Influence of the molecular design on the antifouling performance of poly(ethylene glycol) monolayers grafted on (111) Si

Langmuir

Volumn 28, Issue 41, 2012, Pages 14654-14664

  Perez, Emmanuel ^a   Lahlil, Khalid ^a   Rougeau, Cyrille ^a   Moraillon, Anne ^a   Chazalviel, Jean Noël ^a   Ozanam, François ^a   Gouget Laemmel, Anne Chantal ^a  

^a LABORATOIRE DE PHYSIQUE DE LA MATIÈRE CONDENSÉE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AFM IMAGING; ANTIFOULING; BSA ADSORPTION; ETHYLENE OXIDES; GRAFTED CHAINS; GRAFTED LAYERS; HIGH RESISTANCE; HYDROGENATED SILICON; MOLECULAR DESIGN; MONOMETHYL ETHERS; OLIGOETHYLENE OXIDE; SURFACE CONCENTRATION;

ADSORPTION; ETHERS; GOLD; MONOLAYERS; POLYETHYLENE GLYCOLS; SILICON;

GRAFTING (CHEMICAL);

BOVINE SERUM ALBUMIN; MACROGOL DERIVATIVE; SILICON;

ADSORPTION; ANIMAL; ARTICLE; BIOFOULING; CATTLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; SURFACE PROPERTY;

ADSORPTION; ANIMALS; BIOFOULING; CATTLE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; SERUM ALBUMIN, BOVINE; SILICON; SURFACE PROPERTIES;

EID: 84867515498     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la303022a     Document Type: Article

References (54)

