Effects of composition of oligo(ethylene glycol)-based mixed monolayers on peptide grafting and human immunoglobulin detection

Journal of Physical Chemistry C

Volumn 118, Issue 10, 2014, Pages 5361-5373

  Islam, Nafisa ^a   Gurgel, Patrick V ^a   Rojas, Orlando J ^a,b   Carbonell, Ruben G ^a,c  

^a North Carolina State University   (United States)

^b AALTO UNIVERSITY   (Finland)

^c NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; ETHYLENE GLYCOL; GRAFTING (CHEMICAL); POLYOLS; SELF ASSEMBLED MONOLAYERS; SURFACE PLASMON RESONANCE;

BINDING CAPACITIES; CHINESE HAMSTER OVARY; DISSOCIATION CONSTANT; HUMAN IMMUNOGLOBULIN; HYDROXYL-TERMINATED; MIXED SELF ASSEMBLED MONOLAYERS; OLIGO(ETHYLENE GLYCOL); PRECURSOR SOLUTIONS;

PEPTIDES;

EID: 84896363901     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp411469u     Document Type: Article

References (67)

1. Putzbach, W.; Ronkainen, N. Immobilization Techniques in the Fabrication of Nanomaterial-Based Electrochemical Biosensors: A Review Sensors 2013, 13, 4811-4840
2. Jans, K.; Bonroy, K.; De Palma, R.; Reekmans, G.; Jans, H.; Laureyn, W.; Smet, M.; Borghs, G.; Maes, G. Stability of Mixed Peo Thiol Sams for Biosensing Applications Langmuir 2008, 24, 3949-3954
3. Witt, D.; Klajn, R.; Barski, P.; Grzybowski, B. A. Applications, Properties and Synthesis of Omega-Functionalized N-Alkanethiols and Disulfides-the Building Blocks of Self-Assembled Monolayers Curr. Org. Chem. 2004, 8, 1763-1797
4. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology Chem. Rev. 2005, 105, 1103-1170
5. Huang, L.; Reekmans, G.; Saerens, D.; Friedt, J.-M.; Frederix, F.; Francis, L.; Muyldermans, S.; Campitelli, A.; Hoof, C. V. Prostate-Specific Antigen Immunosensing Based on Mixed Self-Assembled Monolayers, Camel Antibodies and Colloidal Gold Enhanced Sandwich Assays Biosens. Bioelectron. 2005, 21, 483-490
6. Frederix, F.; Bonroy, K.; Laureyn, W.; Reekmans, G.; Campitelli, A.; Dehaen, W.; Maes, G. Enhanced Performance of an Affinity Biosensor Interface Based on Mixed Self-Assembled Monolayers of Thiols on Gold Langmuir 2003, 19, 4351-4357
7. 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. 2005, 77, 1075-1080
8. 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
9. Ostuni, E.; Yan, L.; Whitesides, G. M. The Interaction of Proteins and Cells with Self-Assembled Monolayers of Alkanethiolates on Gold and Silver Colloids Surf., B 1999, 15, 3-30
10. Scholten, A.; Menges, B.; Juebner, M.; Rothschild, M. A.; Bender, K. A Mixed Alkanethiol Based Immunosensor for Surface Plasmon Field-Enhanced Fluorescence Spectroscopy in Serum Analyst 2013, 138, 1705-1712
11. Prime, K. L.; Whitesides, G. M. Self-Assembled Organic Monolayers-Model Systems for Studying Adsorption of Proteins at Surfaces Science 1991, 252, 1164-1167
12. Lahiri, J.; Isaacs, L.; Tien, J.; Whitesides, G. M. A Strategy for the Generation of Surfaces Presenting Ligands for Studies of Binding Based on an Active Ester as a Common Reactive Intermediate: A Surface Plasmon Resonance Study Anal. Chem. 1999, 71, 777-790
13. Choi, S.; Murphy, W. L. Multifunctional Mixed Sams That Promote Both Cell Adhesion and Noncovalent DNA Immobilization Langmuir 2008, 24, 6873-6880
14. Nagatomo, K.; Kawaguchi, T.; Miura, N.; Toko, K.; Matsumoto, K. Development of a Sensitive Surface Plasmon Resonance Immunosensor for Detection of 2,4-Dinitrotoluene with a Novel Oligo (Ethylene Glycol)-Based Sensor Surface Talanta 2009, 79, 1142-1148
