PEGylated gold nanoparticles conjugated to monoclonal F19 antibodies as targeted labeling agents for human pancreatic carcinoma tissue

ACS Nano

Volumn 2, Issue 11, 2008, Pages 2263-2272

  Eck, Wolfgang ^a,e   Craig, Gary ^b   Sigdel, Aruna ^b   Ritter, Gerd ^c   Old, Lloyd J ^c   Tang, Laura ^d   Brennan, Murray F ^d   Allen, Peter J ^d   Mason, Michael D ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b University of Maine   (United States)

^c LUDWIG INSTITUTE FOR CANCER RESEARCH   (Australia)

^d MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^e JACKSON LABORATORY   (United States)

Author keywords

Darkfield microscopy; F19 monoclonal antibody; Heterobifunctional polyethylene glycol; Pancreatic cancer; Targeted gold nanoparticles; Tissue labeling

Indexed keywords

AGGLOMERATION; ALLERGIES; BIOMOLECULES; CHROMATOGRAPHIC ANALYSIS; ETHYLENE GLYCOL; GLYCOLS; GOLD; LABELING; MERGERS AND ACQUISITIONS; MONOCLONAL ANTIBODIES; NANOPARTICLES; ORGANIC POLYMERS; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; SIZE EXCLUSION CHROMATOGRAPHY; SURFACE PLASMON RESONANCE; THERMOPLASTICS; TISSUE; TUMORS;

DARKFIELD MICROSCOPY; F19 MONOCLONAL ANTIBODY; HETEROBIFUNCTIONAL POLYETHYLENE GLYCOL; PANCREATIC CANCER; TARGETED GOLD NANOPARTICLES;

ANTIBODIES;

GOLD; LIGAND; MACROGOL DERIVATIVE; METAL NANOPARTICLE; MONOCLONAL ANTIBODY;

ARTICLE; CARCINOMA; CHEMISTRY; CONFORMATION; HUMAN; LIGHT; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; NANOTECHNOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PANCREAS TUMOR; PATHOLOGY; RADIATION SCATTERING; TRANSMISSION ELECTRON MICROSCOPY;

ANTIBODIES, MONOCLONAL; CARCINOMA; GOLD; HUMANS; LIGANDS; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; METAL NANOPARTICLES; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR CONFORMATION; NANOTECHNOLOGY; PANCREATIC NEOPLASMS; POLYETHYLENE GLYCOLS; SCATTERING, RADIATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 58049220470     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn800429d     Document Type: Article

References (66)

