Construction of a densely poly(ethylene glycol)-chain-tethered surface and its performance

Polymer Journal

Volumn 43, Issue 12, 2011, Pages 949-958

  Nagasaki, Yukio ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

antibody; biosensing; DNA; end functionalized poly(ethylene glycol); enzyme linked immunosorbent assay; hybrid biointerface; soft interface

Indexed keywords

ACTIVE ESTERS; BIO-MOLECULAR; BIOINTERFACES; BIOSENSING; CHAIN DENSITY; COIMMOBILIZATION; DNA IMMOBILIZATION; ENZYME LINKED IMMUNOSORBENT ASSAY; HYBRID SURFACE; IMMOBILIZED ANTIBODIES; IMMUNE RESPONSE; NON-BIOFOULING; NON-BIOFOULING SURFACES; NONFOULING; PROTEIN ADSORPTION; REDUCTIVE AMINATION; SUBSTRATE SURFACE; TETHERED CHAINS;

ADSORPTION; ALDEHYDES; ANTIBODIES; BIOFOULING; DNA; ETHYLENE; GLYCOLS; ORGANIC COMPOUNDS; POLYETHYLENE GLYCOLS;

SURFACES;

EID: 82955199956     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2011.93     Document Type: Review

References (85)

1. Schultz, J., Mrksich, M., Bhatia, S. N. & Brady, D. J. Biosensing: International Research and Development (Springer, Tokyo, 2006).
2. Edwards, R. Immunodiagnostics. Practical Approach (Practical Approach Series) (Oxford University Press, London, 1999).
3. Wild, D. G. (ed.). The Immunoassay Handbook 3rd edn (Elsevier, Amsterdam, 2005).
4. Kurien, B. T. & Hal Scofield, R. (ed.). Protein Blotting and Detection: Methods and Protocols (Methods in Molecular Biology) (Humana Press, New York, 2009).
5. Fung, E. Protein Arrays Methods and Protocols (Methods in Molecular Biology) (Humana Press, New York, 2010).
6. Hermanson, G. T. Bioconjugate Techniques 2nd edn (Academic Press, Waltham, 2008).
7. Becker, G. S., Copeland, C. W. & Lister, S. A. Mad Cow Disease Bovine Spongiform Encephalopathy (Nova Publishers, Hauppauge, 2008).
8. Mori, Y., Nagaoka, S., Takiuchi, H., Kikuchi, T., Noguchi, N., Tanzawa, H. & Noishiki, Y. A new antithrombogenic materials with long polyethylene oxide chain. Trans. Am. Soc. Artif. Intern. Organs 28, 459 (1982) Scheme 5: OligoDNA/poly(ethylene glycol) (PEG) hybridized surface (densely packed mix PEG chain improves not only non-fouling character but also orientation of oligoDNA). Figure 7: Surface plasmon resonance (SPR) sensing of complementary single-stranded DNA (ssDNA, red bar) and mismatched ssDNA (blue bar) on a probe ssDNA-sulfanyl (SH)-immobilized gold surface: (1) bare and (2) a poly(ethylene glycol) (PEG)/poly[2-(N,N-dimethylamino)ethyl methacrylate] (PAMA, 5k/5k)-modified surface. This figure is reproduced from Yoshimoto et al., 73 by courtesy of the publishers, Chemical Society of Japan. Scheme 6: Mixed-poly(ethylene glycol) (PEG) tethered-chain possessing freesulfanyl (SH) group at the PEG chain end on gold surface (PEG chain improves non-fouling character and prevents loop formation of the SH-end group on gold surface).
9. Jeon, S. I. & Andrade, J. D. Protein-surface interactions in the presence of polyethylene oxide: II. Effect of protein size. J. Colloid Interface Sci. 142, 159-166 (1991).
10. Gölander, C.-G., Herron, J. N., Lim, K., Claesson, P., Stenius, P. & Andrade, J. D. in Poly(Ethyleneglycol) Chemistry, Biotechnical and Biomedical Applications (ed. Harris, J. M.) 221-245 (Plenum, New York, 1992).
