Multifunctionalized bioactive polycaprolactone

Patent metadata

Field	Value
Publication number	US-10828371-B2
Application number	US-201715806433-A
Country	US
Kind code	B2
Filing date	Nov 8, 2017
Priority date	Nov 8, 2017
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

A multifunctionalized polycaprolactone polymer, a process for forming a multifunctionalized polycaprolactone polymer, and an article of manufacture comprising a material containing a multifunctionalized polycaprolactone polymer are disclosed. The multifunctionalized polycaprolactone polymer includes at least two functional groups. The process of forming the multifunctionalized polycaprolactone polymer includes forming a caprolactone monomer having at least two functional groups, and polymerizing the caprolactone monomer. Further, the article of manufacture includes a polycaprolactone polymer having at least two functional groups.

First claim

What is claimed is:

1. A multifunctionalized polycaprolactone homopolymer with a formula of:

wherein L is a first primary amine group;
wherein L′ is a first hydroxyl group;
wherein M is a second primary amine group;
wherein M′ is selected from the group consisting of a first hydrogen atom, a third primary amine group, and a second hydroxyl group;
wherein M″ is selected from the group consisting of a second hydrogen atom and a fourth primary amine group; and
wherein the multifunctionalized polycaprolactone homopolymer is formed by polymerizing a multifunctionalized caprolactone monomer.

2. The multifunctionalized polycaprolactone polymer of claim 1 , wherein M′ is the third primary amine group and M″ is the fourth primary amine group.

3. The multifunctionalized polycaprolactone polymer of claim 1 , wherein M′ is the second hydroxyl group.

4. The multifunctionalized polycaprolactone homopolymer of claim 1 , wherein M′ is the first hydrogen atom, and M″ is the second hydrogen atom.

5. The multifunctionalized polycaprolactone polymer of claim 1 , wherein M′ is the first hydrogen atom, and M″ is the second hydrogen atom.

6. The multifunctionalized polycaprolactone polymer of claim 1 , wherein M′ is the third primary amine group, and M″ is the second hydrogen atom.

7. The multifunctionalized polycaprolactone polymer of claim 1 , wherein M′ is the second hydroxyl group, and M″ is the fourth primary amine group.

8. An article of manufacture comprising a multifunctionalized polycaprolactone homopolymer with a formula of:

wherein L is a first primary amine group;
wherein L′ is a first hydroxyl group;
wherein M is a second primary amine group;
wherein M′ is selected from the group consisting of a first hydrogen atom, a third primary amine group, and a second hydroxyl group;
wherein, M″ is selected from the group consisting of a second hydrogen atom and a fourth primary amine group; and
wherein the multifunctionalized polycaprolactone homopolymer is formed by polymerizing a multifunctionalized caprolactone monomer.

9. The article of manufacture of claim 8 , further comprising at least one bioactive compound bound to the polycaprolactone homopolymer.

10. The article of manufacture of claim 9 , wherein the bioactive compound is selected from a group consisting of RGD peptides, YIGSR peptides (SEQ ID NO: 1), IKVAV peptides (SEQ ID NO: 2), fibronectin-derived REDV peptides (SEQ ID NO: 3), collagen I mimetic DGEA peptides (SEQ ID NO: 4), osteopontin-derived SVVYGR peptides (SEQ ID NO: 5), elastin-derived VAPG peptides (SEQ ID NO: 6), a peptidomimetic, galactose, lactose, vascular endothelial growth factor, fibronectin domain III 12-14, bone morphogenetic protein 2, dexamethasone, glycerolphosphate, transforming growth factor beta, and basic fibroblast growth factor.

11. The article of manufacture of claim 8 , wherein the article of manufacture is a tissue scaffold.

12. The article of manufacture of claim 8 , wherein the article of manufacture is a drug delivery capsule.

13. A process of forming a multifunctionalized polycaprolactone polymer, comprising: polymerizing a caprolactone monomer to form a polymer having the following structure:

wherein L is a first primary amine group;
wherein L′ is a first hydroxyl group;
wherein M is a second primary amine group;
wherein M′ is selected from the group consisting of a first hydrogen atom, a third primary amine group, and a second hydroxyl group; and
wherein M″ is selected from the group consisting of a second hydrogen atom and a fourth primary amine group.

14. The process of claim 13 , further comprising reacting the multifunctionalized polycaprolactone polymer with a bioactive compound.

15. The process of claim 14 , wherein the bioactive compound is selected from a group consisting of RGD peptides, YIGSR peptides (SEQ ID NO: 1), IKVAV peptides (SEQ ID NO: 2), fibronectin-derived REDV peptides (SEQ ID NO: 3), collagen I mimetic DGEA peptides (SEQ ID NO: 4), osteopontin-derived SVVYGR peptides (SEQ ID NO: 5), elastin-derived VAPG peptides (SEQ ID NO: 6), a peptidomimetic, galactose, lactose, vascular endothelial growth factor, fibronectin domain III 12-14, bone morphogenetic protein 2, dexamethasone, glycerolphosphate, transforming growth factor beta, and basic fibroblast growth factor.

Assignees

• IBM

Inventors

• Campbell Eric J
• Czaplewski-Campbell Sarah K
• Kobilka Brandon M
• Wertz Jason T

Classifications

• C08G63/6822 Primary

  derived from hydroxy carboxylic acids · CPC title

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title

• C08G63/823

  for the preparation of polylactones or polylactides · CPC title

• A61K47/593 Primary

  Polyesters, e.g. PLGA or polylactide-co-glycolide · CPC title

• C08G63/682

  containing halogens · CPC title