Colloidal stability of gold nanoparticles coated with multithiol- poly(ethylene glycol) ligands: Importance of structural constraints of the sulfur anchoring groups

Journal of Physical Chemistry C

Volumn 117, Issue 37, 2013, Pages 18947-18956

  Oh, Eunkeu ^a,b   Susumu, Kimihiro ^a,b   Mäkinen, Antti J ^b   Deschamps, Jeffrey R ^b   Huston, Alan L ^b   Medintz, Igor L ^b  

^a SOTERA DEFENSE SOLUTIONS   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLLOIDAL STABILITY; COMPACT STRUCTURES; ENERGY MINIMIZATION; ENVIRONMENTAL CONDITIONS; GOLD NANOPARTICLE; GOLD NANOPARTICLES; HIGH SALT CONCENTRATION; STRUCTURAL CONSTRAINTS;

CHELATION; GOLD; METAL NANOPARTICLES; PHOTOELECTRONS; POLYETHYLENE GLYCOLS; STABILITY; SULFUR; SULFUR COMPOUNDS; X RAY PHOTOELECTRON SPECTROSCOPY;

LIGANDS;

EID: 84884575416     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp405265u     Document Type: Article

References (63)

1. Kim, S. T.; Saha, K.; Kim, C.; Rotello, V. M. The Role of Surface Functionality in Determining Nanoparticle Cytotoxicity Acc. Chem. Res. 2013, 46 (3) 681-691
2. Su, S.; Zuo, X. L.; Pan, D.; Pei, H.; Wang, L. H.; Fan, C. H.; Huang, W. Design and Applications of Gold Nanoparticle Conjugates by Exploiting Biomolecule-Gold Nanoparticle Interactions Nanoscale 2013, 5 (7) 2589-2599
3. Sapsford, K. E.; Algar, W. R.; Berti, L.; Gemmill, K. B.; Casey, B. J.; Oh, E.; Stewart, M. H.; Medintz, I. L. Functionalizing Nanoparticles with Biological Molecules: Developing Chemistries that Facilitate Nanotechnology Chem. Rev. 2013, 113 (3) 1904-2074
4. Saha, K.; Agasti, S. S.; Kim, C.; Li, X. N.; Rotello, V. M. Gold Nanoparticles in Chemical and Biological Sensing Chem. Rev. 2012, 112 (5) 2739-2779
5. Alivisatos, P. The Use of Nanocrystals in Biological Detection Nat. Biotechnol. 2004, 22 (1) 47-52
6. Daniel, M. C.; Astruc, D. Gold Nanoparticles: Assembly, Supramolecular Chemistry, Quantum-Size-Related Properties, and Applications Toward Biology, Catalysis, and Nanotechnology Chem. Rev. 2004, 104 (1) 293-346
7. Katz, E.; Willner, I. Integrated Nanoparticle-Biomolecule Hybrid Systems: Synthesis, Properties, and Applications Angew. Chem., Int. Ed. Engl. 2004, 43 (45) 6042-6108
8. Rosi, N. L.; Mirkin, C. A. Nanostructures in Biodiagnostics Chem. Rev. 2005, 105 (4) 1547-1562
9. Medintz, I. L.; Uyeda, H. T.; Goldman, E. R.; Mattoussi, H. Quantum Dot Bioconjugates for Imaging, Labelling and Sensing Nat. Mater. 2005, 4 (6) 435-446
10. Jennings, T.; Strouse, G. Past, Present, and Future of Gold Nanoparticles Adv. Exp. Med. Biol. 2007, 620, 34-47
11. Sardar, R.; Funston, A. M.; Mulvaney, P.; Murray, R. W. Gold Nanoparticles: Past, Present, and Future Langmuir 2009, 25 (24) 13840-13851
12. Nel, A. E.; Madler, L.; Velegol, D.; Xia, T.; Hoek, E. M. V.; Somasundaran, P.; Klaessig, F.; Castranova, V.; Thompson, M. Understanding Biophysicochemical Interactions at the Nano-Bio Interface Nat. Mater. 2009, 8 (7) 543-557
13. Otsuka, H.; Nagasaki, Y.; Kataoka, K. PEGylated Nanoparticles for Biological and Pharmaceutical Applications Adv. Drug Delivery Rev. 2012, 64, 246-255
