IP Library › Granted Patent US 8,795,691

Granted Patent B2

US 8,795,691 · App. 13/634,340 · Granted Aug 5, 2014

Nanotubes and compositions thereof

Inventors: Thomas J. Webster (Barrington, RI); Hicham Fenniri (Edmonton, CA); Usha Devi Hemraz (Edmonton, CA)

Assignees: Brown University; National Research Council of Canada; The Governors of the University of Alberta

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Quick Facts

Patent No.: US 8,795,691
App. No.: 13/634,340
Granted: Aug 5, 2014
Kind: B2

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USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present invention is directed to implants and the modification of the surface of implants using amino acid or polypeptide functionalized rosette nanotubes.

Claims (69)

1. A method of promoting osteoblast differentiation and proliferation at a site of a bone injury or defect or bone surgical site comprising providing an implant having a composition including nanotubes formed from modules according to Formula II, nanoparticles, and a matrix material, and optionally nanotubes formed from modules according to Formula I wherein Formula II is

wherein X is CH or nitrogen; Y is lysine-arginine-serine-arginine, isoleucine-lysine-valine-alanine-valine or tyrosine-isoleucine-glycine-serine-arginine; R 2 is absent or a linker and R 1 is aliphatic, and

wherein Formula I is

placing the implant at the site of a bone injury or defect or bone surgical site.

2. The method of claim 1 wherein R 2 is NH 3 + ,

(CH 2 ) 3 CO or (CH 2 )n where n is an integer of 1, 2, 3, or 4.

3. The method of claim 1 where R 1 is C 1 to C 10 alkyl, straight or branched chain, saturated or unsaturated.

4. The method of claim 1 wherein the nanoparticles are nanoparticles of calcium phosphate, hydroxyapatite, apatite, oxyapatite, octacalcium phosphate, monocalcium phosphate, dicalcium phosphate, tricalcium phosphate, β-tricalcium phosphate, α-tricalcium phosphate, tetracalcium phosphate, calcium hydrogen phosphate or calcium dihydrogen phosphate.

5. The method of claim 1 wherein the matrix material is one or more of polylactic acid, polylactide-coglycolide, polyglycolic acid, polymethylmethacrylate, polyurethane, polycaprolactone, polyethylene, polystyrene, polypropylene, polypyrrole, or poly(2-hydroxyethyl methacrylate).

6. The method of claim 1 wherein Formula I is absent, X is N, R 1 is methyl, R 2 is (CH 2 ) 3 CO, Y is lysine-arginine-serine-arginine, the nanoparticles are nanoparticles of hydroxyapatite, and the matrix material is poly(2-hydroxyethylmethacrylate).

7. A compound having the formula

wherein X is CH or nitrogen; Y is lysine-arginine-serine-arginine, isoleucine-lysine-valine-alanine-valine or tyrosine-isoleucine-glycine-serine-arginine; and R 1 is C1 to C10 alkyl, straight or branched chain, saturated or unsaturated; and salts thereof.

8. A compound having the formula

wherein X is CH or nitrogen; n is an integer of, 1, 2, 3, or 4; Y is lysine-arginine-serine-arginine, isoleucine-lysine-valine-alanine-valine or tyrosine-isoleucine-glycine-serine-arginine; and R 1 is C1 to C10 alkyl, straight or branched chain, saturated or unsaturated; and salts thereof.

9. A structure formed from the self-assembly in aqueous media of compounds having the formula

10. A structure formed from the self-assembly in aqueous media of compounds having the formula

11. A structure formed from the self-assembly in aqueous media of one or more compounds having the formula

and one or more compounds having the formula

12. A method of forming a nanotube comprising placing in an aqueous media compounds having the formula

13. A method of forming a nanotube comprising placing in an aqueous media compounds having the formula

14. A method of making an implant comprising coating an implant with a nanotube formed from compounds having the formula

15. A method of making an implant comprising coating an implant with a nanotube formed from compounds having the formula

16. A method of making an implant comprising coating an implant with a nanotube formed from one or more compounds having the formula

and one or more compounds having the formula

17. A method of promoting growth of tissue at the site of an implant comprising implanting an implant having a coating of nanotubes formed from compounds having the formula

18. A method of promoting growth of tissue at the site of an implant comprising implanting an implant having a coating of nanotubes formed from compounds having the formula

19. A method of promoting growth of tissue at the site of an implant comprising implanting an implant having a coating of nanotubes formed from one or more compounds having the formula

and one or more compounds having the formula

20. A composition comprising nanotubes, a compound for providing mechanical strength and a matrix material, wherein the nanotubes are formed from one or more compounds having Formula II

or one or more compounds having Formula I

21. The composition of claim 20 wherein R 2 is NH 3 + ,

(CH 2 ) 3 CO or (CH 2 )n where n is an integer of 1, 2, 3, or 4.

