Synthesis and characterization of photocurable elastomers from poly(glycerol-co-sebacate).

Elastomeric networks are increasingly being investigated for a variety of biomedical applications including drug delivery and tissue engineering. However, in some cases, their preparation requires the use of harsh processing conditions (e.g., high temperature), which limits their biomedical application. Herein, we demonstrate the ability to form elastomeric networks from poly(glycerol-co-sebacate) acrylate (PGSA) under mild conditions while preserving a wide range of physical properties. These networks presented a Young's modulus between 0.05 and 1.38 MPa, an ultimate strength from 0.05 to 0.50 Mpa, and elongation at break between 42% and 189% strain, by varying the degree of acrylation (DA) of PGSA. The in vitro enzymatic and hydrolytic degradation of the polymer networks was dependent on the DA. The copolymerization of poly(ethylene glycol) diacrylate with PGSA allowed for an additional control of mechanical properties and swelling ratios in an aqueous environment, as well as enzymatic and hydrolytic degradation. Photocured PGSA networks demonstrated in vitro biocompatibility as judged by sufficient human primary cell adherence and subsequent proliferation into a confluent monolayer. These photocurable degradable elastomers could have potential application for the encapsulation of temperature-sensitive factors and cells for tissue engineering.

[1]  Joseph P Vacanti,et al.  Biocompatibility analysis of poly(glycerol sebacate) as a nerve guide material. , 2005, Biomaterials.

[2]  J. Vacanti,et al.  Tissue engineering : Frontiers in biotechnology , 1993 .

[3]  K. Woodhouse,et al.  Understanding the biodegradation of polyurethanes: from classical implants to tissue engineering materials. , 2005, Biomaterials.

[4]  J. Hubbell,et al.  Characterization of permeability and network structure of interfacially photopolymerized poly(ethylene glycol) diacrylate hydrogels. , 1998, Biomaterials.

[5]  J. Santerre,et al.  Enzyme induced biodegradation of polycarbonate-polyurethanes: dose dependence effect of cholesterol esterase. , 2003, Biomaterials.

[6]  J. A. Hubbell,et al.  Comparison of covalently and physically cross-linked polyethylene glycol-based hydrogels for the prevention of postoperative adhesions in a rat model. , 1995, Biomaterials.

[7]  F. Gu,et al.  Sustained interferon-gamma delivery from a photocrosslinked biodegradable elastomer. , 2005, Journal of controlled release : official journal of the Controlled Release Society.

[8]  S L Woo,et al.  An in vitro mechanical and histological study of acute stretching on rabbit tibial nerve , 1990, Journal of orthopaedic research : official publication of the Orthopaedic Research Society.

[9]  D. Charlton,et al.  Polymerization efficiency of LED curing lights. , 2002, Journal of esthetic and restorative dentistry : official publication of the American Academy of Esthetic Dentistry ... [et al.].

[10]  G. Qi,et al.  Acryloyl chloride polymer , 1998 .

[11]  R. Langer,et al.  A tough biodegradable elastomer , 2002, Nature Biotechnology.

[12]  Robert Langer,et al.  In vivo degradation characteristics of poly(glycerol sebacate). , 2003, Journal of biomedical materials research. Part A.

[13]  J. Feijen,et al.  Copolymers of trimethylene carbonate and epsilon-caprolactone for porous nerve guides: synthesis and properties. , 2001, Journal of biomaterials science. Polymer edition.

[14]  J. Elisseeff,et al.  Photoencapsulation of chondrocytes in poly(ethylene oxide)-based semi-interpenetrating networks. , 2000, Journal of biomedical materials research.

[15]  Jan Feijen,et al.  Biodegradable elastomeric scaffolds for soft tissue engineering. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[16]  M. Shoichet,et al.  Peripheral nerve regeneration through guidance tubes , 2004, Neurological research.

[17]  G. Lundborg Alternatives to autologous nerve grafts. , 2004, Handchirurgie, Mikrochirurgie, plastische Chirurgie : Organ der Deutschsprachigen Arbeitsgemeinschaft fur Handchirurgie : Organ der Deutschsprachigen Arbeitsgemeinschaft fur Mikrochirurgie der Peripheren Nerven und Gefasse : Organ der V....

[18]  G. L. Woo,et al.  Synthesis and characterization of a novel biodegradable antimicrobial polymer. , 2000, Biomaterials.

[19]  C. Davidson,et al.  Light initiation of dental resins: dynamics of the polymerization. , 1996, Biomaterials.

[20]  B. Amsden,et al.  In vivo degradation behavior of photo-cross-linked star-poly(epsilon-caprolactone-co-D,L-lactide) elastomers. , 2006, Biomacromolecules.

[21]  Guillermo Antonio Ameer,et al.  Novel Citric Acid‐Based Biodegradable Elastomers for Tissue Engineering , 2004 .

[22]  F. Gu,et al.  Sustained interferon-γ delivery from a photocrosslinked biodegradable elastomer , 2005 .

[23]  Kristi S. Anseth,et al.  New Directions in Photopolymerizable Biomaterials , 2002 .

[24]  Elazer R Edelman,et al.  Tissue Engineering Therapy for Cardiovascular Disease , 2003, Circulation research.

[25]  J. Vacanti,et al.  Tissue engineering. , 1993, Science.

[26]  Shiro Kobayashi,et al.  Enzymatic synthesis and curing of biodegradable crosslinkable polyesters , 2002 .

[27]  J. Feijen,et al.  Preparation of degradable porous structures based on 1,3-trimethylene carbonate and D,L-lactide (co)polymers for heart tissue engineering. , 2003, Tissue engineering.

[28]  J. Feijen,et al.  Copolymers of trimethylene carbonate and ε-caprolactone for porous nerve guides: Synthesis and properties , 2001 .

[29]  F. Gillespie,et al.  Ultra-violet absorption by two ultra-violet activated sealants. , 1978, Journal of oral rehabilitation.

[30]  Jian Yang,et al.  Synthesis and evaluation of poly(diol citrate) biodegradable elastomers. , 2006, Biomaterials.

[31]  Joseph P Vacanti,et al.  Dynamic rotational seeding and cell culture system for vascular tube formation. , 2003, Tissue engineering.

[32]  J. Dordick,et al.  Biocatalytic synthesis of highly ordered degradable dextran-based hydrogels. , 2005, Biomaterials.