11. Lina, Y. S., Hlady, V. & Gölander, C.-G. Colloids and surfaces B. Biointerfaces 3, 49-62 (1994).
12. Pasche, S., Volrols, 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 109, 17545-17552 (2005).
13. Otsuka, H., Nagasaki, Y. & Kataoka, K. Surface characterization of functionalized polylactide through the coating with heterobifunctional poly(ethylene glycol)/polylactide block copolymers. Biomacromolecules 1, 39-48 (2000).
14. Uchida, K., Otsuka, H., Kaneko, M., Kataoka, K. & Nagasaki, Y. A reactive poly(-ethylene glycol) layer to achieve specific surface plasmon resonance sensing with a high S/N ratio: The substantial role of a short underbrushed peg layer in minimizing nonspecific adsorption. Anal. Chem. 77, 1075-1080 (2005).
15. Nagasaki, Y. Engineering of poly(ethylene glycol) chain-tethered surfaces to obtain high performance bionanoparticles. Sci. Technol. Adv. Mater. 11, 054505 (2010).
16. Yuan, X., Fabregat, D., Yoshimoto, K. & Nagasaki, Y. Design of highly functional antiferritin-immunolatex by hybridization of antiferritin/mixed-PEG polymers onto polystyrene submicroparticles. Biomaterials (Symp. Ser.) 1054, 243-258 (2010) (Chapter 13).
17. Harbers, G. M., Barber, T. A., Healy, K. E., Stile, R. A. & Sumner, D. R. in Biomimetic Materials and Design (eds Dillow, A. & Lowman, A.) 55-90 (Marcel Dekker, New York, 2002).
18. Goddarda, J. M. & Hotchkiss, J. H. Polymer surface modification for the attachment of bioactive compounds. Prog. Poly. Sci. 32, 698-725 (2007).
19. Yoshimoto, K., Ichino, M. & Nagasaki, Y. Inverted pattern formation of cell microarrays on poly(ethylene glycol) (PEG) gel patterned surface and construction of hepatocyte spheroids on unmodified PEG gel microdomains. Lab on a Chip 9, 1286-1289 (2009).
20. Kojima, R., Yoshimoto, K., Miyoshi, H. & Nagasaki, Y. Spheroid array of fetal mouse liver cells constructed on a PEG-gel micropatterned surface: Upregulation of hepatic functions by co-culture with nonparenchymal liver cells. Lab on a Chip 9, 1991-1993 (2009).
21. Leckband, D., Sheth, S. & Halperin, A. Grafted poly(ethylene oxide) brushes as nonfouling surface coatings. J. Biomater. Sci. Poly. Ed. 10, 1125-1147 (1999).
22. Paschalis Alexandridis, T. A. H. Poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer surfactants in aqueous solutions and at interfaces: Thermodynamics, structure, dynamics, and modeling. Colloids Surf. A: Physicochem. Eng. Aspects 96, 1-46 (1995).
23. Otsuka, H., Nagasaki, Y. & Kataoka, K. Characterization of aldehyde-PEG tethered surfaces: Influence of PEG chain length on the specific biorecognition. Langmuir 20, 11285-11287 (2004).
24. Youngblood, J. P., Andruzzi, A., Ober, C. K., Hexemer, A., Kramer, E. J., Callow, J. A., Finlay, J. A. & Callow, M. E. Coatings based on side-chain ether-linked poly(ethylene glycol) and fluorocarbon polymers for the control of marine biofouling. Biofouling 19 (Suppl), 91-98 (2003).
25. Elbert, D. L. & Hubbell, J. A. Self-assembly and steric stabilization at heterogeneous, biological surfaces using adsorbing block copolymers. Chem. Biol. 5, 177-183 (1998).
