IP Library Granted Patent US 8,969,317
Granted Patent B2
US 8,969,317 · App. 13/869,177 · Granted Mar 3, 2015

MicroRNA compounds and methods for modulating miR-21 activity

Inventors: Balkrishen Bhat (San Diego, CA); Eric Marcusson (San Francisco, CA)
Assignee: Regulus Therapeutics Inc.
C12N15/1135A61K31/712A61K45/06C12N2310/113C12N2310/3341C12N2310/343C12N2310/346
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Quick Facts
Patent No.
US 8,969,317
App. No.
13/869,177
Granted
Mar 3, 2015
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 (26)

1. A compound comprising a modified oligonucleotide consisting of 15, 16, 17, 18, or 19 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 15 contiguous nucleosides of the following nucleoside pattern VII in the 5′ to 3′ orientation:

N M -(N B -N M -N M ) 2 -N M -(N B -N Q -N Q -N Q ) 2 -N B -N B -N Z

wherein each N M is a 2′-O-methoxyethyl nucleoside;

each N B is an S-cEt nucleoside;

each N Q is a β-D-deoxyribonucleoside; and

N Z is an S-cEt nucleoside.

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

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

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

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

6. The compound of claim 1 , wherein modified oligonucleotide has a nucleobase sequence selected from SEQ ID NOs: 3, 5, 6, 7, 8, 9, and 10, wherein each T is independently selected from T and U.

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

A E C S A E T E C S A E G E T E C S TGAU S AAGC S U S A S ,

(SEQ ID NO: 3)

wherein nucleosides not followed by a subscript are β-D-deoxyribonucleosides; nucleosides followed by a subscript “E” are 2′-MOE nucleosides; and nucleosides followed by a subscript “S” are S-cEt nucleosides.

8. The compound of claim 7 , wherein at least one internucleoside linkage is a phosphorothioate linkage.

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

10. A compound comprising a modified oligonucleotide having the structure:

A E C S A E T E C S A E G E T E C S TGAU S AAGC S U S A S ,

(SEQ ID NO: 3)

wherein nucleosides not followed by a subscript are β-D-deoxyribonucleosides; nucleosides followed by a subscript “E” are 2′-MOE nucleosides; and nucleosides followed by a subscript “S” are S-cEt nucleosides; and wherein each internucleoside linkage of the modified oligonucleotide is a phosphorothioate linkage.

11. 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.

12. 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.

13. The compound of claim 10 , wherein the modified oligonucleotide is conjugated to one or more moieties that enhance the activity, cellular distribution or cellular uptake.

14. The compound of claim 10 , wherein the modified oligonucleotide is conjugated to a moiety selected from a lipid, cholesterol, a carbohydrate, a phospholipid, biotin, phenazine, and folate.

15. A pharmaceutical composition comprising the compound of claim 10 and a pharmaceutically acceptable carrier.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2013
From: BHAT, BALKRISHEN; MARCUSSON, ERIC
To: REGULUS THERAPEUTICS INC.
Reel/Frame 030430/0138 →
Continuity (4)
Provisional Application 61741783 · Apr 25, 2012
Provisional Application 61717927 · Oct 24, 2012
Provisional Application 61779913 · Mar 13, 2013
Related Publication 20130289093A1 · Oct 31, 2013