Biodegradable amino-ester nanomaterials for nucleic acid delivery

• US 10,457,631 B2
• Filed: 04/06/2017
• Issued: 10/29/2019
• Est. Priority Date: 04/06/2016
• Status: Active Grant

• Current Assignee: Ohio State Innovation Foundation (Ohio State University)
• Original Assignee: Ohio State Innovation Foundation (Ohio State University)
• Inventors: Dong, Yizhou, Zhang, Xinfu, Luo, Xiao
• Primary Examiner(s): Otton, Alicia L
• Application Number:
  US16/091,062
• Publication Number:
  US 20190119198A1
• Time in Patent Office: 936 Days
• Field of Search: None
• CPC Class Codes: A61K 47/18 Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
• CPC Class Codes: A61K 48/0008 characterised by an aspect of the 'non-active' part of the composition delivered, e.g. wherein such 'non-active' part is not delivered simultaneously with the 'active' part of the composition
• CPC Class Codes: C07C 219/06 having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 219/08 having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C07C 229/04 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 229/16 to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
• CPC Class Codes: C07C 229/24 having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid

Abstract

The present disclosure relates to a series of biodegradable amino-ester lipid-like nanoparticles. In some embodiments, the biodegradable amino-ester lipid-like nanoparticles are used in methods for the delivery of nucleic acids.

Claims

1. A compound of Formula I:

2. The compound of claim 1, wherein at least one R¹ is unsubstituted alkenyl.

3. The compound of claim 2, wherein at least one R¹ is

4. The compound of claim 1, wherein at least one R¹ is unsubstituted alkyl.

5. The compound of claim 4, wherein at least one R¹ is

6. The compound of claim 1, wherein at least one m=7.

7. The compound of claim 1, wherein at least one R¹ is C₆-C₁₀ alkenyl.

8. The compound of claim 1, wherein at least one R¹ is a branched alkenyl.

9. The compound of claim 1, wherein at least one R¹ is C₆-C₁₀ alkyl.

10. The compound of claim 1, wherein at least one R¹ is a branched alkyl.

11. The compound of claim 1, wherein each R¹ is unsubstituted alkenyl.

12. The compound of claim 11, wherein each R¹ is

13. The compound of claim 1, wherein each R¹ is unsubstituted alkyl.

14. The compound of claim 13, wherein each R¹ is

15. The compound of claim 1, wherein each m=7.

16. The compound of claim 1, wherein each R¹ is C₆-C₁₀ alkenyl.

17. The compound of claim 1, wherein each R¹ is C₆-C₁₀ alkyl.

18. The compound of claim 1, wherein each R¹ is a branched alkyl.

19. A composition comprising:

a compound of Formula I;

20. A nanoparticle comprising:

a compound of Formula I;