Abstract
Novel side chain dendronized polyurethane was synthesized by the sequential conjugation of amine-terminated fourth generation polyester dendrons with carboxyl groups at the side chain of polyurethane and deprotection of acetonide groups at the surface of dendrons. The effect of each step on the properties of the polymers was measured by GPC, DSC, SEM, AFM, and water contact angle measurement. The results showed that immobilization of polyester dendrons improve the compatibility of hard and soft segments in polyurethane and decrease the tendency of crystallinity due to the bulkiness of the substituents. After deprotection of the acetonide groups, both bulk and surface hydrophilicity of the polymer were evidently enhanced. Cell toxicity analysis showed that the side chain dendronized polyurethane synthesized in this study has exhibited excellent biocompatibility to human embryonic kidney 293T cells. The cells can effectively adhere to and proliferate on the surface of the polymer film. Overall, the present study demonstrated an efficient modification method for polyurethanes to improve their cell compatibility with high potential in biomedical applications.
Similar content being viewed by others
References
Santerre JP, Woodhouse K, Laroche G, Labow RS (2005) Understanding the biodegradation of polyurethanes: from classical implants to tissue engineering materials. Biomaterials 26:7457
Anne S, Ajay DP, Lynn MF, Laura APW (2008) Biostability and biological performance of a PDMS-based polyurethane for controlled drug release. Biomaterials 29:2987
Matthew RW, Richard B, Cay K (2006) PCL-CPU composite vascular scaffold production for vascular tissue engineering: attachment, proliferation and bioactivity of human vascular endothelial cells. Biomaterials 27:3608
Gerard L, Joan C, Ronda MG, Virginia C (2007) Poly(ether urethane) networks from renewable resources as candidate biomaterials: synthesis and characterization. Biomacromolecules 8:686
Sibylle G, Laszlo K, Katarzyna G, Sylwester G, Mauro A (2003) The use of biodegradable polyurethane scaffolds for cartilage tissue engineering: potential and limitations. Biomaterials 24:5163
Li YH, Huang YD (2007) The study of collagen immobilization on polyurethane by oxygen plasma treatment to enhance cell adhesion and growth. Surf Coat Technol 201:5124
Ryeon H, Baek HS, Lee MH, Woo YI, Han DW, Han MH, Baik HK, Choi WS, Park KD, Chung KH, Park JC (2008) Surface modification for enhancing behaviors of vascular endothelial cells onto polyurethane films by microwave-induced argon plasma. Surf Coat Technol 202:5768
Bo-Lennart J, Anders L, Anette O, Åke Ö (2002) Characterization of air plasma-treated polymer surfaces by ESCA and contact angle measurements for optimization of surface stability and cell growth. J Appl Polym Sci 86:2618
Van Wachem PB, Hendriks M, Blaauw EH, Dijk F, Verhoeven MLPM, Cahalan PT, Van Luyn MJA (2002) (Electron) microscopic observations on tissue integration of collagen-immobilized polyurethane. Biomaterials 23:1401
Zhu YB, Gao CY, He T, Shen JC (2004) Endothelium regeneration on luminal surface of polyurethane vascular scaffold modified with diamine and covalently grafted with gelatin. Biomaterials 25:423
Lin HB, Sun W, Deane FM, Carlos G, Kenneth S, Peter IL, Stuart LC (1994) Synthesis, surface, and cell-adhesion properties of polyurethanes containing covalently grafted RGD-peptides. J Biomed Mater Res 28:329
Duncan R, Izzo L (2005) Dendrimer biocompatibility and toxicity. Adv Drug Deliv Rev 57:2215
Gillies ER, Dy E, Frchet JMJ, Szoka FC (2005) Biological evaluation of polyester dendrimer: poly(ethylene oxide) “bow-tie” hybrids with tunable molecular weight and architecture. Mol Pharm 2:129
Frauenrath H (2005) Dendronized polymers—building a new bridge from molecules to nanoscopic objects. Prog Polym Sci 30:325
Tian L, Hammond PT (2006) Comb-dendritic block copolymers as tree-shaped macromolecular amphiphiles for nanoparticle self-assembly. Chem Mater 18:3976
Malkoch M, Malmstrom E, Hult A (2002) Rapid and efficient synthesis of aliphatic ester dendrons and dendrimers. Macromolecules 35:8307
Wang SF, Kempen DH, Simha NK, Lewis JL, Windebank AJ, Yaszemski MJ, Lu LC (2008) Photo-cross-linked hybrid polymer networks consisting of poly(propylene fumarate) and poly(caprolactone fumarate): controlled physical properties and regulated bone and nerve cell responses. Biomacromolecules 9:1229
François B, Pitois O, François J (1995) Polymer films with a self-organized honeycomb morphology. Adv Mater 7:1041
Widawski G, Rawiso B, François B (1994) Self-organized honeycomb morphology of star-polymer polystyrene films. Nature 369:387
Sun T, Wang G, Feng L, Liu B, Ma Y, Jiang L, Zhu D (2004) Reversible switching between superhydrophilicity and superhydrophobicity. Angew Chem Int Ed 43:357
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rao, J., Gong, F., Cheng, S. et al. Novel side chain dendronized polyurethane: synthesis, characteristics, and cell responses. Polym. Bull. 62, 867–879 (2009). https://doi.org/10.1007/s00289-009-0058-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-009-0058-7