Methods for post-fabrication functionalization of poly(ester ureas)

US9988492B2 · kind B2 · utility

Assignee

• THE UNIVERSITY OF AKRON · US

Inventors

• Matthew Becker · Stow, US
• Fei Lin · Akron, US

Key dates

• Filing date: Sep 30, 2014
• Grant date: Jun 5, 2018
• Expiry date: Dec 29, 2034

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C08G2230/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Amino acid-based poly(ester urea)s (PEU) are emerging as a class of polymers that have shown promise in regenerative medicine applications. Embodiments of the invention relate to the synthesis of PEUs carrying pendent “clickable” groups on modified tyrosine amino acids. The pendent species include alkyne, azide, alkene, tyrosine-phenol, and ketone groups. PEUs with Mw exceeding 100k Da were obtained via interfacial polycondensation methods and the concentration of pendent groups was varied by copolymerization. The incorporation of derivatizable functionalities is demonstrated using 1H NMR and UV-Vis spectroscopy methods. Electrospinning was used to fabricate PEU nanofibers with a diameters ranging from 350 nm to 500 nm. The nanofiber matricies possess mechanical strengths suitable for tissue engineering (Young's modulus: 300±45 MPa; tensile stress: 8.5±1.2 MPa). A series of bioactive peptides and fluorescent molecules were conjugated to the surface of the nanofibers following electrospinning using bio-orthogonal reactions in aqueous media.