title: Biodegradable poly(ester urethane)urea elastomers with variable amino content for subsequent functionalization with phosphorylcholine.
abstract: While surface modification is well suited for imparting biomaterials with specific functionality for favorable cell interactions, the modification of degradable polymers would be expected to provide only temporary benefit. Bulk modification by incorporating pendant reactive groups for subsequent functionalization of biodegradable polymers would provide a more enduring approach. Towards this end, a series of biodegradable poly(ester urethane)urea elastomers with variable amino content (PEUU-NH2 polymers) were developed. Carboxylated phosphorycholine was synthesized and conjugated to the PEUU-NH2 polymers for subsequent bulk functionalization to generate PEUU-PC polymers. Synthesis was verified by proton nuclear magnetic resonance, X-ray photoelectron spectroscopy and attenuated total reflection Fourier transform infrared spectroscopy. The impact of amine incorporation and phosphorylcholine conjugation was shown on mechanical, thermal and degradation properties. Water absorption increased with increasing amine content, and further with PC conjugation. In wet conditions, tensile strength and initial modulus generally decreased with increasing hydrophilicity, but remained in the range of 5-30 MPa and 10-20 MPa, respectively. PC conjugation was associated with significantly reduced platelet adhesion in blood contact testing and the inhibition of rat vascular smooth muscle cell proliferation. These biodegradable PEUU-PC elastomers offer attractive properties for applications as non-thrombogenic, biodegradable coatings and for blood-contacting scaffold applications. Further, the PEUU-NH2 base polymers offer the potential to have multiple types of biofunctional groups conjugated onto the backbone to address a variety of design objectives.
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China; McGowan Institute for Regenerative Medicine, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Surgery, University of Pittsburgh, Pittsburgh, PA 15219, USA.
authors.forename: Jun
authors.initials: J
authors.lastname: Fang
authors.affiliation: McGowan Institute for Regenerative Medicine, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Surgery, University of Pittsburgh, Pittsburgh, PA 15219, USA.
authors.forename: Sang-Ho
authors.initials: SH
authors.lastname: Ye
authors.affiliation: McGowan Institute for Regenerative Medicine, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Surgery, University of Pittsburgh, Pittsburgh, PA 15219, USA.
authors.forename: Venkat
authors.initials: V
authors.lastname: Shankarraman
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA 15261, USA.
authors.forename: Yixian
authors.initials: Y
authors.lastname: Huang
authors.affiliation: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China; College of Chemistry and Chemical Engineering and Biological Engineering, Donghua University, Shanghai 201620, China.
authors.forename: Xiumei
authors.initials: X
authors.lastname: Mo
authors.affiliation: McGowan Institute for Regenerative Medicine, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Surgery, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Chemical Engineering, University of Pittsburgh, Pittsburgh, PA 15219, USA; Department of Bioengineering, University of Pittsburgh, Pittsburgh, PA 15219, USA. Electronic address: wagnerwr@upmc.edu.
authors.forename: William R
authors.initials: WR
authors.lastname: Wagner
mesh_terms: D000588:Amines / Q000737:chemistry*; D000818:Animals; D001672:Biocompatible Materials / Q000737:chemistry / Q000494:pharmacology*; D001792:Blood Platelets / Q000187:drug effects / Q000648:ultrastructure; D002152:Calorimetry, Differential Scanning; D020724:Elastomers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008049:Lipase / Q000494:pharmacology; D008970:Molecular Weight; D032389:Myocytes, Smooth Muscle / Q000166:cytology / Q000187:drug effects; D010767:Phosphorylcholine / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010973:Platelet Adhesiveness / Q000187:drug effects; D011091:Polyesters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D066244:Proton Magnetic Resonance Spectroscopy; D051381:Rats; D012756:Sheep; D012996:Solutions; D012997:Solvents; D017550:Spectroscopy, Fourier Transform Infrared; D013314:Stress, Mechanical; D013499:Surface Properties; D014867:Water / Q000737:chemistry
chemical_list: D000588:Amines; D001672:Biocompatible Materials; D020724:Elastomers; D011091:Polyesters; D012996:Solutions; D012997:Solvents; C497893:poly(ester urethane)urea; D014867:Water; D010767:Phosphorylcholine; D008049:Lipase
keywords: Biodegradable polyurethane; Bulk modification; Cardiovascular biomaterial; Zwitterion