26. Miyamoto, D., Oishi, M., Kojima, K., Yoshimoto, K. & Ngasaki, Y. Completely dispersible PEGylated gold nanoparticles under physiological conditions: Modification of gold nanoparticles with precisely controlled PEG-b-polyamine. Langmuir 24, 5010-5017 (2008).
27. Yoshimoto, K., Nishio, M., Sugasawa, H. & Nagasaki, Y. Direct observation of adsorption induced inactivation of antibody fragments surrounded by mixed-peg layer on a gold surface. J. Am. Chem. Soc. 132, 7982-7989 (2010).
28. Ning-Ping Huang, J. V., De Paul, S. M., Textor, M. & Spencer, N. D. Biotin-derivatized poly(L-lysine)-g-poly(ethylene glycol): A novel polymeric interface for bioaffinity sensing. Langmuir 18, 220-230 (2002).
29. Bailey, F. E. J. V. K. Alkylene Oxides and Their Polymers (Marcel Dekker Inc., New York, 1990).
30. Gibson, M. Pharmaceutical Preformulation and Formulation: A Practical Guide from Candidate Drug Selection to Commercial Dosage Form (Drugs and the Pharmaceutical Sciences) (Informa Healthcare, London, 2009).
31. Hustedt, H., Johansson, G. & Tjerneld, F. Aqueous Two-Phase Separation Systems (Kluwer Academic Publishers, Dordrecht, Netherlands, 1990).
32. E Glass, J. Hydrophilic Polymers: Performance with Environmental Acceptance (American Chemistry Society, Washington, DC, 1996).
33. Deutscher, M. P. Guide to protein purification. Meth Enzymol 182, 646-659 (1990).
34. Sowers, A. E. Cell Fusion (Plenum Press, New York, NY, 1987).
35. Shalaby, S. W., McCormick, C. L. & Butler, G. B. (ed.). Water-Soluble, Polymers, Synthesis, Solution Properties, and Applications, ACS Symposium Series, Vol. 467 (American Chemical Society, 1991).
36. Sawhney, A. S., Chandrashekhar, P. P. & Hubbell, J. A. Interfacial photopolymerization of polyethylene glycol-based hydrogels upon alginate-poly(l-lysine) microcapsules for enhanced biocompatibility. Biomaterials 14, 1008-1016 (1993).
37. Efremova, N. V., Hung, Y., Peppas, N. A. & Leckband, D. E. Direct measurement of interactions between tethered polyethylene glycol chains and adsorbed mucin layers. Langmuir 18, 836-845 (2002).
38. Martin Malmsten, D. M. Interfacial behavior of 'new' poly(ethylene oxide)-containing copolymers. J. Biomater. Sci. Polym. Ed. 10, 1075-1087 (1999).
39. Blaettler, T. M., Marcus Textor, S. P. & Griesser, H. J. High salt stability and protein resistance of poly(L-lysine)-g-poly(ethylene glycol) copolymers covalently immobilized via aldehyde plasma polymer interlayers on inorganic and polymeric substrates. Langmuir 22, 5760-5769 (2006).
40. Chen, Y., Kang, E. T., Neoh, K. G., Wang, P. & Tan, P. K. L. Surface modification of polyaniline film by grafting of poly(ethylene glycol) for reduction in protein adsorption and platelet adhesion. Synthetic Met. 110, 47-55 (2000).
41. Tsujii, Y., Ejaz, M., Yamamoto, S., Ohno, K., Urayama, K. & Fukuda, T. in Structure and Properties of High-Density Polymer Brushes (eds Advincula, R. C., Brittain, W. J., Caster, K. C. & Rühe, J.) (Polymer Brushes, Wiley-VCH, Weinheim, 2004).
42. Sofia, S. J., Premnath, V. & Merrill, E. W. Poly(ethylene oxide) grafted to silicon surfaces: Grafting density and protein adsorption. Macromolecules 31, 5059-5070 (1998).