1. Alivisatos, P. A.; Gu, W.; Larabell, C. Quantum Dots as Cellular Probes. Annu. Rev. Biomed. Eng. 2005, 7, 55-76.
2. Shiraishi, Y.; Maeda, K.; Yoshikawa, H.; Xu, J.; Toshima, N.; Kobayashi, S. Frequency Modulation Response of a Liquid-Crystal Electro-Optic Device Doped with Nanoparticles. Appl. Phys. Lett. 2002, 81, 2845-2847.
3. Law, M.; Greene, L. E.; Johnson, J. C.; Saykally, R.; Yang, P. Nanowire Dye-Sensitized Solar Cells. Nat. Mater. 2005, 4, 455-459.
4. Fuller, S. B.; Wilhelm, E. J.; Jacobson, J. M. Ink-Jet Printed Nanoparticle Microelectromechanical Systems. Microelectromech. Syst. 2002, 11, 54-60.
5. Carotenuto, G.; Pepe, G. P.; Nicolais, L. Preparation and Characterization of Nano-Sized Ag/PVP Composites for Optical Applications. Eur. Phys. J. B 2000, 16, 11-17.
6. Lo, C. T.; Chou, K. S.; Chin, W. K. Effects of Mixing Procedures on the Volume Fraction of Silver Particles in Conductive Adhesives. Adhes. Sci. Technol. 2001, 15, 783-792.
7. Mulvaney, S. P,; Musick, M. D.; Kearting, C. D.; Natan, M. J. Glass-Coated, Analyte-Tagged Nanoparticles: A New Tagging System Based an Detection with Surface-Enhanced Raman Scattering. Langmuir 2003, 19, 4784-4790.
8. Hughes, D. Immunogold Probes in Light Microscopy. In Methods in Molecular Biology; Burns, R., Ed.; Humana Press: Totowa, NJ, 2005; pp 173-192.
9. Pradhan, N.; Pal, A.; Pal, T. Silver Nanoparticle Catalyzed Reduction of Aromatic Nitro Compounds. Colloids Surf., A 2002, 196, 247-257.
10. Maxwell, D. J.; Taylor, J. R.; Nie, S. Self-Assembled Nanoparticle Probes for Recognition and Detection of Biomolecules. J. Am. Chem. Soc. 2002, 124, 9606-9612.
11. Salata, O. Applications of Nanoparticles in Biology and Medicine. J. Nonobiotechnol. 2004, 2, 3-8.
12. Tamm, E. P.; Lover, E. M.; Faria, S. C.; Evans, D. B.; Wolff, R. A.; Charnsangavej, C. Retrospective Analysis of Dual-Phase MDCT and Follow-up EUS/EUS-FNA in the Diagnosis of Pancreatic Cancer. Abdom. Imaging 2007, 32, 660-667.
13. Kulig, J.; Popiela, T.; Zajac, A.; Klek, S.; Kolodziejczyk, P. The Value of Imaging Techniques in the Staging of Pancreatic Cancer. Surg. Endoc. 2005, 19, 361-365.
14. White, R.; Winston, C.; Gonen, M.; D'Angelica, M.; Jarnagin, W.; Conlon, K.; Fong, Y.; Brennan, M.; Allen, P. Current Utility of Staging Laparoscopy for Pancreatic and Peripancreatic Neoplasms. J. Am. Coll. Surgeons 2007, 9, 445-450.
15. Conlon, K. C.; Dougherty, E.; Klimstra, D. S.; Coit, D. G.; Turnbull, A. D.; Brennan, M. F. The Value of Minimal Access Surgery in the Staging of Patients with Potentially Resectable Peripancreatic Malignancy. Ann. Surg. 1996, 223, 134-140.
16. Camacho, D.; Reichenbach, D.; Duerr, G. D.; Venema, T. L.; Sweeney, J. F.; Fisher, W. E. Value of Laparoscopy in the Staging of Pancreatic Cancer. J. Pancreas 2005, 6, 552-561.
17. Ferrone, C. R.; Haas, B.; Tang, L.; Coit, D. G.; Fong, Y.; Brennan, M. F.; Allen, P. J. The Influence of Positive Peritoneal Cytology ah Survival in Patients with Pancreatic Adenocarcinoma. J. Gastrointest. Surg. 2006, 10, 1347-1353.
18. Hainfeld, J. F. S.; D. N., Focella, T. M.; Smilowitz, H. M. Gold Nanoparticles: A New X-Ray Contrast Agent. Br. J. Radiol. 2006, 79, 248-253.
