An intramolecular O-N migration reaction on gold surfaces: Toward the preparation of well-defined amyloid surfaces

ACS Nano

Volumn 3, Issue 10, 2009, Pages 3091-3097

  Boussert, Stephanie ^a,b   Diez Perez, Ismael ^c   Kogan, Marcelo J ^d   De Oliveira, Eliandre ^a   Giralt, Ernest ^b,c  

^a Proteomics Platform   (Spain)

^b INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d CIMAT   (Chile)

Author keywords

Atomic force microscopy (AFM); Gold surface; Protein protein interaction; Proteomics; Selfassembled monolayers for matrix assisted laser desorption ionization time of flight mass spectrometry (SAMDI TOF MS); Amyloid

Indexed keywords

ATOMIC FORCE MICROSCOPY; BODY FLUIDS; DESORPTION; GLYCOPROTEINS; GOLD; GOLD METALLURGY; INDUCTIVELY COUPLED PLASMA; MASS SPECTROMETRY; NEURODEGENERATIVE DISEASES; PEPTIDES; SELF ASSEMBLED MONOLAYERS;

CENTRAL NERVOUS SYSTEMS; FUNCTIONALIZED SURFACES; GOLD SURFACES; MATRIX ASSISTED LASER DESORPTION/IONIZATION; MATRIX-ASSISTED LASER DESORPTION/IONIZATION-TIME-OF-FLIGHT MASS SPECTROMETRY; PROTEIN-PROTEIN COMPLEXES; PROTEIN-PROTEIN INTERACTIONS; PROTEOMICS;

SURFACE REACTIONS;

AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; BOVINE SERUM ALBUMIN; GOLD; NITROGEN; OXYGEN; PEPTIDE FRAGMENT; SERUM AMYLOID P;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; CATTLE; CHEMISTRY; HUMAN; METABOLISM; MOLECULAR GENETICS; SURFACE PROPERTY; SYNTHESIS;

AMINO ACID SEQUENCE; AMYLOID BETA-PROTEIN; ANIMALS; CATTLE; GOLD; HUMANS; MOLECULAR SEQUENCE DATA; NITROGEN; OXYGEN; PEPTIDE FRAGMENTS; SERUM ALBUMIN, BOVINE; SERUM AMYLOID P-COMPONENT; SURFACE PROPERTIES;

EID: 70350647623     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn900935p     Document Type: Article

References (42)