43. Raju Francis, A. M. S., Carino, S. R., Logan, J. L., Underhill, R. S., Angot, S., Taton, D., Gnanou, Y. & Duran, R. S. Aggregation and surface morphology of a poly(ethylene oxide)-block-polystyrene three-arm star polymer at the air/water interface studied by AFM. Macromolecules 35, 6483-6485 (2002).
44. Emoto, K., Michihiro, I., Nagasaki, Y. & Kataoka, K. Functionality of polymeric micelle hydrogels with organized three-dimensional architecture on surfaces. J. Am. Chem. Soc. 122, 2653-2654 (2000).
45. Uchida, K., Hoshino, Y., Tamura, A., Yoshimoto, K., Kojima, S., Yamashita, K., Yamanaka, I., Otsuka, H., Kataoka, K. & Nagasaki, Y. Creation of a mixed poly (ethylene glycol) tethered-chain surface for preventing the non-specific adsorption of proteins and peptides. Biointerphases 2, 126 (2007).
46. Otsuka, H., Akiyama, Y., Nagasaki, Y. & Kataoka, K. Quantitative and reversible lectininduced association of gold nanoparticles modified with a-lactosyl-o-mercaptopoly( ethylene glycol). J. Am. Chem. Soc. 123, 8226-8230 (2001).
47. Wuelfing, W. P., Gross, S. M., Miles, D. T. & Murray, R. W. Nanometer gold clusters protected by surface-bound monolayers of thiolated poly(ethylene glycol) polymer electrolyte. J. Am. Chem. Soc. 120, 12696-12697 (1998).
48. Bearinger, J. P., Terrettaz, S., MicheL, R., Tirelli, N., Vogel, H., Textor, M. & Hubbell, J. A. Chemisorbed poly(propylene sulphide)-based copolymers resist biomolecular interactions. Nat. Mater. 2, 259 (2003).
49. Cooper, E. & Leggett, G. J. Static secondary ion mass spectrometry studies of selfassembled monolayers: Influence of adsorbate chain length and terminal functional group on rates of photooxidation of alkanethiols on gold. Langmuir 14, 4795 (1998).
50. Castner, D. G., Hinds, K. & Grainger, D. W. X-ray photoelectron spectroscopy sulfur 2p study of organic thiol and disulfide binding interactions with gold surfaces. Langmuir 12, 5083 (1996).
51. Pong, B.-K., Lee, J.-Y. & Trout, B. L. First principles computational study for understanding the interactions between ssDNA and gold nanoparticles: Adsorption of methylamine on gold nanoparticulate surfaces. Langmuir 21, 11599 (2005).
52. Felice, R. D. & Selloni, A. First principles computational study for understanding the interactions between ssDNA and gold nanoparticles: Adsorption of methylamine on gold nanoparticulate surfaces. J. Chem. Phys. 120, 4906-4914 (2004).
53. Ishii, T., Otsuka, H., Kataoka, K. & Nagasaki, Y. Preparation of functionally PEGylated gold nanoparticles with narrow distribution through autoreduction of auric cation by a-biotinyl-PEG-block-[poly(2-(N,N- dimethylamino)ethyl methacrylate)]. Langmuir 20, 561-564 (2004).
54. Furusho, H., Kitano, K., Hamaguchi, S. & Nagasaki, Y. Preparation of stable waterdispersible pegylated gold nanoparticles assisted by nonequilibrium atmospheric pressure plasma jets. Chem. Mater. 21, 3526-3535 (2009).
55. Nagasaki, Y., Kobayashi, H., Katsuyama, Y., Jomura, T. & Sakura, T. Enhanced immunoresponse of antibody/mixed-PEG co-immobilized surface construction of high-performance immunomagnetic ELISA system. J. Colloid Interface Sci. 309, 524-530 (2007).