1. Harris, J. M. Poly(ethylene glycol) chemistry: Biotechnical and Biomedical Applications; Plenum: New York, 1992.
2. Palegrosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. Formation on self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)META-OH on gold J. Am. Chem. Soc. 1991, 113 (1) 12-20
3. Charnley, M.; Textor, M.; Acikgoz, C. Designed polymer structures with antifouling-antimicrobial properties React. Funct. Polym. 2011, 71 (3) 329-334
4. Herrwerth, S.; Eck, W.; Reinhardt, S.; Grunze, M. Factors that determine the protein resistance of oligoether self-assembled monolayers-Internal hydrophilicity, terminal hydrophilicity, and lateral packing density J. Am. Chem. Soc. 2003, 125 (31) 9359-9366
5. Wyszogrodzka, M.; Haag, R. Study of Single Protein Adsorption onto Monoamino Oligoglycerol Derivatives: A Structure-Activity Relationship Langmuir 2009, 25 (10) 5703-5712
6. Li, L. Y.; Chen, S. F.; Zheng, J.; Ratner, B. D.; Jiang, S. Y. Protein adsorption on oligo(ethylene glycol)-terminated alkanethiolate self-assembled monolayers: The molecular basis for nonfouling behavior J. Phys. Chem. B 2005, 109 (7) 2934-2941
7. Zhu, B.; Eurell, T.; Gunawan, R.; Leckband, D. Chain-length dependence of the protein and cell resistance of oligo(ethylene glycol)-terminated self-assembled monolayers on gold J. Biomed. Mater. Res. 2001, 56 (3) 406-416
8. Wang, R. L. C.; Kreuzer, H. J.; Grunze, M. Molecular conformation and solvation of oligo(ethylene glycol)-terminated self-assembled monolayers and their resistance to protein adsorption J. Phys. Chem. B 1997, 101 (47) 9767-9773
9. Heuberger, M.; Drobek, T.; Voros, J. About the role of water in surface-grafted poly(ethylene glycol) layers Langmuir 2004, 20 (22) 9445-9448
10. Zheng, J.; Li, L. Y.; Chen, S. F.; Jiang, S. Y. Molecular simulation study of water interactions with oligo(ethylene glycol)-terminated alkanethiol self-assembled monolayers Langmuir 2004, 20 (20) 8931-8938
11. Wan, J. D.; Thomas, M. S.; Guthrie, S.; Vullev, V. I. Surface-Bound Proteins with Preserved Functionality Ann. Biomed. Eng. 2009, 37 (6) 1190-1205
12. Schlapak, R.; Pammer, P.; Armitage, D.; Zhu, R.; Hinterdorfer, P.; Vaupel, M.; Fruhwirth, T.; Howorka, S. Glass surfaces grafted with high-density poly(ethylene glycol) as substrates for DNA oligonucleotide microarrays Langmuir 2006, 22 (1) 277-285
13. Houseman, B. T.; Gawalt, E. S.; Mrksich, M. Maleimide-functionalized self-assembled monolayers for the preparation of peptide and carbohydrate biochips Langmuir 2003, 19 (5) 1522-1531
14. Harder, P.; Grunze, M.; Dahint, R.; Whitesides, G. M.; Laibinis, P. E. Molecular conformation in oligo(ethylene glycol)-terminated self-assembled monolayers on gold and silver surfaces determines their ability to resist protein adsorption J. Phys. Chem. B 1998, 102 (2) 426-436
15. Gnauck, M.; Jaehne, E.; Blaettler, T.; Tosatti, S.; Textor, M.; Adler, H. J. P. Carboxy-terminated oligo(ethylene glycol)-alkane phosphate: Synthesis and self-assembly on titanium oxide surfaces Langmuir 2007, 23 (2) 377-381
16. Wach, J. Y.; Malisova, B.; Bonazzi, S.; Tosatti, S.; Textor, M.; Zurcher, S.; Gademann, K. Protein-Resistant Surfaces through Mild Dopamine Surface Functionalization Chem.-Eur. J. 2008, 14 (34) 10579-10584
17. Parrish, B.; Breitenkamp, R. B.; Emrick, T. PEG- and peptide-grafted aliphatic polyesters by click chemistry J. Am. Chem. Soc. 2005, 127 (20) 7404-7410
18. Ma, C. F.; Hou, Y.; Liu, S.; Zhang, G. Z. Effect of Microphase Separation on the Protein Resistance of a Polymeric Surface Langmuir 2009, 25 (16) 9467-9472
19. Hong, R.; Fischer, N. O.; Verma, A.; Goodman, C. M.; Emrick, T.; Rotello, V. M. Control of protein structure and function through surface recognition by tailored nanoparticle scaffolds J. Am. Chem. Soc. 2004, 126 (3) 739-743
