , wherein the modified oligonucleotide has a nucleobase Sequence of SEQ ID NO: 5 or 7, wherein each T is independently selected from T and U.

11. The compound of claim 1 , wherein the modified oligonucleotide has the structure:

Me C E A S A S T E C S U S A E A E U S A S A E G E C S T E A S (SEQ ID NO: 7);

wherein nucleosides followed by a subscript “E” are 2′-MOE nucleosides; nucleosides followed by a subscript “S” are S-cEt nucleosides; and superscript “Me” indicates a 5-methyl group on the base of the nucleoside.

12. The compound of claim 11 , wherein at least one internucleoside linkage is a phosphorothioate linkage.

13. The compound of claim 11 , wherein each internucleoside linkage is a phosphorothioate linkage.

14. A modified oligonucleotide of structure:

Me C E A S A S T E C S U S A E A E U S A S A E G E C S T E A S (SEQ ID NO: 7);

wherein nucleosides followed by a subscript “E” are 2′-MOE nucleosides; nucleosides followed by a subscript “S” are S-cEt nucleosides; superscript “Me” indicates a 5-methyl group on the base of the nucleoside; and wherein each internucleoside linkage of the modified oligonucleotide is a phosphorothioate linkage.

15. A pharmaceutical composition comprising the modified oligonucleotide of claim 14 and a pharmaceutically acceptable carrier.

16. The compound of claim 1 , wherein the modified oligonucleotide is conjugated to one or more moieties that enhance the activity, cellular distribution or cellular uptake.

17. The compound of claim 1 , wherein the modified oligonucleotide is conjugated to a moiety selected from a lipid, cholesterol, a carbohydrate, a phospholipid, biotin, phenazine, and folate.

18. The compound of claim 11 , wherein the modified oligonucleotide is conjugated to one or more moieties that enhance the activity, cellular distribution or cellular uptake.

19. The compound of claim 11 , wherein the modified oligonucleotide is conjugated to a moiety selected from a lipid, cholesterol, a carbohydrate, a phospholipid, biotin, phenazine, and folate.

20. A pharmaceutical composition comprising the modified oligonucleotide of claim 1 and a pharmaceutically acceptable carrier.

21. The compound of claim 1 , wherein the modified oligonucleotide consists of 15 contiguous nucleosides of nucleoside pattern VI.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded May 14, 2024
From: OXFORD FINANCE LLC, AS COLLATERAL AGENT AND LENDER
To: REGULUS THERAPEUTICS INC.
Reel/Frame 067402/0782 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2019
From: REGULUS THERAPEUTICS INC.
To: SANOFI
Reel/Frame 049344/0688 →
RELEASE OF SECURITY INTEREST Recorded Nov 7, 2018
From: OXFORD FINANCE LLC
To: REGULUS THERAPEUTICS INC.
Reel/Frame 047445/0286 →
SECURITY INTEREST Recorded Aug 8, 2018
From: REGULUS THERAPEUTICS INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT AND LENDER
Reel/Frame 046748/0561 →
Continuity (5)
Division 13869177 · Apr 24, 2013
Provisional Application 61741783 · Apr 25, 2012
Provisional Application 61717927 · Oct 24, 2012
Provisional Application 61779913 · Mar 13, 2013
Related Publication 20150218558A1 · Aug 6, 2015