14. Oh, E.; Fatemi, F. K.; Currie, M.; Delehanty, J. B.; Pons, T.; Fragola, A.; Leveque-Fort, S.; Goswami, R.; Susumu, K.; Huston, A. L.; Medintz, I. L. PEGylated Luminescent Gold Nanoclusters: Synthesis, Characterization, Bioconjugation, and Application to One- and Two-Photon Cellular Imaging Part. Part. Syst. Charact. 2013, 30 (5) 453-466
15. Leduc, C.; Si, S.; Gautier, J.; Soto-Ribeiro, M.; Wehrle-Haller, B.; Gautreau, A.; Giannone, G.; Cognet, L.; Lounis, B. A Highly Specific Gold Nanoprobe for Live-Cell Single-Molecule Imaging Nano Lett. 2013, 13 (4) 1489-1494
16. Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, 2008.
17. 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 (4) 1103-1169
18. Pons, T.; Medintz, I. L.; Sapsford, K. E.; Higashiya, S.; Grimes, A. F.; English, D. S.; Mattoussi, H. On the Quenching of Semiconductor Quantum Dot Photoluminescence by Proximal Gold Nanoparticles Nano Lett. 2007, 7 (10) 3157-3164
19. Schulz, F.; Vossmeyer, T.; Bastús, N. G.; Weller, H. Effect of the Spacer Structure on the Stability of Gold Nanoparticles Functionalized with Monodentate Thiolated Poly(ethylene glycol) Ligands Langmuir 2013, 29 (31) 9897-9908
20. Algar, W. R.; Prasuhn, D. E.; Stewart, M. H.; Jennings, T. L.; Blanco-Canosa, J. B.; Dawson, P. E.; Medintz, I. L. The Controlled Display of Biomolecules on Nanoparticles: A Challenge Suited to Bioorthogonal Chemistry Bioconjugate Chem. 2011, 22 (5) 825-858
21. Kimling, J.; Maier, M.; Okenve, B.; Kotaidis, V.; Ballot, H.; Plech, A. Turkevich Method for Gold Nanoparticle Synthesis Revisited J. Phys. Chem. B 2006, 110 (32) 15700-15707
22. CORE ∼1.5 nm) Phosphine-Stabilized Gold Nanoparticles J. Am. Chem. Soc. 2000, 122 (51) 12890-12891
23. Jana, N. R.; Gearheart, L.; Murphy, C. J. Seeding Growth for Size Control of 5-40 nm Diameter Gold Nanoparticles Langmuir 2001, 17 (22) 6782-6786
24. Green, M.; O'Brien, P. A Simple One Phase Preparation of Organically Capped Gold Nanocrystals Chem. Commun. 2000, 183-184
25. Aslam, M.; Fu, L.; Su, M.; Vijayamohanan, K.; Dravid, V. P. Novel One-Step Synthesis of Amine-Stabilized Aqueous Colloidal Gold Nanoparticles J. Mater. Chem. 2004, 14 (12) 1795-1797
26. Selvakannan, P. R.; Mandal, S.; Phadtare, S.; Pasricha, R.; Sastry, M. Capping of Gold Nanoparticles by the Amino Acid Lysine Renders Them Water-Dispersible Langmuir 2003, 19 (8) 3545-3549
27. Gandubert, V. J.; Lennox, R. B. Assessment of 4-(Dimethylamino)pyridine as a Capping Agent for Gold Nanoparticles Langmuir 2005, 21 (14) 6532-6539
28. Sharma, J.; Chhabra, R.; Yan, H.; Liu, Y. A Facile in situ Generation of Dithiocarbamate Ligands for Stable Gold Nanoparticle-Oligonucleotide Conjugates Chem. Commun. 2008, 2140-2142
29. Kim, F.; Connor, S.; Song, H.; Kuykendall, T.; Yang, P. D. Platonic Gold Nanocrystals Angew. Chem., Int. Ed. 2004, 43 (28) 3673-3677
30. Lee, Y.; Lee, S. H.; Kim, J. S.; Maruyama, A.; Chen, X. S.; Park, T. G. Controlled Synthesis of PEI-coated Gold Nanoparticles using Reductive Catechol Chemistry for siRNA Delivery J. Controlled Release 2011, 155 (1) 3-10
31. Hussain, I.; Graham, S.; Wang, Z. X.; Tan, B.; Sherrington, D. C.; Rannard, S. P.; Cooper, A. I.; Brust, M. Size-Controlled Synthesis of Near-Monodisperse Gold Nanoparticles in the 1-4 nm Range Using Polymeric Stabilizers J. Am. Chem. Soc. 2005, 127 (47) 16398-16399