22. The composition of claim 20 where R 1 is C 1 to C 10 alkyl, straight or branched chain, saturated or unsaturated.

23. The composition of claim 20 wherein the compound for providing mechanical strength is a nanoparticle of calcium phosphate, hydroxyapatite, apatite, oxyapatite, octacalcium phosphate, monocalcium phosphate, dicalcium phosphate, tricalcium phosphate, β-tricalcium phosphate, α-tricalcium phosphate, tetracalcium phosphate, calcium hydrogen phosphate or calcium dihydrogen phosphate.

24. The composition of claim 20 wherein the matrix material is one or more of polylactic acid, polylactide-coglycolide, polyglycolic acid, polymethylmethacrylate, polyurethane, polycaprolactone, polyethylene, polystyrene polypropylene, polypyrrole, or poly(2-hydroxyethyl methacrylate).

25. The composition of claim 20 wherein Formula I is absent, X is N, R 1 is methyl, R 2 is (CH 2 ) 3 CO, Y is lysine-arginine-serine-arginine, the compound for providing mechanical strength is a nanoparticle of hydroxyapatite, and the matrix material is poly(2-hydroxyethylmethacrylate).

26. The method of claim 1 wherein the implant is an injectable liquid, moldable putty or hardened structure.

27. The composition of claim 20 wherein the composition is an injectable liquid, moldable putty or hardened structure.

28. The method of claim 1 wherein the implant is a porous hardened structure.

29. The method of claim 1 wherein the implant is a nonporous hardened structure.

30. The composition of claim 20 the composition is in the form of a porous hardened structure.

31. The composition of claim 20 the composition is in the form of a nonporous hardened structure.

32. The method of claim 1 wherein the implant is a plate, rod, screw, cage, scaffold or film.

33. The composition of claim 20 wherein the composition is in the form of a plate, rod, screw, cage, scaffold, film or coating.

34. The method of claim 17 wherein the site of the implant is bone, cartilage, vascular tissue, heart tissue, cardiovascular tissue, bladder tissue, nervous system tissue, skin tissue, spine, a periodontal defect, a dental extraction socket, a cystic defect, a sinus, an alveolar ridge, an oral site, a maxillofacial site or an orthopedic site.

35. The method of claim 18 wherein the site of the implant is bone, cartilage, vascular tissue, heart tissue, cardiovascular tissue, bladder tissue, nervous system tissue, skin tissue, spine, a periodontal defect, a dental extraction socket, a cystic defect, a sinus, an alveolar ridge, an oral site, a maxillofacial site or an orthopedic site.

36. The method of claim 19 wherein the site of the implant is bone, cartilage, vascular tissue, heart tissue, cardiovascular tissue, bladder tissue, nervous system tissue, skin tissue, spine, a periodontal defect, a dental extraction socket, a cystic defect, a sinus, an alveolar ridge, an oral site, a maxillofacial site or an orthopedic site.

37. The method of claim 1 wherein the matrix material is a curable matrix material.

38. The composition of claim 20 wherein the matrix material is a curable matrix material.

39. The method of claim 17 wherein the growth of tissue comprises expansion and growth of cells into tissue wherein the cells are osteoblasts, fibroblasts, endothelial cells, keratinocytes, cardiac myocytes, chondrocytes, synoviocytes, mesenchymel stem cells, neural stem cells, islet cells, hepatocytes, smooth muscle cells, urothelial cells, neurons or Schwann cells.

40. The method of claim 18 wherein the growth of tissue comprises expansion and growth of cells into tissue wherein the cells are osteoblasts, fibroblasts, endothelial cells, keratinocytes, cardiac myocytes, chondrocytes, synoviocytes, mesenchymel stem cells, neural stem cells, islet cells, hepatocytes, smooth muscle cells, urothelial cells, neurons or Schwann cells.

41. The method of claim 19 wherein the growth of tissue comprises expansion and growth of cells into tissue wherein the cells are osteoblasts, fibroblasts, endothelial cells, keratinocytes, cardiac myocytes, chondrocytes, synoviocytes, mesenchymel stem cells, neural stem cells, islet cells, hepatocytes, smooth muscle cells, urothelial cells, neurons or Schwann cells.

Assignments (5)

CONFIRMATORY LICENSE Recorded Feb 10, 2015

From: BROWN UNIVERSITY

To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT

Reel/Frame 034926/0350 →

CONFIRMATORY LICENSE Recorded Feb 25, 2014

From: BROWN UNIVERSITY

To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT

Reel/Frame 032333/0505 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2012

From: WEBSTER, THOMAS J.

To: BROWN UNIVERSITY