Phosphorylcholine end-capped poly-ε-caprolactone: A novel biodegradable material with improved antiadsorption property

In this study, the synthesis, characterization, and properties of a novel biodegradable polymer with improved hemocompatibility were introduced. It was synthesized by end-capping poly-e-caprolactone (PCL) with phosphorylcholine (PC) groups. The polyester backbone provided the mechanical stability and biodegradability, while the PC-end groups improved its hemocompatibility. The obtained polymer was characterized using 1H NMR, 31P NMR, FTIR, and GPC, its crystallization behavior was studied by DSC. Compared with original PCL, the resulting polymer (PC-PCL) showed a lower crystallization capability and a faster degradation rate in PBS. The degradation rate of the polymer blends of PCL/PC-PCL increased with increasing PC-PCL content. The results of water contact angle measurements revealed a more hydrophilic surface property of PC-PCL than neat PCL. The hemocompatibility of PC-PCL was estimated using rabbit platelet-rich plasma, a better resistance to platelet adhesion and activation was observed. During the human blood plasma contacting process, PC-PCL showed a prolonged activated partial thromboplastin time over neat PCL. Material–cell interaction was evaluated with human umbilical vein endothelial cell, the result indicated that PC-PCL may to some extent have an antihyperplasia property, compared with neat PCL. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 989–997, 2007

[1]  B. Nilsson,et al.  Phosphoryl choline introduces dual activity in biomimetic ionomers. , 2004, Journal of the American Chemical Society.

[2]  J. Hilborn,et al.  Synthesis, Characterization and Properties of Phosphoryl Choline Functionalized Poly e-caprolactone and Charged Phospholipid Analogues , 2004 .

[3]  A. Lloyd,et al.  The effect of phosphorylcholine-coated materials on the inflammatory response and fibrous capsule formation: in vitro and in vivo observations. , 2004, Journal of biomedical materials research. Part A.

[4]  T. D. Fornes,et al.  Crystallization behavior of nylon 6 nanocomposites , 2003 .

[5]  D. Wise,et al.  Antinociceptive effects of hydromorphone, bupivacaine and biphalin released from PLGA polymer after intrathecal implantation in rats. , 2003, Biomaterials.

[6]  Y. Iwasaki,et al.  Reduced adhesion of blood cells to biodegradable polymers by introducing phosphorylcholine moieties. , 2003, Journal of biomedical materials research. Part A.

[7]  A. Albertsson,et al.  Synthesis and in vitro degradation of poly(N‐vinyl‐2‐pyrrolidone)‐based graft copolymers for biomedical applications , 2002 .

[8]  J. Watanabe,et al.  Biocompatible polymer alloy membrane for implantable artificial pancreas , 2002 .

[9]  A. Mochizuki,et al.  Study of blood compatibility with poly(2-methoxyethyl acrylate). Relationship between water structure and platelet compatibility in poly(2-methoxyethylacrylate-co-2-hydroxyethylmethacrylate). , 2002, Biomacromolecules.

[10]  Alyssa Panitch,et al.  Polymeric biomaterials for tissue and organ regeneration , 2001 .

[11]  C. Schmidt,et al.  Vascular graft endothelialization: comparative analysis of canine and human endothelial cell migration on natural biomaterials. , 2001, Journal of biomedical materials research.

[12]  A. Lewis,et al.  Crosslinkable coatings from phosphorylcholine-based polymers. , 2001, Biomaterials.

[13]  R. P. Redman,et al.  Synthesis and characterisation of phosphorylcholine-based polymers useful for coating blood filtration devices. , 2000, Biomaterials.

[14]  E. Murphy,et al.  Characterization of protein adsorption at the phosphorylcholine incorporated polymer-water interface , 2000 .

[15]  W. Bonfield,et al.  Biodegradable drug delivery system for the treatment of bone infection and repair , 1999, Journal of materials science. Materials in medicine.

[16]  Yue Zhao,et al.  Crystallization under Strain and Resultant Orientation of Poly(ε-caprolactone) in Miscible Blends , 1999 .

[17]  K A Schafer,et al.  The Cell Cycle: A Review , 1998, Veterinary pathology.

[18]  K. Smith,et al.  A review of tumor suppressor genes in cutaneous neoplasms with emphasis on cell cycle regulators. , 1998, The American Journal of dermatopathology.

[19]  R. Franke,et al.  Biocompatibility analysis of different biomaterials in human bone marrow cell cultures. , 1998, Journal of Biomedical Materials Research.

[20]  N Nakabayashi,et al.  Why do phospholipid polymers reduce protein adsorption? , 1998, Journal of biomedical materials research.

[21]  Yu-jun Li,et al.  Synthesis and characterization of polyurethanes containing cholesterol and phosphatidylcholine analogous moieties , 1995 .

[22]  Yu-jun Li,et al.  Synthesis of Novel Organopolysiloxanes Having a Phospholipid-like Structure , 1995 .

[23]  Yu-jun Li,et al.  Synthesis and properties of polyurethanes containing phosphatidylcholine analogues in the polymer backbone , 1995 .

[24]  J M Anderson,et al.  Protein adsorption from human plasma is reduced on phospholipid polymers. , 1991, Journal of biomedical materials research.

[25]  A Watanabe,et al.  Interaction between phospholipids and biocompatible polymers containing a phosphorylcholine moiety. , 1991, Biomaterials.

[26]  N Nakabayashi,et al.  Reduced thrombogenicity of polymers having phospholipid polar groups. , 1990, Journal of biomedical materials research.

[27]  Kazuhiko Ishihara,et al.  Preparation of Phospholipid Polylners and Their Properties as Polymer Hydrogel Membranes , 1990, Polymer Journal.

[28]  D. Chapman,et al.  Biomembranes as models for polymer surfaces. V. Thrombelastographic studies of polymeric lipids and polyesters. , 1989, Biomaterials.

[29]  T. Nakaya,et al.  Polymeric phospholipid analogues, 14. The convenient preparation of a vinyl monomer containing a phospholipid analogue , 1982 .

[30]  H. J. Lucas,et al.  Cyclic Phosphites of Some Aliphatic Glycols , 1950 .