Toward degradable poly(ester) materials: Investigations into the use of reductive amination and oxime chemistries for crosslinking

PMSE 460

Brooke A. Van Horn, bavanhor@artsci.wustl.edu, Center for Materials Innovation, Department of Chemistry and Department of Radiology, Washington University in Saint Louis, One Brookings Drive, Saint Louis, MO 63130 and Karen L. Wooley, klwooley@artsci.wustl.edu, Center for Materials Innovation and Department of Chemistry, Washington University in Saint Louis, Campus Box 1134, One Brookings Drive, Saint Louis, MO 63130-4899.
Functional poly(ester) materials, having potential biomedical utility in drug delivery and tissue engineering, are the target of many avenues of current research. This presentation discusses our recent investigations into the use of reductive amination and oxime chemistries in the solution-state crosslinking of linear copolymers of å-caprolactone (CL) and 2-oxepane-1,5-dione (OPD), which bear reactive ketone units in addition to the aliphatic ester linkages, to form degradable nanoparticles and gel films. The P(CL-co-OPD) random copolymers were prepared through the ring opening polymerization of CL and TOSUO (1,4,8-trioxaspiro[4.6]-9-undecanone) and subsequent ketal deprotection. The compatibility of these reductive amination and oxime chemistries with the poly(ester) backbone was evaluated through reactions of the P(CL-co-OPD) copolymers with either amine or aminooxy small molecule crosslinkers and monofunctional agents in various solutions, with characterization by 1H and 13C nuclear magnetic resonance (NMR) and infrared (IR) spectroscopies, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA).
 

Polymers for Biomedical Applications
8:30 AM-12:00 PM, Wednesday, 13 September 2006 San Francisco Marriott -- Salon B1, Oral

Division of Polymeric Materials: Science & Engineering

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006