Peracylated protein-based sutures and fabrics and process for making the same

• US 6,254,986 B1
• Filed: 06/14/2000
• Issued: 07/03/2001
• Est. Priority Date: 12/26/1996
• Status: Expired due to Term

• Current Assignee: Poly-Med, Inc.
• Original Assignee: Poly-Med, Inc.
• Inventors: Corbett, Joel T., Allan, Jacqueline M., Shalaby, Shalaby W.
• Primary Examiner(s): Acquah, Samuel A.
• Application Number:
  US09/593,859
• Time in Patent Office: 384 Days
• Field of Search: 528/486, 528/487, 525/54.11, 525/54.4, 428/357, 428/364, 428/365, 530/342, 530/345, 530/353, 530/357
• US Class Current: 428/365
• CPC Class Codes: C07K 1/113 without change of the primary structure
• CPC Class Codes: C07K 14/415 from plants
• CPC Class Codes: Y10T 428/29 Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
• CPC Class Codes: Y10T 428/2913 Rod, strand, filament or fiber
• CPC Class Codes: Y10T 428/2915 including textile, cloth or fabric

Abstract

A method for modifying a protein or polypeptide is disclosed which includes the steps of dispersing a protein or polypeptide in an essentially non-aqueous medium and peracylating the protein or polypeptide with a cyclic anhydride having a carbon chain substituent selected from the group consisting of alkyl and alkenyl groups. Most preferably, the cyclic anhydride is succinic anhydride, although glutaric anhydride may also be employed. Preferably, the step of peracylating the protein or polypeptide is performed in the presence of an acid catalyst, most preferably ρ-toluene sulfonic acid. The resultant modified protein or polypeptide may be employed in numerous applications including drug delivery, absorbable sutures, and thermoplastic films and molded articles.

Claims

1. A modified suture made by the process comprising the steps of:

providing a protein-based suture, the protein being selected from the group consisting of silk and collagen;

dispersing the protein-based suture in an essentially non-aqueous medium; and

peracylating the protein with at least two acyl groups per protein molecule by reacting the protein with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

2. The modified suture set forth in claim 1 wherein said essentially non-aqueous medium comprises acetic acid.

3. The modified suture set forth in claim 1 wherein said essentially non-aqueous medium comprises propionic acid.

4. The modified suture set forth in claim 1 wherein said acid catalyst comprises ρ

-toluene sulfonic acid.

5. The modified suture set forth in claim 1 wherein said cyclic anhydride comprises succinic anhydride.

6. The modified suture set forth in claim 1 wherein said cyclic anhydride comprises glutaric anhydride.

7. A modified fabric made by the process comprising the steps of:

providing a fabric comprising protein-based fibers selected from the group consisting of silk and wool;

dispersing the fabric in an essentially non-aqueous medium; and

peracylating the protein with at least two acyl groups per protein molecule by reacting the protein with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

8. The modified fabric set forth in claim 7 wherein said essentially non-aqueous medium comprises acetic acid.

9. The modified fabric set forth in claim 7 wherein said essentially non-aqueous medium comprises propionic acid.

10. The modified fabric set forth in claim 7 wherein said acid catalyst comprises ρ

-toluene sulfonic acid.

11. The modified fabric set forth in claim 7 wherein said cyclic anhydride comprises succinic anhydride.

12. The modified fabric set forth in claim 7 wherein said cyclic anhydride comprises glutaric anhydride.

13. A method for modifying a fiber comprising the steps of:

providing a fiber comprising a protein-based polymer selected from the group consisting of collagen, silk and wool;

dispersing the fiber in an essentially non-aqueous medium; and

peracylating the protein with at least two acyl groups per protein molecule by reacting the protein with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

14. The method set forth in claim 13 wherein said cyclic anhydride comprises succinic anhydride.

15. The method set forth in claim 13 wherein said cyclic anhydride comprises glutaric anhydride.

16. The method set forth in claim 13 wherein said acid catalyst comprises ρ

-toluene sulfonic acid.

17. The method set forth in claim 13 wherein said essentially non-aqueous medium comprises acetic acid.

18. The method set forth in claim 13 wherein said essentially non-aqueous medium comprises propionic acid.