1. Selkoe, D. J. Alzheimer's Disease: Genes, Proteins, and Therapy. Physiol. Rev. 2001, 81, 741-766.
2. Wolfe, M. S. Therapeutic Strategies for Alzheimer's Disease. Nat. Rev. Drug Discovery 2002, 1, 859-866.
3. Rottkamp, C. A.; Atwood, C. S.; Joseph, J. A.; Nunomura, A.; Perry, G.; Smith, M. A. The State versus Amyloid-Beta: The Trial of the Most Wanted Criminal in Alzheimer's Disease. Peptides 2002, 23, 1333-1341.
4. Ferreira, S. T.; Vieira, M. N.; De Felice, F. G. Soluble Protein Oligomers as Emerging Toxins in Alzheimer's and Other Amyloid Diseases. IUBMB Life 2007, 59, 332-345.
5. Glabe, C. C. Amyloid Accumulation and Pathogenesis of Alzheimer's Disease: Significance of Monomeric, Oligomeric and Fibrillar A-Beta. Subcell. Biochem. 2005, 38, 167-177.
6. Haass, C.; Selkoe, D. J. Soluble Protein Oligomers in Neurodegeneration: Lessons from the Alzheimer's Amyloid Beta-Peptide. Nat. Rev. Mol. Cell. Biol. 2007, 8, 101-112.
7. Walsh, D. M.; Selkoe, D. J. A-Beta OligomersOA Decade of Discovery. J. Neurochem. 2007, 101, 1172-1184.
8. Merrifield, R. B. J. Solid Phase Peptide Synthesis. The Synthesis of a Tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
9. Mutter, M.; Nefzi, A.; Sato, T.; Sun, X.; Wahl, F.; Wohr, T. Pseudo-Prolines (psi pro) for Accessing «Inaccessible» Peptides. Pept. Res. 1995, 8, 145-153.
10. Sohma, Y.; Hayashi, Y.; Skwarczynski, M.; Hamada, Y.; Sasaki, M.; Kimura, T.; Kiso, Y. O-N Intramolecular Acyl Migration Reaction in the Development of Prodrugs and the Synthesis of Difficult Sequence-Containing Bioactive Peptides. Biopolymers 2004, 76, 344-356. (Pubitemid 39468257)
11. Kodadek, T. Protein Microarrays: Prospects and Problems. Chem. Biol. 2001, 8, 105-115.
12. Cahill, D. J. Protein and Antibody Arrays and their Medical Applications. J. Immunol. Methods 2001, 250, 81-91.
13. Wilson, D. S.; Nock, S. Functional Protein Microarray. Curr. Opin. Chem. Biol. 2002, 6, 81-85.
14. Zhu, H.; Snyder, M. Protein Chip Technology. Curr. Opin. Chem. Biol. 2003, 7, 55-63.
15. Mrksich, M.; Whitesides, G. M. Using Self-Assembled Monolayers to Understand the Interactions of Man-Made Surfaces with Proteins and Cells. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 55-78.
16. 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, 1103-1169.
17. Frutos, A. G.; Liu, Q.; Thiel, A. J.; Sanner, A. M.; Condon, A. E.; Smith, L. M.; Corn, R. M. Demonstration of a Word Design Strategy for DNA Computing on Surfaces. Nucleic Acids Res. 1997, 25, 4748-4757.
18. Sigal, G. B.; Bamdad, C.; Barberis, A.; Strominger, J.; Whitesides, G. M. A Self-Assembled Monolayer for the Binding and Study of Histidine-Tagged Proteins by Surface Plasmon Resonance. Anal. Chem. 1996, 68, 490-497.
19. Muller, W.; Ringsdorf, H.; Rump, E.; Wildburg, G.; Zhang, X.; Angermaier, L.; Knoll, W.; Liley, M.; Spinke, J. Attempts to Mimic Docking Processes of the Immune System: Recognition Induced Formation of Protein Multilayers. Science 1993, 262, 1706-1708.
20. Mrksich, M.; Chen, C. S.; Xia, Y.; Dike, L. E.; Ingber, D. E.; Whitesides, G. M. Controlling Cell Attachment on Contoured Surfaces with Self-Assembled Monolayers of Alkanethiolates on Gold. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 10775-10778.
21. Houseman, B. T.; Mrksich, M. The Microenvironment of Immobilized Arg-Gly-Asp Peptides is an Important Determinant of Cell Adhesion. Biomaterials 2001, 22, 943-955.
22. Vericat, C.; Vela, M. E.; Salvarezza, R. C. Self-Assembled Monolayers of Alkanethiols on Au (111) : Surface Structures, Defects and Dynamics. Phys. Chem. Chem. Phys. 2005, 7, 3258-3268.
23. Prime, K. L.; Whitesides, G. M. Self-Assembled Organic Monolayers: Model Systems for Studying Adsorption of Proteins at Surfaces. Science 1991, 252, 1164-1167.