20. Hamers, R. J.; Butler, J. E.; Lasseter, T.; Nichols, B. M.; Russell, J. N.; Tse, K. Y.; Yang, W. S. Molecular and biomolecular monolayers on diamond as an interface to biology Diamond Relat. Mater. 2005, 14 (3-7) 661-668
21. Ostaci, R. V.; Damiron, D.; Capponi, S.; Vignaud, G.; Leger, L.; Grohens, Y.; Drockenmuller, E. Polymer brushes grafted to "Passivated" silicon substrates using click chemistry Langmuir 2008, 24 (6) 2732-2739
22. Ghosh, M.; Maiti, S.; Dutta, S.; Das, D.; Das, P. K. Covalently functionalized single-walled carbon nanotubes at reverse micellar interface: a strategy to improve lipase activity Langmuir 2012, 28 (3) 1715-24
23. Roman, J. A.; Niedzielko, T. L.; Haddon, R. C.; Parpura, V.; Floyd, C. L. Single-Walled Carbon Nanotubes Chemically Functionalized with Polyethylene Glycol Promote Tissue Repair in a Rat Model of Spinal Cord Injury J. Neurotrauma 2011, 28 (11) 2349-2362
24. Cicero, R. L.; Linford, M. R.; Chidsey, C. E. D. Photoreactivity of unsaturated compounds with hydrogen-terminated silicon(111) Langmuir 2000, 16 (13) 5688-5695
25. Faucheux, A.; Gouget-Laemmel, A. C.; Henry de Villeneuve, C.; Boukherroub, R.; Ozanam, F.; Allongue, P.; Chazalviel, J.-N. Well-defined carboxyl-terminated alkyl monolayers grafted onto H-Si(111): Packing density from a combined AFM and quantitative IR study Langmuir 2006, 22 (1) 153-162
26. Boukherroub, R. Chemical reactivity of hydrogen-terminated crystalline silicon surfaces Curr. Opin. Solid State Mater. Sci. 2005, 9 (1-2) 66-72
27. Ciampi, S.; Harper, J. B.; Gooding, J. J. Wet chemical routes to the assembly of organic monolayers on silicon surfaces via the formation of Si-C bonds: surface preparation, passivation and functionalization Chem. Soc. Rev. 2010, 39 (6) 2158-2183
28. Wayner, D. D. M.; Wolkow, R. A. Organic modification of hydrogen terminated silicon surfaces J. Chem. Soc., Perkin Trans. 2 2002, 1) 23-34
29. Jeyachandran, Y. L.; Mielezarski, E.; Rai, B.; Mielczarski, J. A. Quantitative and Qualitative Evaluation of Adsorption/Desorption of Bovine Serum Albumin on Hydrophilic and Hydrophobic Surfaces Langmuir 2009, 25 (19) 11614-11620
30. Kim, J.; Somorjai, G. A. Molecular packing of lysozyme, fibrinogen, and bovine serum albumin on hydrophilic and hydrophobic surfaces studied by infrared-visible sum frequency generation and fluorescence microscopy J. Am. Chem. Soc. 2003, 125 (10) 3150-3158
31. Munford, M. L.; Cortès, R.; Allongue, P. The preparation of ideally ordered flat H-Si(111) surfaces Sens. Mater. 2001, 13 (5) 259-269
32. Higashi, G. S.; Chabal, Y. J.; Trucks, G. W.; Raghavachari, K. Ideal hydrogen termination of the Si(111) surface App. Phys. Lett. 1990, 56 (7) 656-658
33. Boukherroub, R.; Morin, S.; Sharpe, P.; Wayner, D. D. M.; Allongue, P. Insights into the formation mechanisms of Si-OR monolayers from the thermal reactions of alcohols and aldehydes with Si(111)-H Langmuir 2000, 16 (19) 7429-7434
34. Wallart, X.; de Villeneuve, C. H.; Allongue, P. Truly quantitative XPS characterization of organic monolayers on silicon: Study of alkyl and alkoxy monolayers on H-Si(111) J. Am. Chem. Soc. 2005, 127 (21) 7871-7878
35. Sano, H.; Maeda, H.; Ichii, T.; Murase, K.; Noda, K.; Matsushige, K.; Sugimura, H. Alkyl and Alkoxyl Monolayers Directly Attached to Silicon: Chemical Durability in Aqueous Solutions Langmuir 2009, 25 (10) 5516-5525
36. Hacker, C. A.; Anderson, K. A.; Richter, L. J.; Richter, C. A. Comparison of Si-O-C interfacial bonding of alcohols and aldehydes on Si(111) formed from dilute solution with ultraviolet irradiation Langmuir 2005, 21 (3) 882-889
37. Zhong, Y. L.; Bernasek, S. L. Direct Photochemical Functionalization of Si(111) with Undecenol Langmuir 2011, 27 (5) 1796-1802
38. Zhu, X. Y.; Jun, Y.; Staarup, D. R.; Major, R. C.; Danielson, S.; Boiadjiev, V.; Gladfelter, W. L.; Bunker, B. C.; Guo, A. Grafting of high-density poly(ethylene glycol) monolayers on Si(111) Langmuir 2001, 17 (25) 7798-7803
