IP Library Granted Patent US 9,011,918
Granted Patent B2
US 9,011,918 · App. 13/566,392 · Granted Apr 21, 2015

Biocompatible and biodegradable elastomeric polymers

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Quick Facts
Patent No.
US 9,011,918
App. No.
13/566,392
Granted
Apr 21, 2015
Kind
B2
Abstract

Disclosed herein are biocompatible and biodegradable polymers which are useful in tissue engineering, wound healing, coatings, and drug delivery, the polymers comprising one or more ECM-mimetic peptides and one or more biodegradable moieties, wherein the moieties do not comprise an amino acid or residue thereof. Further disclosed herein are methods for making and using the disclosed biocompatible polymers.

Claims (124)

1. A biocompatible polymer comprising:

a) one or more ECM-mimetic peptides having the amino acid sequence GVGVP as set forth in SEQ ID NO: 29; and

b) one or more biodegradable moieties, wherein the moieties do not comprise an amino acid or residue thereof;

wherein the polymer has a weight-average molecular weight of from about 1,000 Da to about 2,000,000 Da.

2. A biocompatible polymer comprising:

a) one or more ECM-mimetic peptides; and

b) one or more biodegradable moieties, wherein the moieties do not comprise an amino acid or residue thereof;

wherein the polymer has a weight-average molecular weight of from about 1,000 Da to about 2,000,000 Da having the formula:

wherein:

Mim is the ECM-mimetic peptide having the formula:

-[Xaa-Xbb-Xcc] x ; or

-[Xaa-Xbb-Xcc-Xdd] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff-Xgg] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff-Xgg-Xhh] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff-Xgg-Xhh-Xii] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff-Xgg-Xhh-Xii-Xjj] x ; or

-[Xaa-Xbb-Xcc-Xdd-Xee-Xff-Xgg-Xhh-Xii-Xjj-Xkk] x;

wherein:

at least one of Xaa, Xbb, Xcc, Xdd, Xee, Xff, Xgg, Xhh, Xii, Xjj, and Xkk is a proline residue; the balance of Xaa, Xbb, Xcc, Xdd, Xee, Xff, Xgg, Xhh, Xii, Xjj, and Xkk are independently chosen from glycine, alanine, valine, leucine, and isoleucine;

wherein BioDeg is the non-amino acid or residue thereof containing one or more biodegradable moieties;

the index x is an integer from 1 to 30;

the index y is an integer from 1 to 10;

the index z is an integer from 1 to 2000;

wherein L is a biodegradable or non-biodegradable linker;

and wherein the one or more ECM-mimetic peptides are chosen from:

[SEQ ID NO: 61]

i)

Gly- Val-Pro-Gly-Val-Gly -Gly;

[SEQ ID NO: 62]

ii)

Pro-Gly- Val-Pro-Gly-Val-Gly -Gly;

[SEQ ID NO: 63]

iii)

Gly- Val-Pro-Gly-Val-Gly -Leu-Ala;

[SEQ ID NO: 64]

iv)

Val-Gly- Val-Pro-Gly-Val-Gly -Ile-Gly;

[SEQ ID NO: 65]

v)

Gly-Val-Gly- Val-Pro-Gly-Val-Gly -Gly;

[SEQ ID NO: 66]

vi)

Gly- Val-Pro-Gly-Val-Gly -Leu-Leu;

[SEQ ID NO: 67]

vii)

Gly-Gly-Gly- Val-Pro-Gly-Val-Gly -Gly-Gly;

[SEQ ID NO: 68]

viii)

Gly-Gly- Val-Pro-Gly-Val-Gly -Gly-Ala-Ala;

[SEQ ID NO: 69]

ix)

Pro-Pro-Gly- Val-Pro-Gly-Val-Gly -Gly-Gly-

Pro;

[SEQ ID NO: 70]

x)

Ala- Val-Pro-Gly-Val-Gly -Ala;

[SEQ ID NO: 71]

xi)

Ala-Ala- Val-Pro-Gly-Val-Gly -Ala;

[SEQ ID NO: 72]

xii)

Ala- Val-Pro-Gly-Val-Gly -Ala-Ala;

[SEQ ID NO: 73]

xiii)

Ala-Ala- Val-Pro-Gly-Val-Gly -Ala-Ala;

[SEQ ID NO: 74]

xiv)

Ala-Leu-Ala- Val-Pro-Gly-Val-Gly -Ala;

[SEQ ID NO: 75]

xv)

Ala- Val-Pro-Gly-Val-Gly -Ala-Ile-Ile;

[SEQ ID NO: 76]

xvi)

Gly-Val-Gly- Val-Pro-Gly-Val-Gly -Gly-Val;

[SEQ ID NO: 77]

xvii)

Ala-Ala- Val-Pro-Gly-Val-Gly -Ala-Ala-Ala;

[SEQ ID NO: 78]

xviii)

Ala-Ala-Ala- Val-Pro-Gly-Val-Gly -Ala-Ala-

Ala;

and

[SEQ ID NO: 29]

xix)

Gly-Val-Gly-Val-Pro;.

3. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is an integer from 1 to 10.

4. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

5. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

6. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

7. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

8. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

9. The polymer according to claim 2 , wherein the linker has the formula:

and the index t is from 1 to 10.

10. A method for preparing a biocompatible polymer comprising:

i) one or more ECM-mimetic peptides having the amino acid sequence GVGVP as set forth in SEQ ID No: 29; and

ii) one or more biodegradable moieties, wherein the moieties do not comprise an amino acid or residue thereof;

wherein the polymer has a weight-average molecular weight of from about 1,000 Da to about 2,000,000 Da,

comprising:

a) providing an ECM-mimetic peptide-comprising reagent having the formula:

H 2 N-G-V-G-V-P-OH [SEQ ID No: 29];

b) coupling a biodegradable reagent that does not comprise an amino acid or residue thereof to the ECM-mimetic peptide-comprising reagent of step (a); and

c) polymerizing the product of step (b).

11. A method for preparing a biocompatible polymer comprising:

i) one or more ECM-mimetic peptides having the amino acid sequence GVGVP as set forth in SEQ ID No: 29; and

ii) one or more biodegradable moieties, wherein the moieties do not comprise an amino acid or residue thereof;

wherein the polymer has a weight-average molecular weight of from about 1,000 Da to about 2,000,000 Da,

comprising:

a) providing an ECM-mimetic peptide-comprising reagent having the formula:

H 2 N-(G-V-G-V-P) x -OH [SEQ ID No: 29];

and the index x is an integer from 1 to 100;

b) coupling a biodegradable reagent that does not comprise an amino acid or residue thereof to the ECM-mimetic peptide-comprising reagent of step (a); and

c) polymerizing the product of step (b).

12. An article comprising the biocompatible polymer of claim 2 .

13. The article of claim 12 , wherein the article is a stent, implant, film, foam, sponge, patch, matrix, fabric, mesh, membrane, or felt.

14. The article of claim 12 , wherein the article is a stent that is coated with the biocompatible polymer.

15. The article of claim 14 , further comprising a bioactive agent.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2025
From: EVONIK CORPORATION
To: EVONIK OPERATIONS GMBH
Reel/Frame 071152/0488 →
CHANGE OF NAME Recorded May 30, 2013
From: EVONIK DEGUSSA CORPORATION
To: EVONIK CORPORATION
Reel/Frame 030517/0880 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2012
From: PATTANAIK, ASIMA
To: EVONIK DEGUSSA CORPORATION
Reel/Frame 029487/0985 →