Surface-grafted polysarcosine as a peptoid antifouling polymer brush

Langmuir

Volumn 28, Issue 46, 2012, Pages 16099-16107

  Lau, King Hang Aaron ^a,b   Ren, Chunlai ^d   Sileika, Tadas S ^a,b   Park, Sung Hyun ^a,b   Szleifer, Igal ^a,b,c   Messersmith, Phillip B ^a,b,c  

^a Northwestern University   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c NORTHWESTERN UNIVERSITY   (United States)

^d NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFOULING; ANTIFOULING POLYMERS; BACTERIAL STRAINS; CELL ATTACHMENTS; CRITICAL CHAIN; FIBROBLAST CELLS; GRAFTED CHAINS; MOLECULAR THEORY; N-CARBOXYANHYDRIDE; NON-SPECIFIC PROTEIN ADSORPTION; PEPTIDOMIMETICS; PEPTOIDS; POLYSARCOSINE; PROTEIN ADSORPTION; PROTEOLYTIC DEGRADATION; SARCOSINE; SIDE-CHAINS; SURFACE CHAIN DENSITY; WATER CONTACT ANGLE MEASUREMENT;

AMINO ACIDS; CELL CULTURE; CHAIN LENGTH; HIGH PRESSURE LIQUID CHROMATOGRAPHY;

GRAFTING (CHEMICAL);

ADHESIVE PROTEIN, MUSSEL; DRUG DERIVATIVE; PEPTIDE; PEPTOID; POLYSARCOSINE; PROTEIN; SARCOSINE;

ADSORPTION; ANIMAL; ARTICLE; BACTERIUM ADHERENCE; CELL ADHESION; CELL STRAIN 3T3; CHEMISTRY; CYTOLOGY; ESCHERICHIA COLI; FIBROBLAST; MATERIALS TESTING; METHODOLOGY; MOUSE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

3T3 CELLS; ADSORPTION; ANIMALS; BACTERIAL ADHESION; CELL ADHESION; ESCHERICHIA COLI; FIBROBLASTS; MATERIALS TESTING; MICE; PEPTIDES; PEPTOIDS; PROTEINS; PSEUDOMONAS AERUGINOSA; SARCOSINE; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PROPERTIES;

EID: 84869419568     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la302131n     Document Type: Article

References (72)