32. You, C. C.; Miranda, O. R.; Gider, B.; Ghosh, P. S.; Kim, I. B.; Erdogan, B.; Krovi, S. A.; Bunz, U. H. F.; Rotello, V. M. Detection and Identification of Proteins Using Nanoparticle-Fluorescent Polymer "Chemical Nose" Sensors Nat. Nanotechnol. 2007, 2 (5) 318-323
33. Liz-Marzan, L. M.; Giersig, M.; Mulvaney, P. Synthesis of Nanosized Gold-Silica Core-Shell Particles Langmuir 1996, 12 (18) 4329-4335
34. Kairdolf, B. A.; Nie, S. M. Multidentate-Protected Colloidal Gold Nanocrystals: pH Control of Cooperative Precipitation and Surface Layer Shedding J. Am. Chem. Soc. 2011, 133 (19) 7268-7271
35. Brust, M.; Walker, M.; Bethell, D.; Schiffrin, D. J.; Whyman, R. Synthesis of Thiol-Derivatized Gold Nanoparticles in a Two-Phase Liquid-Liquid System J. Chem. Soc., Chem. Commun. 1994, 7) 801-802
36. Yonezawa, T.; Kunitake, T. Practical Preparation of Anionic Mercapto Ligand-Stabilized Gold Nanoparticles and Their Immobilization Colloids Surf. A Physicochemical. Eng. Aspects 1999, 149 (1-3) 193-199
37. Brinas, R. P.; Hu, M. H.; Qian, L. P.; Lymar, E. S.; Hainfeld, J. F. Gold Nanoparticle Size Controlled by Polymeric Au(I) Thiolate Precursor Size J. Am. Chem. Soc. 2008, 130 (3) 975-982
38. Kanaras, A. G.; Kamounah, F. S.; Schaumburg, K.; Kiely, C. J.; Brust, M. Thioalkylated Tetraethylene Glycol: A New Ligand for Water Soluble Monolayer Protected Gold Clusters Chem. Commun. 2002, 2294-2295
39. 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. 1998, 120 (48) 12696-12697
40. Oh, E.; Susumu, K.; Blanco-Canosa, J. B.; Medintz, I. L.; Dawson, P. E.; Mattoussi, H. Preparation of Stable Maleimide-Functionalized Au Nanoparticles and Their Use in Counting Surface Ligands Small 2010, 6 (12) 1273-1278
41. Oh, E.; Susumu, K.; Goswami, R.; Mattoussi, H. One-Phase Synthesis of Water-Soluble Gold Nanoparticles with Control over Size and Surface Functionalities Langmuir 2010, 26 (10) 7604-7613
42. Susumu, K.; Uyeda, H. T.; Medintz, I. L.; Pons, T.; Delehanty, J. B.; Mattoussi, H. Enhancing the Stability and Biological Functionalities of Quantum Dots via Compact Multifunctional Ligands J. Am. Chem. Soc. 2007, 129 (45) 13987-13996
43. Li, Z.; Jin, R. C.; Mirkin, C. A.; Letsinger, R. L. Multiple Thiol-Anchor Capped DNA-Gold Nanoparticle Conjugates Nucleic Acids Res. 2002, 30 (7) 1558-1562
44. Levy, R.; Thanh, N. T. K.; Doty, R. C.; Hussain, I.; Nichols, R. J.; Schiffrin, D. J.; Brust, M.; Fernig, D. G. Rational and Combinatorial Design of Peptide Capping Ligands for Gold Nanoparticles J. Am. Chem. Soc. 2004, 126 (32) 10076-10084
45. Tkachenko, A. G.; Xie, H.; Liu, Y. L.; Coleman, D.; Ryan, J.; Glomm, W. R.; Shipton, M. K.; Franzen, S.; Feldheim, D. L. Cellular Trajectories of Peptide-Modified Gold Particle Complexes: Comparison of Nuclear Localization Signals and Peptide Transduction Domains Bioconjugate Chem. 2004, 15 (3) 482-490
46. Oh, E.; Susumu, K.; Jain, V.; Kim, M.; Huston, A. One-Pot Aqueous Phase Growth of Biocompatible 15-130 nm Gold Nanoparticles Stabilized with Bidentate PEG J. Colloid Interface Sci. 2012, 376, 107-111
47. Susumu, K.; Oh, E.; Delehanty, J. B.; Blanco-Canosa, J. B.; Johnson, B. J.; Jain, V.; Hervey, W. J.; Algar, W. R.; Boeneman, K.; Dawson, P. E.; Medintz, I. L. Multifunctional Compact Zwitterionic Ligands for Preparing Robust Biocompatible Semiconductor Quantum Dots and Gold Nanoparticles J. Am. Chem. Soc. 2011, 133 (24) 9480-9496