56. Xiaofei, Y., Yoshimoto, K. & Nagasaki, Y. High-performance immunolatex possessing a mixedpeg/antibody coimmobilized surface: Highly sensitive ferritin immunodiagnostics. Anal. Chem. 81, 1549-1556 (2009).
57. Soukka, T., Paukkunen, J., Harma, H., Lonnberg, S., Lindroos, H. & Lovgren, T. Supersensitive time-resolved immunofluorometric assay of free prostate-specific antigen with nanoparticle label technology. Clin. Chem. 47, 1269 (2001).
58. Langer, R. & Tirrell, D. A. Designing materials for biology and medicine. Nature 428, 487-492 (2004).
59. Cooper, M. A. & Singleton, V. T. A survey of the 2001 to 2005 quartz crystal microbalance biosensor literature: Applications of acoustic physics to the analysis of biomolecular interactions. J. Mol. Recognit. 20, 154-184 (2007).
60. Belosludtsev, Y., Iverson, B., Lemeshko, S., Eggers, R., Wiese, R., Lee, S., Powdrill, T. & Hogan, M. DNA microarrays based on noncovalent oligonucleotide attachment and hybridization in two dimensions. Anal. Biochem. 292, 250-256 (2001).
61. Petrovykh, D. Y., Kimura-Suda, H., Tarlov, M. J. & Whitman, L. J. Quantitative characterization of DNA films by X-ray photoelectron spectroscopy. Langmuir 20, 429-440 (2004).
62. Höök, F., Ray, A., Nordén, B. & Kasemo, B. Characterization of PNA and DNA immobilization and subsequent hybridization with DNA using acoustic-shear-wave attenuation measurements. Langmuir 17, 8305-8312 (2001).
63. Love, J. C., Estroff, L. A., Kriebel, J. K., Nuzzo, R. G. & Whitesides, G. M. Selfassembled monolayers of thiolates on metals as a form of nanotechnology. Chem. Rev. 105, 1103-1169 (2005).
64. Ulman, A. Formation and structure of self-assembled monolayers. Chem. Rev. 96, 1533-1554 (1996).
65. Prime, K. L. & Whitesides, G. M. Self-assembled organic monolayers: Model systems for studying adsorption of proteins at surfaces. Science 252, 1164-1167 (1991).
66. Gong, P., Lee, C.-Y., Gamble, L. J., Castner, D. G. & Grainger, D. W. Hybridization behavior of mixed DNA/alkylthiol monolayers on gold: Characterization by surface plasmon resonance and 32p radiometric assay. Anal. Chem. 78, 3326-3334 (2006).
67. Lee, C.-Y., Gong, P., Harbers, G. M., Grainger, D. W., Castner, D. G. & Gamble, L. J. Surface coverage and structure of mixed DNA/alkylthiol monolayers on gold: Characterization by XPS, NEXAFS, and fluorescence intensity measurements. Anal. Chem. 78, 3316-3325 (2006).
68. Levicky, R., Herne, T. M., Tarlov, M. J. & Satija, S. K. Using self-assembly to control the structure of DNA monolayers on gold: A neutron reflectivity study. J. Am. Chem. Soc. 120, 9787-9792 (1998).
69. Boozer, C., Chen, S. & Jiang, S. Controlling DNA orientation on mixed ssDNA/OEG SAMs. Langmuir 22, 4694-4698 (2006).
70. Herne, T. M. & Tarlov, M. J. J. Characterization of DNA probes immobilized on gold surfaces. Am. Chem. Soc. 119, 8916-8920 (1997).
71. Peterlinz, K. A., Georgiadis, R. M., Herne, T. M. & Tarlov, M. J. Observation of hybridization and dehybridization of thiol-tethered DNA using two-color surface plasmon resonance spectroscopy. J. Am. Chem. Soc. 119, 3401-3402 (1997).
72. Nagasaki, Y. Polyethylene glycol-b-polyamine stabilized bionanoparticles for nanodiagnostics and nanotherapy. Chem. Lett. 37, 564-569 (2008).