15. Bain, C. D.; Whitesides, G. M. Modeling Organic Surfaces with Self-Assembled Monolayers Angew. Chem., Int. Ed. Engl. 1989, 28, 506-512
16. Choo, H.; Cutler, E.; Shon, Y.-S. Synthesis of Mixed Monolayer-Protected Gold Clusters from Thiol Mixtures: Variation in the Tail Group, Chain Length, and Solvent Langmuir 2003, 19, 8555-8559
17. Park, J. H.; Park, B. S.; Huh, G.; Lee, S. H.; Lee, H. S.; Cho, I. H.; Paek, S. H.; Lee, H. W. Specific Immobilization of Streptavidin on Mixed Self-Assembled Monolayers as Mixing Ratio Solid State Phenom. 2007, 121, 495-498
18. Polster, D.; Graaf, H. Advancing and Receding Angles: Dynamic Contact Angle Measurements on Mixed Alkyl Monolayers Appl. Surf. Sci. 2012, 265, 88-93
19. Nelson, K. E.; Gamble, L.; Jung, L. S.; Boeckl, M. S.; Naeemi, E.; Golledge, S. L.; Sasaki, T.; Castner, D. G.; Campbell, C. T.; Stayton, P. S. Surface Characterization of Mixed Self-Assembled Monolayers Designed for Streptavidin Immobilization Langmuir 2001, 17, 2807-2816
20. Chapman, R. G.; Ostuni, E.; Yan, L.; Whitesides, G. M. Preparation of Mixed Self-Assembled Monolayers (Sams) That Resist Adsorption of Proteins Using the Reaction of Amines with a Sam That Presents Interchain Carboxylic Anhydride Groups Langmuir 2000, 16, 6927-6936
21. Zorn, S.; Dettinger, U.; Skoda, M. W. A.; Jacobs, R. M. J.; Peisert, H.; Gerlach, A.; Chassé, T.; Schreiber, F. Stability of Hexa(Ethylene Glycol) Sams Towards the Exposure to Natural Light and Repeated Reimmersion Appl. Surf. Sci. 2010, 258, 7882-7888
22. Shuster, M. J.; Vaish, A.; Gilbert, M. L.; Martinez-Rivera, M.; Nezarati, R. M.; Weiss, P. S.; Andrews, A. M. Comparison of Oligo(Ethylene Glycol)Alkanethiols Versus N-Alkanethiols: Self-Assembly, Insertion, and Functionalization J. Phys. Chem. C 2011, 115, 24778-24787
23. Lin, Y.-C.; Yu, B.-Y.; Lin, W.-C.; Lee, S.-H.; Kuo, C.-H.; Shyue, J.-J. Tailoring the Surface Potential of Gold Nanoparticles with Self-Assembled Monolayers with Mixed Functional Groups J. Colloid Interface Sci. 2009, 340, 126-130
24. Chirakul, P.; Pérez-Luna, V. H.; Owen, H.; López, G. P.; Hampton, P. D. Synthesis and Characterization of Amine-Terminated Self-Assembled Monolayers Containing Diethylene Glycol Linkages Langmuir 2002, 18, 4324-4330
25. Jung, L. S.; Campbell, C. T.; Chinowsky, T. M.; Mar, M. N.; Yee, S. S. Quantitative Interpretation of the Response of Surface Plasmon Resonance Sensors to Adsorbed Films Langmuir 1998, 14, 5636-5648
26. Cheng, F.; Gamble, L. J.; Castner, D. G. XPS, Tof-Sims, NEXAFS, and SPR Characterization of Nitrilotriacetic Acid-Terminated Self-Assembled Monolayers for Controllable Immobilization of Proteins Anal. Chem. 2008, 80, 2564-2573
27. Bae, Y. M.; Oh, B.-K.; Lee, W.; Lee, W. H.; Choi, J.-W. Study on Orientation of Immunoglobulin G on Protein G Layer Biosens. Bioelectron. 2005, 21, 103-110
28. Pavan, S.; Berti, F. Short Peptides as Biosensor Transducers Anal. Bioanal. Chem. 2010, 402, 3055-3070
29. Yang, H.; Gurgel, P. V.; Carbonell, R. G. Hexamer Peptide Affinity Resins That Bind the Fc Region of Human Immunoglobulin G J. Pept. Res. 2005, 66, 120-137
30. Menegatti, S.; Naik, A. D.; Gurgel, P. V.; Carbonell, R. G. Alkaline-Stable Peptide Ligand Affinity Adsorbents for the Purification of Biomolecules J. Chromatogr. A 2010, 1245, 55-64
31. Naik, A. D.; Menegatti, S.; Gurgel, P. V.; Carbonell, R. G. Performance of Hexamer Peptide Ligands for Affinity Purification of Immunoglobulin G from Commercial Cell Culture Media J. Chromatogr. A 2011, 1218, 1691-1700