24. Siegel, R. R.; Harder, P.; Dahint, R.; Grunze, M.; Josse, F.; Mrksich, M.; Whitesides, G. M. On-Line Detection of Nonspecific Protein Adsorption at Artificial Surfaces. Anal. Chem. 1997, 69, 3321-3328.
25. Min, D. H.; Su, J.; Mrksich, M. Profiling Kinase Activities by Using a Peptide Chip and Mass Spectrometry. Angew. Chem., Int. Ed. 2004, 43, 5973-5977.
26. Min, D. H.; Tang, W. J.; Mrksich, M. Chemical Screening by Mass Spectrometry to Identify Inhibitors of Anthrax Lethal Factor. Nat. Biotechnol. 2004, 22, 717-723.
27. Yeo, W. S.; Mrksich, M. Electroactive Substrates that Reveal Aldehyde Groups for Bio-Immobilization. Adv. Mater. 2004, 16, 1352-1356.
28. Houseman, B. T.; Gawalt, E. S.; Mrksich, M. Maleimide-Functionalized Self-Assembled Monolayers for the Preparation of Peptide and Carbohydrate Biochips. Langmuir 2003, 19, 1522-1531.
29. Yang, J.; Mou, J.; Shao, Z. Molecular Resolution Atomic Force Microscopy of Soluble Proteins in Solution. Biochim. Biophys. Acta 1994, 1199, 105-114.
30. Scheuring, S. AFM Studies of the Supramolecular Assembly of Bacterial Photosynthetic Core-Complexes. Curr. Opin. Chem. Biol. 2006, 10, 387-393.
31. Scheuring, S.; Boudier, T.; Sturgis, J. N. From High-Resolution AFM Topographs to Atomic Models of Supramolecular Assemblies. J. Struct. Biol. 2007, 159, 268-276.
32. Sohma, Y.; Hayashi, Y.; Kimura, M.; Chiyomori, Y.; Taniguchi, A.; Sasaki, M.; Kimura, T.; Kiso, Y. The 'O-Acyl Click-Peptide Method' for the Synthesis of Difficult Sequence-Containing Peptides: Application to the Synthesis of Alzheimer's Disease-Related Amyloid Beta Peptide (Abeta) 1=42. J. Pept. Sci. 2005, 11, 441-451.
33. Petkova, A. T.; Ishii, Y.; Balbach, J. J.; Antzutkin, O. N.; Leapman, R. D.; Delaglio, F.; Tycko, R. A. Structural Model for Alzheimer's Beta-Amyloid Fibrils Based on Experimental Constraints from Solid State NMR. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 16742-16747.
34. Yang, J.; Mayer, M.; Kriebel, J. K.; Garstecki, P.; Whitesides, G. M. Self-Assembled Aggregates of IgGs as Templates for the Growth of Clusters of Gold Nanoparticles. Angew. Chem., Int. Ed. 2004, 43, 1555-1558.
35. Thomson, N. H. The Substructure of Immunoglobulin G Resolved to 25 kDa Using Amplitude Modulation AFM in Air. Ultramicroscopy 2005, 105, 103-110.
36. Liko, I.; Mak, M.; Klement, E.; Hunyadi-Gulyas, E.; Pazmany, T.; Medzihradszky, K. F.; Urbanyi, Z. Evidence for an Extended Interacting Surface Between Beta-Amyloid and Serum Amyloid P Component. Neurosci. Lett. 2007, 412, 51-55.
37. Urbanyi, Z.; Laszlo, L.; Tomasi, T. B.; Toth, E.; Mekes, E.; Sass, M.; Pazmany, T. Serum Amyloid P Component Induces Neuronal Apoptosis and Beta-Amyloid Immunoreactivity. Brain Res. 2003, 988, 69-77.
38. Kalaria, R. N.; Grahovac, I. Serum Amyloid P Immunoreactivity in Hippocampal Tangles, Plaques and Vessels: Implications for Leakage Across the Blood=Brain Barrier in Alzheimer's Disease. Brain Res. 1990, 516, 349-353.
39. Kalaria, R.; Galloway, P. G. Widespread Serum Amyloid P Immunoreactivity in Cortical Amyloid Deposits and the Neurofibrillary Pathology of Alzheimer's Disease and Other Degenerative Disorders. Neuropathol. Appl. Neurobiol. 1991, 17, 189-201.
40. Perlmutter, L. S.; Barrón, E.; Myers, M.; Saperia, D.; Chui, H. C. Localization of Amyloid P Component in Human Brain: Vascular Staining Patterns and Association with Alzheimer's Disease Lesions. J. Comp. Neurol. 1995, 352, 92-105.
41. Hamazaki, H. Ca (2=) -Dependent Binding of Human Serum Amyloid P Component to Alzheimer's Beta-Amyloid Peptide. J. Biol. Chem. 1995, 270, 10392-10394.
42. Oncins, G.; Vericat, C.; Sanz, F. Mechanical Properties of Alkanethiol Monolayers Studied by Force Spectroscopy. J. Chem. Phys. 2008, 128, 044701-044709.