48. Hou, W. B.; Dasog, M.; Scott, R. W. J. Probing the Relative Stability of Thiolate- and Dithiolate-Protected Au Monolayer-Protected Clusters Langmuir 2009, 25 (22) 12954-12961
49. Mei, B. C.; Oh, E.; Susumu, K.; Farrell, D.; Mountziaris, T. J.; Mattoussi, H. Effects of Ligand Coordination Number and Surface Curvature on the Stability of Gold Nanoparticles in Aqueous Solutions Langmuir 2009, 25 (18) 10604-10611
50. Mei, B. C.; Susumu, K.; Medintz, I. L.; Delehanty, J. B.; Mountziaris, T. J.; Mattoussi, H. Modular Poly(ethylene glycol) Ligands for Biocompatible Semiconductor and Gold Nanocrystals with Extended pH and Ionic Stability J. Mater. Chem. 2008, 18 (41) 4949-4958
51. Wan, A. S.; Long, J. P.; Kushto, G.; Makinen, A. J. The Interfacial Chemistry and Energy Level Structure of a Liquid Crystalline Perylene Derivative on Au(111) and Graphite Surfaces Chem. Phys. Lett. 2008, 463 (1-3) 72-77
52. Silien, C.; Buck, M.; Goretzki, G.; Lahaye, D.; Champness, N. R.; Weidner, T.; Zharnikov, M. Self-Assembly of a Pyridine-Terminated Thiol Monolayer on Au(111) Langmuir 2009, 25 (2) 959-967
53. Wang, J. M.; Wang, W.; Kollman, P. A.; Case, D. A. Automatic Atom Type and Bond Type Perception in Molecular Mechanical Calculations J. Mol. Graph. Model. 2006, 25 (2) 247-260
54. Zheng, J. J.; Yeung, E. S. Mechanism of Microbial Aggregation During Capillary Electrophoresis Anal. Chem. 2003, 75 (4) 818-824
55. Agasti, S. S.; You, C. C.; Arumugam, P.; Rotello, V. M. Structural Control of the Monolayer Stability of Water-Soluble Gold Nanoparticles J. Mater. Chem. 2008, 18 (1) 70-73
56. Dougan, J. A.; Karlsson, C.; Smith, W. E.; Graham, D. Enhanced Oligonucleotide-Nanoparticle Conjugate Stability Using Thioctic Acid Modified Oligonucleotides Nucleic Acids Res. 2007, 35 (11) 3668-3675
57. Meister, A. Glutathione Metabolism and Its Selective Modification J. Biol. Chem. 1988, 263 (33) 17205-17208
58. Petrovykh, D. Y.; Kimura-Suda, H.; Opdahl, A.; Richter, L. J.; Tarlov, M. J.; Whitman, L. J. Alkanethiols on Platinum: Multicomponent Self-Assembled Monolayers Langmuir 2006, 22 (6) 2578-2587
59. Petrovykh, D. Y.; Sullivan, J. M.; Whitman, L. J. Quantification of Discrete Oxide and Sulfur Layers on Sulfur-Passivated InAs by XPS Surf. Interface Anal. 2005, 37 (11) 989-997
60. Widrig, C. A.; Alves, C. A.; Porter, M. D. Scanning Tunneling Microscopy of Ethanethiolate and n-Octadecanethiolate Monolayers Spontaneously Adsorbed at Gold Surfaces J. Am. Chem. Soc. 1991, 113 (8) 2805-2810
61. Vance, A. L.; Willey, T. M.; Nelson, A. J.; van Buuren, T.; Bostedt, C.; Terminello, L. J.; Fox, G. A.; Engelhard, M.; Baer, D. XAS and XPS Characterization of Monolayers Derived from a Dithiol and Structurally Related Disulfide-Containing Polyamides Langmuir 2002, 18 (21) 8123-8128
62. Jang, Y. H.; Goddard, W. A. Electron Transport through Cyclic Disulfide Molecular Junctions with Two Different Adsorption States at the Contact: A Density Functional Theory Study J. Phys. Chem. C 2008, 112 (23) 8715-8720
63. Fenter, P.; Eberhardt, A.; Eisenberger, P. Self-Assembly of n-Alkyl Thiols as Disulfides on Au(111) Science 1994, 266 (5188) 1216-1218