32. Zhang, Y.; Islam, N.; Carbonell, R. G.; Rojas, O. J. Specific Binding of IgG with Bioactive Short Peptides Supported on Antifouling Copolymer Layers for Detection in QCM and SPR Anal. Chem. 2012, 85, 1106-1113
33. Yu, Q.; Chen, S.; Taylor, A. D.; Homola, J.; Hock, B.; Jiang, S. Detection of Low-Molecular-Weight Domoic Acid Using Surface Plasmon Resonance Sensor Sens. Actuators, B 2005, 107, 193-201
34. Wang, H.; Chen, S.; Li, L.; Jiang, S. Improved Method for the Preparation of Carboxylic Acid and Amine Terminated Self-Assembled Monolayers of Alkanethiolates Langmuir 2005, 21, 2633-2636
35. Johansson, L.-S.; Campbell, J. M. Reproducible XPS on Biopolymers: Cellulose Studies Surf. Interface Anal. 2004, 36, 1018-1022
36. Cooper, E.; Leggett, G. J. Static Secondary Ion Mass Spectrometry Studies of Self-Assembled Monolayers: Influence of Adsorbate Chain Length and Terminal Functional Group on Rates of Photooxidation of Alkanethiols on Gold Langmuir 1998, 14, 4795-4801
37. Pan, S.; Castner, D. G.; Ratner, B. D. Multitechnique Surface Characterization of Derivatization Efficiencies for Hydroxyl-Terminated Self-Assembled Monolayers Langmuir 1998, 14, 3545-3550
38. Offord, D. A.; John, C. M.; Griffin, J. H. Contact Angle Goniometry, Ellipsometry, XPS, and Tof-Sims Analysis of Gold-Supported, Mixed Self-Assembled Monolayers Formed from Mixed Dialkyl Disulfides Langmuir 1994, 10, 761-766
39. Wolf, K. V.; Cole, D. A.; Bernasek, S. L. Chain Length Effects for Cluster Ion Formation During High Energy Ion/Surface Collisions with Self-Assembled Monolayer Surfaces J. Phys. Chem. B 2002, 106, 10382-10387
40. Baugh, L.; Weidner, T.; Baio, J. E.; Nguyen, P.-C. T.; Gamble, L. J.; Stayton, P. S.; Castner, D. G. Probing the Orientation of Surface-Immobilized Protein G B1 Using ToF-SIMS, Sum Frequency Generation, and NEXAFS Spectroscopy Langmuir 2010, 26, 16434-16441
41. Cheng, F.; Gamble, L. J.; Grainger, D. W.; Castner, D. G. X-Ray Photoelectron Spectroscopy, Time-of-Flight Secondary Ion Mass Spectrometry, and Principal Component Analysis of the Hydrolysis, Regeneration, and Reactivity of N-Hydroxysuccinimide-Containing Organic Thin Films Anal. Chem. 2007, 79, 8781-8788
42. Arwin, H. Is Ellipsometry Suitable for Sensor Applications? Sens. Actuators A: Phys. 2001, 92, 43-51
43. Karlsson, R.; Michaelsson, A.; Mattsson, L. Kinetic Analysis of Monoclonal Antibody-Antigen Interactions with a New Biosensor Based Analytical System J. Immunol. Methods 1991, 145, 229-240
44. Wirde, M.; Gelius, U.; Nyholm, L. Self-Assembled Monolayers of Cystamine and Cysteamine on Gold Studied by XPS and Voltammetry Langmuir 1999, 15, 6370-6378
45. Mrksich, M. Mass Spectrometry of Self-Assembled Monolayers: A New Tool for Molecular Surface Science ACS Nano 2008, 2, 7-18
46. Tosatti, S.; Michel, R.; Textor, M.; Spencer, N. D. Self-Assembled Monolayers of Dodecyl and Hydroxy-Dodecyl Phosphates on Both Smooth and Rough Titanium and Titanium Oxide Surfaces Langmuir 2002, 18, 3537-3548
47. Folkers, J. P.; Laibinis, P. E.; Whitesides, G. M. Self-Assembled Monolayers of Alkanethiols on Gold: Comparisons of Monolayers Containing Mixtures of Short- and Long-Chain Constituents with Methyl and Hydroxymethyl Terminal Groups Langmuir 1992, 8, 1330-1341
48. Park, H. H.; Ivanisevic, A. Formation and Characterization of Homogeneous and Mixed Self-Assembled Monolayers of Peptides and Alkanethiols on Indium Phosphide Surfaces J. Phys. Chem. C 2007, 111, 3710-3718