1. Sapatnekar, S.; Kieswetter, K. M.; Merritt, K.; Anderson, J. M.; Cahalan, L.; Verhoeven, M.; Hendriks, M.; Fouache, B.; Cahalan, P. Blood biomaterial interactions in a flow system in the presence of bacteria - Effect of protein adsorption J. Biomed. Mater. Res. 1995, 29, 247-256
2. Ostuni, E.; Chapman, R. G.; Holmlin, R. E.; Takayama, S.; Whitesides, G. M. A survey of structure-property relationships of surfaces that resist the adsorption of protein Langmuir 2001, 17, 5605-5620
3. Kwak, D.; Wu, Y.; Horbett, T. A. Fibrinogen and von Willebrand's factor adsorption are both required for platelet adhesion from sheared suspensions to polyethylene preadsorbed with blood plasma J. Biomed. Mater. Res., Part A 2005, 74A, 69-83
4. Arima, Y.; Kawagoe, M.; Toda, M.; Iwata, H. Complement activation by polymers carrying hydroxyl groups ACS Appl. Mater. Interfaces 2009, 1, 2400-2407
5. Vogler, E. A.; Siedlecki, C. A. Contact activation of blood-plasma coagulation Biomaterials 2009, 30, 1857-1869
6. Nonckreman, C. J.; Fleith, S.; Rouxhet, P. G.; Dupont-Gillain, C. C. Competitive adsorption of fibrinogen and albumin and blood platelet adhesion on surfaces modified with nanoparticles and/or PEO Colloids Surf., B 2010, 77, 139-149
7. Zilla, P.; Bezuidenhout, D.; Human, P. Prosthetic vascular grafts: Wrong models, wrong questions and no healing Biomaterials 2007, 28, 5009-5027
8. Jordan, S. W.; Chaikof, E. L. Novel thromboresistant materials J. Vasc. Surg. 2007, 45, 104A-115A
9. Venkatraman, S.; Boey, F.; Lao, L. L. Implanted cardiovascular polymers: Natural, synthetic and bio-inspired Prog. Polym. Sci. 2008, 33, 853-874
10. Ratner, B. A perspective on titanium biocompatibility. In Titanium in Medicine: Material Science, Surface Science, Engineering, Biological Responses and Medical Applications; Brunette, D. M.; Tengvall, P.; Thomsen, P.; Textor, M., Eds.; Springer: Berlin and Heidelberg, 2000; pp 1-12.
11. Anderson, J. M. Biological responses to materials Annu. Rev. Mater. Res. 2001, 31, 81-110
12. Weinstein, R. A.; Gaynes, R.; Edwards, J. R.; System, N. N. I. S. Overview of nosocomial infections caused by Gram-negative bacilli Clin. Infect. Dis. 2005, 41, 848-854
13. Ziebuhr, W.; Hennig, S.; Eckart, M.; Kränzler, H.; Batzilla, C.; Kozitskaya, S. Nosocomial infections by Staphylococcus epidermidis: how a commensal bacterium turns into a pathogen Int. J. Antimicrob. Agents 2006, 28, 14-20
14. Kuijer, R.; Jansen, E. J. P.; Emans, P. J.; Bulstra, S. K.; Riesle, J.; Pieper, J.; Grainger, D. W.; Busscher, H. J. Assessing infection risk in implanted tissue-engineered devices Biomaterials 2007, 28, 5148-5154
15. Walkey, C. D.; Chan, W. C. W. Understanding and controlling the interaction of nanomaterials with proteins in a physiological environment Chem. Soc. Rev. 2012, 41, 2780-2799
16. Rastogi, A.; Nad, S.; Tanaka, M.; Mota, N. D.; Tague, M.; Baird, B. A.; Abrunifa, H. c. D.; Ober, C. K. Preventing nonspecific adsorption on polymer brush covered gold electrodes using a modified ATRP initiator Biomacromolecules 2009, 10, 2750-2758
17. Eglin, D.; Mortisen, D.; Alini, M. Degradation of synthetic polymeric scaffolds for bone and cartilage tissue repairs Soft Matter 2009, 5, 938-947
18. Chelmowski, R.; Köster, S. D.; Kerstan, A.; Prekelt, A.; Grunwald, C.; Winkler, T.; Metzler-Nolte, N.; Terfort, A.; Wöll, C. Peptide-based SAMs that resist the adsorption of proteins J. Am. Chem. Soc. 2008, 130, 14952-14953
19. Kanoatov, M.; Krylov, S. N. DNA adsorption to the reservoir walls causing irreproducibility in studies of protein-DNA interactions by methods of kinetic capillary electrophoresis Anal. Chem. 2011, 83, 8041-8045
20. Le, N. C. H.; Gubala, V.; Gandhiraman, R. P.; Daniels, S.; Williams, D. E. Evaluation of different nonspecific binding blocking agents deposited inside poly(methyl methacrylate) microfluidic flow-cells Langmuir 2011, 27, 9043-9051
21. Simon, R. J.; Kania, R. S.; Zuckermann, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D. C.; Tan, R. Y.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Peptoids - A modular approach to drug discovery Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 9367-9371
22. Kodadek, T.; Reddy, M. M.; Olivos, H. J.; Bachhawat-Sikder, K.; Alluri, P. G. Synthetic molecules as antibody replacements Acc. Chem. Res. 2004, 37, 711-718
23. Horne, W. S. Peptide and peptoid foldamers in medicinal chemistry Expert Opin. Drug Discovery 2011, 6, 1247-1262