73. Yoshimoto, K., Matsumoto, S., Asakawa, R., Uchida, K. & Nagasaki, Y. Immobilization and hybridization behavior of DNA on poly(ethylene glycol)-block-poly[2-(N,Ndimethylamino) ethyl methacrylate]-modified gold surfaces. Chem. Lett. 36, 1444-1445 (2007).
74. Oishi, M., Nakaogami, J., Ishii, T. & Nagasaki, Y. Smart PEGylated gold nanoparticles for the cytoplasmic delivery of siRNA to induce enhanced gene silencing. Chem. Lett. 35, 1046-1047 (2006).
75. Xiaofei, Y., Fabregat, D., Yoshimoto, K. & Nagasaki, Y. Efficient inhibition of interfacial nonspecific interaction to create practically utilizable high ferritin-response immunolatex. Anal. Chem. 81, 10097-10105 (2009).
76. Kubota, M., Yoshimoto, K., Xiaofei, Y. & Nagasaki, Y. Improvement of the thermal stability of streptavidin immobilized on magnetic beads by the construction of a mixed poly(ethylene glycol) tethered-chain layer. Polymer J. 43, 493-496 (2011).
77. Sakata, T., Maruyama, S., Ueda, A., Otsuka, H. & Miyahara, Y. Stable immobilization of an oligonucleotide probe on a gold substrate using tripodal thiol derivatives. Langmuir 23, 2269-2272 (2007).
78. Bearinger, J. P., Terrettaz, S., Michel, R., Tirelli, N., Vogel, H., Textor, M. & Hubbell, J. A. Chemisorbed poly(propylene sulphide)-based copolymers resist biomolecular interactions. Nat. Mater. 2, 259-264 (2003).
79. Feller, L. M., Cerritelli, S., Textor, M., Hubbell, J. A. & Tosatti, S. G. P. Influence of poly(propylene sulfide-block-ethylene glycol) di-and triblock copolymer architecture on the formation of molecular adlayers on gold surfaces and their effect on protein resistance: A candidate for surface modification in biosensor research. Macromolecules 38, 10503-10510 (2005).
80. Yoshimoto, K., Nozawa, M., Matsumoto, S., Echigo, T., Nemoto, S., Hatta, T. & Nagasaki, Y. Studies on the adsorption property and structure of polyamine-ended poly(ethylene glycol) derivatives on a gold surface by surface plasmon resonance and angle-resolved X-ray photoelectron spectroscopy. Langmuir 25, 12243-12249 (2009).
81. Konradi, R., Pidhatika, B., Mhlebach, A. & Textor, M. Poly-2-methyl-2-oxazoline: A peptide-like polymer for protein-repellent surfaces. Langmuir 24, 613-616 (2008).
82. Lee, S. & Spencer, N. D. Adsorption properties of poly(L-lysine)-graft-poly(ethylene glycol) (PLL-g-PEG) at a hydrophobic interface: Influence of tribological stress, pH, salt concentration, and polymer molecular weight. Langmuir 24, 9479-9488 (2008).
83. Nagasaki, Y., Yasugi, K., Kurokawa, K. & Iijima, M. Thermal-and dispersion-stable lipaseinstalled gold colloid: PEGylation of enzyme-installed gold colloid. Colloid Polymer Sci. 285, 563-567 (2007).
84. Xiaofei, Y., Iijima, M., Oishi, M. & Nagasaki, Y. Structure and activity assay of nanozymes prepared by the coimmobilization of practically useful enzymes and hydrophilic block copolymers on gold nanoparticles. Langmuir 24, 6903-6909 (2008).
85. Yoshimoto, K., Hirase, T., Nemoto, S., Hatta, T. & Nagasaki, Y. Facile construction of sulfanyl-terminated poly(ethylene glycol)-brushed layer on a gold surface for protein immobilization by the combined use of sulfanyl-ended telechelic and semitelechelic poly(ethylene glycol)s. Langmuir 24, 9623-9629 (2008).