39. Cecchet, F.; De Meersman, B.; Demoustier-Champagne, S.; Nysten, B.; Jonas, A. M. One step growth of protein antifouling surfaces: Monolayers of poly(ethylene oxide) (PEO) derivatives on oxidized and hydrogen-passivated silicon surfaces Langmuir 2006, 22 (3) 1173-1181
40. Lasseter, T. L.; Clare, B. H.; Abbott, N. L.; Hamers, R. J. Covalently modified silicon and diamond surfaces: Resistance to nonspecific protein adsorption and optimization for biosensing J. Am. Chem. Soc. 2004, 126 (33) 10220-10221
41. Zhong, Y. L.; Bernasek, S. L. Mild and Efficient Functionalization of Hydrogen-Terminated Si(111) via Sonochemical Activated Hydrosilylation J. Am. Chem. Soc. 2011, 133 (21) 8118-8121
42. Nuzzo, R. G.; Dubois, L. H.; Allara, D. L. Fundamental studies of microscopic wetting on organic surfaces 1. Formation and structural characterization of a self-consistent series of polyfunctional organic monolayers J. Am. Chem. Soc. 1990, 112 (2) 558-569
43. Sieval, A. B.; van den Hout, B.; Zuilhof, H.; Sudholter, E. J. R. Molecular modeling of covalently attached alkyl monolayers an the hydrogen-terminated Si(111) surface Langmuir 2001, 17 (7) 2172-2181
44. Moraillon, A.; Gouget-Laemmel, A. C.; Ozanam, F.; Chazalviel, J.-N. Amidation of monolayers on silicon in physiological buffers: A quantitative IR study J. Phys. Chem. C 2008, 112 (18) 7158-7167
45. Aureau, D.; Ozanam, F.; Allongue, P.; Chazalviel, J.-N. The titration of carboxyl-terminated monolayers revisited: In situ calibrated Fourier transform infrared study of well-defined monolayers on silicon Langmuir 2008, 24 (17) 9440-9448
46. Bocking, T.; Kilian, K. A.; Hanley, T.; Ilyas, S.; Gaus, K.; Gal, M.; Gooding, J. J. Formation of tetra(ethylene oxide) terminated Si-C linked monolayers and their derivatization with glycine: An example of a generic strategy for the immobilization of biomolecules on silicon Langmuir 2005, 21 (23) 10522-10529
47. Qin, G. T.; Zhang, R.; Makarenko, B.; Kumar, A.; Rabalais, W.; Romero, J. M. L.; Rico, R.; Cai, C. Z. Highly stable, protein resistant thin films on SiC-modified silicon substrates Chem. Commun. 2010, 46 (19) 3289-3291
48. Rosso, M.; Nguyen, A. T.; de Jong, E.; Baggerman, J.; Paulusse, J. M. J.; Giesbers, M.; Fokkink, R. G.; Norde, W.; Schroen, K.; van Rijn, C. J. M.; Zuilhof, H. Protein-Repellent Silicon Nitride Surfaces: UV-Induced Formation of Oligoethylene Oxide Mono layers ACS Appl. Mater. Interfaces 2011, 3 (3) 697-704
49. Clare, T. L.; Clare, B. H.; Nichols, B. M.; Abbott, N. L.; Hamers, R. J. Functional monolayers for improved resistance to protein adsorption: Oligo(ethylene glycol)-modified silicon and diamond surfaces Langmuir 2005, 21 (14) 6344-6355
50. Yam, C. M.; Lopez-Romero, J. M.; Gu, J. H.; Cai, C. Z. Protein-resistant monolayers prepared by hydrosilylation of alpha-oligo(ethylene glycol)-omega-alkenes on hydrogen-terminated silicon (111) surfaces Chem. Commun. 2004, 21, 2510-2511
51. Ozanam, F.; Chazalviel, J.-N. Insitu Infrared vibrational study of the early stages of silicon oxidation at the interface with a non-aqueous electrolyte J. Electroanal. Chem. 1989, 269 (2) 251-266
52. Yam, C. M.; Gu, J. H.; Li, S.; Cai, C. Z. Comparison of resistance to protein adsorption and stability of thin films derived from alpha-hepta- (ethylene glycol) methyl omega-undecenyl ether on H-Si(111) and H-Si(100) surfaces J. Colloid Interface Sci. 2005, 285 (2) 711-718
53. Kilian, K. A.; Bocking, T.; Gaus, K.; Gal, M.; Gooding, J. J. Si-C linked oligo(ethylene glycol) layers in silicon-based photonic crystals: Optimization for implantable optical materials Biomaterials 2007, 28 (20) 3055-3062
54. Gorostiza, P.; Henry de Villeneuve, C.; Sun, Q. Y.; Sanz, F.; Wallart, X.; Boukherroub, R.; Allongue, P. Water exclusion at the nanometer scale provides long-term passivation of silicon(111) grafted with alkyl monolayers J. Phys. Chem. B 2006, 110 (11) 5576-5585