24. Miller, S. M.; Simon, R. J.; Ng, S.; Zuckermann, R. N.; Kerr, J. M.; Moos, W. H. Comparison of the proteolytic susceptibilities of homologous L-amino acids, D-amino-acid, and N-substituted glycine peptide and peptoid oligomers Drug Dev. Res. 1995, 35, 20-32
25. Sui, Q.; Borchardt, D.; Rabenstein, D. L. Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids J. Am. Chem. Soc. 2007, 129, 12042-12048
26. Szleifer, I. Protein adsorption on surfaces with grafted polymers: A theoretical approach Biophys. J. 1997, 72, 595-612
27. Halperin, A. Polymer brushes that resist adsorption of model proteins - Design parameters Langmuir 1999, 15, 2525-2533
28. Fang, F.; Satulovsky, J.; Szleifer, I. Kinetics of protein adsorption and desorption on surfaces with grafted polymers Biophys. J. 2005, 89, 1516-1533
29. McPherson, T.; Kidane, A.; Szleifer, I.; Park, K. Prevention of protein adsorption by tethered poly(ethylene oxide) layers: Experiments and single-chain mean-field analysis Langmuir 1998, 14, 176-186
30. Kingshott, P.; Thissen, H.; Griesser, H. J. Effects of cloud-point grafting, chain length, and density of PEG layers on competitive adsorption of ocular proteins Biomaterials 2002, 23, 2043-2056
31. Pasche, S.; Vörös, J.; Griesser, H. J.; Spencer, N. D.; Textor, M. Effects of ionic strength and surface charge on protein adsorption at PEGylated surfaces J. Phys. Chem. B 2005, 109, 17545-17552
32. Nakaya, T.; Li, Y.-J. Phospholipid polymers Prog. Polym. Sci. 1999, 24, 143-181
33. West, S. L.; Salvage, J. P.; Lobb, E. J.; Armes, S. P.; Billingham, N. C.; Lewis, A. L.; Hanlon, G. W.; Lloyd, A. W. The biocompatibility of crosslinkable copolymer coatings containing sulfobetaines and phosphobetaines Biomaterials 2004, 25, 1195-1204
34. Zhang, Z.; Zhang, M.; Chen, S.; Horbett, T. A.; Ratner, B. D.; Jiang, S. Blood compatibility of surfaces with superlow protein adsorption Biomaterials 2008, 29, 4285-4291
35. Estephan, Z. G.; Schlenoff, P. S.; Schlenoff, J. B. Zwitteration as an alternative to PEGylation Langmuir 2011, 27, 6794-6800
36. Toomey, R.; Tirrell, M. Functional polymer brushes in aqueous media from self-assembled and surface-initiated polymers Annu. Rev. Phys. Chem. 2008, 59, 493-517
37. Ayres, N. Polymer brushes: Applications in biomaterials and nanotechnology Polym. Chem. 2010, 1, 769-777
38. Feng, W.; Gao, X.; McClung, G.; Zhu, S. P.; Ishihara, K.; Brash, J. L. Methacrylate polymer layers bearing poly(ethylene oxide) and phosphorylcholine side chains as non-fouling surfaces: In vitro interactions with plasma proteins and platelets Acta Biomater. 2011, 7, 3692-3699
39. Lin, S.; Zhang, B.; Skoumal, M. J.; Ramunno, B.; Li, X.; Wesdemiotis, C.; Liu, L.; Jia, L. Antifouling poly(β-peptoid)s Biomacromolecules 2011, 12, 2573-2582
40. Statz, A. R.; Meagher, R. J.; Barron, A. E.; Messersmith, P. B. New peptidomimetic polymers for antifouling surfaces J. Am. Chem. Soc. 2005, 127, 7972-7973
41. Statz, A. R.; Park, J. P.; Chongsiriwatana, N. P.; Barron, A. E.; Messersmith, P. B. Surface-immobilised antimicrobial peptoids Biofouling 2008, 24, 439-448
42. Statz, A. R.; Kuang, J. H.; Ren, C. L.; Barron, A. E.; Szleifer, I.; Messersmith, P. B. Experimental and theoretical investigation of chain length and surface coverage on fouling of surface grafted polypeptoids Biointerphases 2009, 4, FA22-FA32
43. Lau, K. H. A.; Ren, C.; Park, S. H.; Szleifer, I.; Messersmith, P. B. An experimental-theoretical analysis of protein adsorption on peptidomimetic polymer brushes Langmuir 2012, 28, 2288-2298
44. Douy, A.; Gallot, B. Amphipathic block copolymers with two polypeptide blocks: Synthesis and structural study of poly(Nε-trifluoroacetyl-l-lysine) -polysarcosine copolymers Polymer 1987, 28, 147-154
45. Fetsch, C.; Grossmann, A.; Holz, L.; Nawroth, J. F.; Luxenhofer, R. Polypeptoids from N-substituted glycine N-carboxyanhydrides: Hydrophilic, hydrophobic, and amphiphilic polymers with Poisson distribution Macromolecules 2011, 44, 6746-6758
46. Tang, Y. C.; Deber, C. M. Hydrophobicity and helicity of membrane-interactive peptides containing peptoid residues Biopolymers 2002, 65, 254-262
47. Bovey, F. A.; Ryan, J. J.; Hood, F. P. Polymer nuclear magnetic resonance spectroscopy. XV. The conformation of polysarcosine Macromolecules 1968, 1, 305-307
48. Mattice, W. L. Comparison of conformational map for poly(L-proline) with conformational maps for polysarcosine and poly(N-methyl-L-alanine) Macromolecules 1973, 6, 855-858
49. Sisido, M.; Imanishi, Y.; Higashimura, T. Static and dynamic studies on the end-to-end intrachain energy transfer on a polysarcosine chain Macromolecules 1979, 12, 975-980
