Synthesis of Photoreactive Poly(ethylene oxide)s for Surface Modification.

Photoreactive polymers that generate active species upon irradiation with light are very useful for modifying the surfaces of substrates. However, water solubility decreases as the number of photoreactive functional groups on the polymer increases because most photoreactive functional groups are hydrophobic. In order to improve the hydrophilicity of the photoreactive polymer, we synthesized polyethylene glycol-based photoreactive polymers bearing hydrophobic azidophenyl groups on their side chains. Because of the hydrophilicity of the ethylene glycol main chain, polymers with large numbers of azidophenyl groups were solubilized in protic solvents compared to hydrophobic alkylene chain-based polymers prepared by radical polymerization of methacrylate monomers. Polymers were immobilized on various substrates by irradiation with ultraviolet light and were shown to suppress nonspecific interactions between proteins and cells on the substrate. We conclude that such polymers are useful, highly water soluble antifouling agents.

[1]  Sytze J Buwalda,et al.  Synergistic anti-fouling and bactericidal poly(ether ether ketone) surfaces via a one-step photomodification. , 2020, Materials science & engineering. C, Materials for biological applications.

[2]  H. Zuilhof,et al.  Antifouling Polymer Brushes via Oxygen-Tolerant Surface-Initiated PET-RAFT , 2020, Langmuir : the ACS journal of surfaces and colloids.

[3]  Robert Hein,et al.  Antifouling Strategies for Selective In Vitro and In Vivo Sensing. , 2020, Chemical reviews.

[4]  A. Adronov,et al.  Visible Light-Mediated Photoclick Functionalization of a Conjugated Polymer Backbone , 2020 .

[5]  J. Rühe,et al.  Photo-Crosslinking of Thioxanthone Group Containing Copolymers for Surface Modification and Bioanalytics , 2020, Macromolecules.

[6]  G. Hadziioannou,et al.  Photopatternable High-k Fluoropolymer Dielectrics Bearing Pendent Azido Groups , 2019, Macromolecules.

[7]  H. Miyatake,et al.  Cell migration and growth induced by photo-immobilised vascular endothelial growth factor (VEGF) isoforms , 2019, Journal of Materials Chemistry B.

[8]  T. Son,et al.  Photo-reactive natural polymer derivatives for medical application , 2017 .

[9]  T. Okano,et al.  Thermoresponsive-polymer-based materials for temperature-modulated bioanalysis and bioseparations. , 2016, Journal of materials chemistry. B.

[10]  F. Wurm,et al.  Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation. , 2016, Chemical reviews.

[11]  Kemin Wang,et al.  Novel one-component polymeric benzophenone photoinitiator containing poly (ethylene glycol) as hydrogen donor , 2014 .

[12]  H. Frey,et al.  Ferrocenyl glycidyl ether: A versatile ferrocene monomer for copolymerization with ethylene oxide to water-soluble, thermoresponsive copolymers , 2013 .

[13]  U. Schubert,et al.  Homo‐ and diblock copolymers of poly(furfuryl glycidyl ether) by living anionic polymerization: Toward reversibly core‐crosslinked micelles , 2012 .

[14]  Francesco M Veronese,et al.  State of the art in PEGylation: the great versatility achieved after forty years of research. , 2012, Journal of controlled release : official journal of the Controlled Release Society.

[15]  T. Son,et al.  Visible light-induced crosslinkable gelatin. , 2010, Acta biomaterialia.

[16]  Yoshihiro Ito,et al.  Synthesis of a photoimmobilizable histidine polymer for surface modification , 2009 .

[17]  Jie Yin,et al.  A novel amphipathic polymeric thioxanthone photoinitiator , 2009 .

[18]  Paula M Mendes,et al.  Stimuli-responsive surfaces for bio-applications. , 2008, Chemical Society reviews.

[19]  S. Carlotti,et al.  Living/Controlled Anionic Polymerization and Copolymerization of Epichlorohydrin with Tetraoctylammonium Bromide−Triisobutylaluminum Initiating Systems , 2008 .

[20]  Michael Newton,et al.  Progess in superhydrophobic surface development. , 2008, Soft matter.

[21]  Yoshihiro Ito,et al.  Surface modification of plastic, glass and titanium by photoimmobilization of polyethylene glycol for antibiofouling. , 2007, Acta biomaterialia.

[22]  Q. Guo,et al.  Copper-catalyzed synthesis of aryl azides and 1 -aryl -1,2,3 -triazoles from boronic acids , 2007 .

[23]  Yoshihiro Ito,et al.  Photo-immobilization of a phospholipid polymer for surface modification. , 2005, Biomaterials.

[24]  P. Angenendt Progress in protein and antibody microarray technology. , 2005, Drug discovery today.

[25]  K. Koh,et al.  Synthesis of Monodisperse Silica Particles Coated with Well-Defined, High-Density Polymer Brushes by Surface-Initiated Atom Transfer Radical Polymerization , 2005 .

[26]  Yoshihiro Ito,et al.  A Photo-immobilized Allergen Microarray for Screening of Allergen-specific IgE , 2005 .

[27]  Yoshihiro Ito,et al.  Photo-reactive polyvinylalcohol for photo-immobilized microarray. , 2005, Biomaterials.

[28]  O. Kwon,et al.  Co-culture of hepatocytes and fibroblasts by micropatterned immobilization of beta-galactose derivatives. , 2004, Biomaterials.

[29]  D. Haddleton,et al.  Sugar-Coated Amphiphilic Block Copolymer Micelles from Living Radical Polymerization: Recognition by Immobilized Lectins , 2003 .

[30]  W. Brittain,et al.  Polymer brushes: surface-immobilized macromolecules , 2000 .

[31]  Scott T. Milner,et al.  Theory of the grafted polymer brush , 1988 .