49. Riepl, M.; Enander, K.; Liedberg, B.; Schäferling, M.; Kruschina, M.; Ortigao, F. Functionalized Surfaces of Mixed Alkanethiols on Gold as a Platform for Oligonucleotide Microarrays Langmuir 2002, 18, 7016-7023
50. Mehne, J.; Markovic, G.; Pröll, F.; Schweizer, N.; Zorn, S.; Schreiber, F.; Gauglitz, G. n. Characterisation of Morphology of Self-Assembled PEG Monolayers: A Comparison of Mixed and Pure Coatings Optimised for Biosensor Applications Anal. Bioanal. Chem. 2008, 391, 1783-1791
51. Bain, C. D.; Evall, J.; Whitesides, G. M. Formation of Monolayers by the Coadsorption of Thiols on Gold: Variation in the Head Group, Tail Group, and Solvent J. Am. Chem. Soc. 1989, 111, 7155-7164
52. Kang, J. F.; Liao, S.; Jordan, R.; Ulman, A. Mixed Self-Assembled Monolayers of Rigid Biphenyl Thiols: Impact of Solvent and Dipole Moment J. Am. Chem. Soc. 1998, 120, 9662-9667
53. Arima, Y.; Iwata, H. Effect of Wettability and Surface Functional Groups on Protein Adsorption and Cell Adhesion Using Well-Defined Mixed Self-Assembled Monolayers Biomaterials 2007, 28, 3074-3082
54. Faucheux, N.; Schweiss, R.; Lützow, K.; Werner, C.; Groth, T. Self-Assembled Monolayers with Different Terminating Groups as Model Substrates for Cell Adhesion Studies Biomaterials 2004, 25, 2721-2730
55. Extrand, C. W. Contact Angles and Hysteresis on Surfaces with Chemically Heterogeneous Islands Langmuir 2003, 19, 3793-3796
56. mOH on Gold J. Am. Chem. Soc. 1991, 113, 12-20
57. Wink, T.; vanZuilen, S. J.; Bult, A.; vanBennekom, W. P. Self-Assembled Monolayers for Biosensors Analyst 1997, 122, R43-R50
58. Briand, E.; Salmain, M.; Compère, C.; Pradier, C.-M. Immobilization of Protein A on Sams for the Elaboration of Immunosensors Colloids Surf., B 2006, 53, 215-224
59. Wang, D. S.; Chang, C. C.; Shih, S. C.; Lin, C. W. An Ellipsometric Study on the Density and Functionality of Antibody Layers Immobilized by a Randomly Covalent Method and a Protein A-Oriented Method Biomed. Eng.-Appl. Basis Commun. 2009, 21, 303-310
60. Unsworth, L. D.; Sheardown, H.; Brash, J. L. Protein Resistance of Surfaces Prepared by Sorption of End-Thiolated Poly(Ethylene Glycol) to Gold: Effect of Surface Chain Density Langmuir 2005, 21, 1036-1041
61. 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, 406-416
62. Berry, J. D. Rational Monoclonal Antibody Development to Emerging Pathogens, Biothreat Agents and Agents of Foreign Animal Disease: The Antigen Scale Vet. J. 2005, 170, 193-211
63. Spinke, J.; Liley, M.; Schmitt, F. J.; Guder, H. J.; Angermaier, L.; Knoll, W. Molecular Recognition at Self-Assembled Monolayers: Optimization of Surface Functionalization J. Chem. Phys. 1993, 99, 7012-7019
64. Islam, N. Surface Plasmon Resonance Studies of the Specific Interactions of Hexamer Peptide Ligands with Human Immunoglobulin G, Phd Thesis, North Carolina State University, Raleigh, NC, 2013.
65. Kim, J. Y.; Kim, Y.-G.; Lee, G. M. Cho Cells in Biotechnology for Production of Recombinant Proteins: Current State and Further Potential Appl. Microbiol. Biotechnol. 2012, 93, 917-930
66. Yang, H. O.; Gurgel, P. V.; Williams, D. K.; Bobay, B. G.; Cavanagh, J.; Muddiman, D. C.; Carbonell, R. G. Binding Site on Human Immunoglobulin G for the Affinity Ligand HWRGWV J. Mol. Recognit. 2010, 23, 271-282
67. Yang, H.; Gurgel, P. V.; Carbonell, R. G. Purification of Human Immunoglobulin G Via Fc-Specific Small Peptide Ligand Affinity Chromatography J. Chromatogr. A 2009, 1216, 910-918