50. Butterfoss, G. L.; Renfrew, P. D.; Kuhlman, B.; Kirshenbaum, K.; Bonneau, R. A preliminary survey of the peptoid folding landscape J. Am. Chem. Soc. 2009, 131, 16798-16807
51. Ostuni, E.; Chapman, R. G.; Liang, M. N.; Meluleni, G.; Pier, G.; Ingber, D. E.; Whitesides, G. M. Self-assembled monolayers that resist the adsorption of proteins and the adhesion of bacterial and mammalian cells Langmuir 2001, 17, 6336-6343
52. Chan, W. C.; White, P. D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Oxford University Press: New York, 2000.
53. Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis J. Am. Chem. Soc. 1992, 114, 10646-10647
54. Wertz, C. F.; Santore, M. M. Fibrinogen adsorption on hydrophilic and hydrophobic surfaces: Geometrical and energetic aspects of interfacial relaxations Langmuir 2002, 18, 706-715
55. Clark, A. J.; Kotlicki, A.; Haynes, C. A.; Whitehead, L. A. A new model of protein adsorption kinetics derived from simultaneous measurement of mass loading and changes in surface energy Langmuir 2007, 23, 5591-5600
56. Li, L.; Chen, S.; Zheng, J.; Ratner, B. D.; Jiang, S. Protein adsorption on oligo(ethylene glycol)-terminated alkanethiolate self-assembled monolayers: The molecular basis for nonfouling behavior J. Phys. Chem. B 2005, 109, 2934-2941
57. Kenausis, G. L.; Vörös, J.; Elbert, D. L.; Huang, N.; Hofer, R.; Ruiz-Taylor, L.; Textor, M.; Hubbell, J. A.; Spencer, N. D. Poly(l-lysine)-g-poly(ethylene glycol) layers on metal oxide surfaces: Attachment mechanism and effects of polymer architecture on resistance to protein adsorption J. Phys. Chem. B 2000, 104, 3298-3309
58. Dalsin, J. L.; Lin, L.; Tosatti, S.; Vörös, J.; Textor, M.; Messersmith, P. B. Protein resistance of titanium oxide surfaces modified by biologically inspired mPEG-DOPA Langmuir 2004, 21, 640-646
59. Gillich, T.; Benetti, E. M.; Rakhmatullina, E.; Konradi, R.; Li, W.; Zhang, A.; Schlüter, A. D.; Textor, M. Self-assembly of focal point oligo-catechol ethylene glycol dendrons on titanium oxide surfaces: Adsorption kinetics, surface characterization, and nonfouling properties J. Am. Chem. Soc. 2011, 133, 10940-10950
60. Beurer, E.; Venkataraman, N. V.; Sommer, M.; Spencer, N. D. Protein and nanoparticle adsorption on orthogonal, charge-density-versus-net-charge surface-chemical gradients Langmuir 2012, 28, 3159-3166
61. Wang, I. W.; Anderson, J. M.; Jacobs, M. R.; Marchant, R. E. Adhesion of Staphylococcus epidermidis to biomedical polymers: Contributions of surface thermodynamics and hemodynamic shear conditions J. Biomed. Mater. Res. 1995, 29, 485-493
62. Fang; Szleifer, I. Effect of molecular structure on the adsorption of protein on surfaces with grafted polymers Langmuir 2002, 18, 5497-5510
63. Satulovsky, J.; Carignano, M. A.; Szleifer, I. Kinetic and thermodynamic control of protein adsorption Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9037-9041
64. Waite, H. J.; Tanzer, M. L. Polyphenolic substance of Mytilus edulis: Novel adhesive containing L-Dopa and hydroxyproline Science 1981, 212, 1038-1040
65. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-inspired surface chemistry for multifunctional coatings Science 2007, 318, 426-430
66. Ham, H. O.; Liu, Z.; Lau, K. H. A.; Lee, H.; Messersmith, P. B. Facile DNA immobilization on surfaces through a catecholamine polymer Angew. Chem., Int. Ed. 2011, 50, 732-736
67. Gorbet, M. B.; Sefton, M. V. M. V. Biomaterial-associated thrombosis: roles of coagulation factors, complement, platelets and leukocytes Biomaterials 2004, 25, 5681-5703
68. Saxer, S.; Portmann, C.; Tosatti, S.; Gademann, K.; Zuercher, S.; Textor, M. Surface assembly of catechol-functionalized poly(L-lysine)-graft- poly(ethylene glycol) copolymer on titanium exploiting combined electrostatically driven self-organization and blomimetic strong adhesion Macromolecules 2010, 43, 1050-1060
69. Pei, J.; Hall, H.; Spencer, N. D. The role of plasma proteins in cell adhesion to PEG surface-density-gradient-modified titanium oxide Biomaterials 2011, 32, 8968-8978
70. Sherertz, R. J.; Sarubbi, F. A. A three-year study of nosocomial infections associated with Pseudomonas aeruginosa J. Clin. Microbiol. 1983, 18, 160-164
71. Pierce, G. E. Pseudomonas aeruginosa, Candida albicans, and device-related nosocomial infections: implications, trends, and potential approaches for control J. Ind. Microbiol. Biotechnol. 2005, 32, 309-318
72. Kingshott, P.; Wei, J.; Bagge-Ravn, D.; Gadegaard, N.; Gram, L. Covalent attachment of poly(ethylene glycol) to surfaces, critical for reducing bacterial adhesion Langmuir 2003, 19, 6912-6921