Protein, cell and bacterial fouling resistance of polypeptoid-modified surfaces: effect of side-chain chemistry.

Peptidomimetic polymers consisting of poly-N-substituted glycine oligomers (polypeptoids) conjugated to biomimetic adhesive polypeptides were investigated as antifouling surface coatings. The polymers were immobilized onto TiO(2) surfaces via an anchoring peptide consisting of alternating residues of 3,4-dihydroxyphenylalanine (DOPA) and lysine. Three polypeptoid side-chain compositions were investigated for antifouling performance and stability toward enzymatic degradation. Ellipsometry and XPS analysis confirmed that purified polymers adsorbed strongly to TiO(2) surfaces, and the immobilized polymers were resistant to enzymatic degradation as demonstrated by mass spectrometry. All polypeptoid-modified surfaces exhibited significant reductions in adsorption of lysozyme, fibrinogen and serum proteins, and were resistant to 3T3 fibroblast cell attachment for up to seven days. Long-term in vitro cell attachment studies conducted for six weeks revealed the importance of polypeptoid side-chain composition, with a methoxyethyl side chain providing superior long-term fouling resistance compared to hydroxyethyl and hydroxypropyl side chains. Finally, attachment of both gram-positive and gram-negative bacteria for up to four days under continuous-flow conditions was significantly reduced on the polypeptoid-modified surfaces compared to unmodified TiO(2) surfaces. The results reveal the influence of polypeptoid side-chain chemistry on short-term and long-term protein, cell and bacterial fouling resistance.

[1]  K. Kataoka,et al.  Density control of poly(ethylene glycol) layer to regulate cellular attachment. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[2]  Shaoyi Jiang,et al.  Superlow fouling sulfobetaine and carboxybetaine polymers on glass slides. , 2006, Langmuir : the ACS journal of surfaces and colloids.

[3]  Norbert F Scherer,et al.  Single-molecule mechanics of mussel adhesion , 2006, Proceedings of the National Academy of Sciences.

[4]  P. Messersmith,et al.  Cell fouling resistance of polymer brushes grafted from ti substrates by surface-initiated polymerization: effect of ethylene glycol side chain length. , 2006, Biomacromolecules.

[5]  Shaoyi Jiang,et al.  Strong resistance of phosphorylcholine self-assembled monolayers to protein adsorption: insights into nonfouling properties of zwitterionic materials. , 2005, Journal of the American Chemical Society.

[6]  J. Satulovsky,et al.  Kinetics of protein adsorption and desorption on surfaces with grafted polymers. , 2005, Biophysical journal.

[7]  E. Wickstrom,et al.  Vancomycin covalently bonded to titanium beads kills Staphylococcus aureus. , 2005, Chemistry & biology.

[8]  M. Textor,et al.  Effects of ionic strength and surface charge on protein adsorption at PEGylated surfaces. , 2005, The journal of physical chemistry. B.

[9]  C. Ober,et al.  Self-assembled monolayers and polymer brushes in biotechnology: current applications and future perspectives. , 2005, Biomacromolecules.

[10]  C. McCormick,et al.  Direct, controlled synthesis of the nonimmunogenic, hydrophilic polymer, poly(N-(2-hydroxypropyl)methacrylamide) via RAFT in aqueous media. , 2005, Biomacromolecules.

[11]  P. Messersmith,et al.  Protein resistance of titanium oxide surfaces modified by biologically inspired mPEG-DOPA. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[12]  Hongwei Ma,et al.  Surface engineering strategies for control of protein and cell interactions , 2004 .

[13]  Jinho Hyun,et al.  “Non‐Fouling” Oligo(ethylene glycol)‐ Functionalized Polymer Brushes Synthesized by Surface‐Initiated Atom Transfer Radical Polymerization , 2004 .

[14]  Henny C van der Mei,et al.  Inhibition of adhesion of yeasts and bacteria by poly(ethylene oxide)-brushes on glass in a parallel plate flow chamber. , 2003, Microbiology.

[15]  Marcus Textor,et al.  Poly(l-lysine)-graft-poly(ethylene glycol) Assembled Monolayers on Niobium Oxide Surfaces: A Quantitative Study of the Influence of Polymer Interfacial Architecture on Resistance to Protein Adsorption by ToF-SIMS and in Situ OWLS , 2003 .

[16]  Jiang Wei,et al.  Covalent Attachment of Poly(ethylene glycol) to Surfaces, Critical for Reducing Bacterial Adhesion , 2003 .

[17]  Ralph G Nuzzo,et al.  Stable antifouling surfaces , 2003, Nature materials.

[18]  J. Hubbell,et al.  Chemisorbed poly(propylene sulphide)-based copolymers resist biomolecular interactions , 2003, Nature materials.

[19]  Bruce P. Lee,et al.  Mussel adhesive protein mimetic polymers for the preparation of nonfouling surfaces. , 2003, Journal of the American Chemical Society.

[20]  Annelise E Barron,et al.  Mimicry of bioactive peptides via non-natural, sequence-specific peptidomimetic oligomers. , 2002, Current opinion in chemical biology.

[21]  M. Textor,et al.  Optical grating coupler biosensors. , 2002, Biomaterials.

[22]  Helmut Thissen,et al.  Effects of cloud-point grafting, chain length, and density of PEG layers on competitive adsorption of ocular proteins. , 2002, Biomaterials.

[23]  D. Grainger,et al.  Functionalized poly(ethylene glycol)-grafted polysiloxane monolayers for control of protein binding , 2002 .

[24]  Marcus Textor,et al.  A comparative study of protein adsorption on titanium oxide surfaces using in situ ellipsometry, optical waveguide lightmode spectroscopy, and quartz crystal microbalance/dissipation , 2002 .

[25]  H. C. van der Mei,et al.  Bacterial adhesion to surface hydrophilic and hydrophobic contact lenses. , 2001, Biomaterials.

[26]  G. Whitesides,et al.  A Survey of Structure−Property Relationships of Surfaces that Resist the Adsorption of Protein , 2001 .

[27]  D. Branch,et al.  Long-term stability of grafted polyethylene glycol surfaces for use with microstamped substrates in neuronal cell culture. , 2001, Biomaterials.

[28]  J. Waite,et al.  Polyphosphoprotein from the adhesive pads of Mytilus edulis. , 2001, Biochemistry.

[29]  George M. Whitesides,et al.  Polymeric Thin Films That Resist the Adsorption of Proteins and the Adhesion of Bacteria , 2001 .

[30]  Marcus Textor,et al.  Titanium in Medicine : material science, surface science, engineering, biological responses and medical applications , 2001 .

[31]  M. Millar,et al.  Use of a continuous culture system linked to a modified Robbins device or flow cell to study attachment of bacteria to surfaces. , 2001, Methods in enzymology.

[32]  Milan Mrksich,et al.  Self-assembled monolayers of alkanethiolates presenting mannitol groups are inert to protein adsorption and cell attachment , 2000 .

[33]  Wisniewski,et al.  Methods for reducing biosensor membrane biofouling. , 2000, Colloids and surfaces. B, Biointerfaces.

[34]  J. Hubbell,et al.  Poly(l-lysine)-g-Poly(ethylene glycol) Layers on Metal Oxide Surfaces: Attachment Mechanism and Effects of Polymer Architecture on Resistance to Protein Adsorption† , 2000 .

[35]  J. Brash.  Exploiting the current paradigm of blood–material interactions for the rational design of blood-compatible materials , 2000, Journal of biomaterials science. Polymer edition.

[36]  M Morra,et al.  On the molecular basis of fouling resistance , 2000, Journal of biomaterials science. Polymer edition.

[37]  P. E. Laibinis,et al.  Protein-resistant coatings for glass and metal oxide surfaces derived from oligo(ethylene glycol)-terminated alkytrichlorosilanes. , 1998, Biomaterials.

[38]  M. Textor,et al.  Plasma protein adsorption on titanium: comparative in situ studies using optical waveguide lightmode spectroscopy and ellipsometry , 1998 .

[39]  Y. Qiu,et al.  Biomimetic engineering of non-adhesive glycocalyx-like surfaces using oligosaccharide surfactant polymers , 1998, Nature.

[40]  Spectroscopic ellipsometry for polymer thin films , 1998 .

[41]  S. Hubchak,et al.  P(AAm-co-EG) Interpenetrating Polymer Networks Grafted to Oxide Surfaces: Surface Characterization, Protein Adsorption, and Cell Detachment Studies , 1997 .

[42]  Samuel Zalipsky,et al.  Poly(ethylene glycol): Chemistry and Biological Applications , 1997 .

[43]  G M Whitesides,et al.  Using self-assembled monolayers to understand the interactions of man-made surfaces with proteins and cells. , 1996, Annual review of biophysics and biomolecular structure.

[44]  K. Ishihara,et al.  Synthesis of phospholipid polymers having a urethane bond in the side chain as coating material on segmented polyurethane and their platelet adhesion-resistant properties. , 1995, Biomaterials.

[45]  Walter H. Moos,et al.  Comparison of the proteolytic susceptibilities of homologous L‐amino acid, D‐amino acid, and N‐substituted glycine peptide and peptoid oligomers , 1995 .

[46]  D C Spellmeyer,et al.  Discovery of nanomolar ligands for 7-transmembrane G-protein-coupled receptors from a diverse N-(substituted)glycine peptoid library. , 1994, Journal of medicinal chemistry.

[47]  J. Bryers.  Biofilms and the technological implications of microbial cell adhesion , 1994 .

[48]  G. Whitesides,et al.  Adsorption of proteins onto surfaces containing end-attached oligo(ethylene oxide): a model system using self-assembled monolayers , 1993 .

[49]  Thomas A. Horbett,et al.  Chapter 13 Principles underlying the role of adsorbed plasma proteins in blood interactions with foreign materials , 1993 .

[50]  B. Ratner.  The blood compatibility catastrophe. , 1993, Journal of biomedical materials research.

[51]  Stephen B. H. Kent,et al.  Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis , 1992 .

[52]  G. Whitesides,et al.  Self-assembled organic monolayers: model systems for studying adsorption of proteins at surfaces , 1991, Science.

[53]  J. Waite,et al.  Polyphenolic Substance of Mytilus edulis: Novel Adhesive Containing L-Dopa and Hydroxyproline. , 1981, Science.

[54]  F. Veer,et al.  Ellipsometry as a tool to study the adsorption behavior of synthetic and biopolymers at the air–water interface , 1978 .

[55]  J. H. Scofield,et al.  Hartree-Slater subshell photoionization cross-sections at 1254 and 1487 eV , 1976 .