19. Kim, D. P.; S.; Lee, J. H.; Jeong, Y. Y.; Jon, S. Antibiofouling Polymer-Coated Gold Nanoparticles as a Contrast Agent for in Vivo X-Ray Computed Tomography Imaging. J. Am. Chem. Soc. 2007, 129, 7661-7665.
20. El-Sayed, I. H.; Huang, X.; El-Sayed, M. A. Surface Plasmon Resonance Scattering and Absorption of Anti-EGFR Antibody Conjugated Gold Nanoparticles in Cancer Diagnostics: Applications in Oral Cancer. Nano Lett. 2005, 5, 829-834.
21. Curry, A.; Hwang, W. L.; Wax, A. Epi-Illumination through the Microscope Objective Applied to Darkfield Imaging and Microspectroscopy of Nanoparticle Interaction with Cells in Culture. Opt. Express 2006, 14, 6535-6542.
22. Zheng, J.; Zhang, C.; Dickson, R., M. Highly Fluorescent, Water-Soluble, Size- Tunable Gold Quantum Dots. Phys. Rev. Lett. 2004, 93, 077402-1-077402-4.
23. Kirchner, C.; Liedl, T.; Kudera, S.; Pellegrino, T.; Javier, A. M.; Gaub, H. R.; Stoelzle, S.; Fertig, N.; Parak, W. J. Cytotoxicity of Colloidal CdSe and CdSe/ZnS Nanoparticles. Nano Lett. 2005, 5, 331-338.
24. Hermann, R.; Walther, P.; Mueller, M. Immunogold Labeling in Scanning Electron Microscopy. Histochem. Cell Biol. 1996, 106, 31-39.
25. Wooding, F. B. P.; Kendall, M. D. Immunogold Methods for Electron Microscopy. Methods. Immunol. Anal. 1993, 3, 314-337.
26. Verkleij, A. J.; Koster, A. J.; Muller, W. H.; Humbel, B. M. Immuno-Gold Labeling in Transmission Electron Microscopy. NATO ASI Ser. A, Life Sci. 1999, 309, 339-356.
27. Hainfeld, J. F.; Powell, R. D.; New Frontiers in Gold Labeling. J. Histochem. Cytochem. 2000, 48, 471-480.
28. Herrwerth, S.; Rosendahl, T.; Feng, C.; Fick, J.; Eck, W.; Himmelhaus, M.; Dahint, R.; Grunze, M. Covalent Coupling of Antibodies to Self-Assembled Monolayers of Carboxy-Functionalized Poly(Ethylene Glycol): Protein Resistance and Specific Binding of Biomolecules. Langmuir 2003, 19, 1880-1897.
29. Otsuka, H.; Akiyama, Y.; Nagasaki, Y.; Kataoka, K. Quantitative and Reversible Lectin-Induced Association of Gold Nanoparticles Modified with α-Lactosyl-ω-Mercapto-Poly(Ethylene Glycol). J. Am. Chem. Soc. 2001, 123, 8226-8230.
30. Otsuka, H.; Nagasaki, Y.; Kataoka, K. PEGylated Nanoparticles for Biological and Pharmaceutical Applications. Adv. Drug Delivery Rev. 2003, 55, 403-419.
31. Kim, J.; Park, S.; Lee, J. E.; Jin, S. M.; Lee, J. H.; Lee, I. S.; Yang, I,; Kim, J,; Kim, S, K.; Cho, M.; et al. Designed Fabrication of Multifunctional Magnetic Gold Nanoshells and Their Application to Magnetic Resonance Imaging and Photothermal Therapy. Angew. Chem., Int. Ed. 2006, 45, 7754-7758.
32. Garcia, B.; Salome, M.; Lemelle, L.; Bridot, J.-L.; Gillet, P.; Perriat, P.; Roux, S.; Tillement, O. Sulfur K-Edge XANES Study of Dihydrolipoic Acid Capped Gold Nanoparticles: Dihydrolipoic Acid is Bound by Both Sulfur Ends. Chem. Commun. 2005, 369-371.
33. Pierrat, S.; Zins, I.; Breivogel, A.; Soennichsen, C. Self-Assembly of Small Gold Colloids with Functionalized Gold Nanorods. Nano Lett. 2007, 7, 259-263.
34. Shenoy, D.; Fu, W.; Li, J.; Crasto, C.; Jones, G.; DiMarzio, C.; Sridhar, S.; Amiji, M. Surface Functionalization of Gold Nanoparticles Using Hetero-Bifunctional Poly(Ethylene Glycol) Spacer for Intracellular Tracking and Delivery. Int. J. Nanomedicine 2006, 1, 51-57.
35. Sperling, R. A.; Pellegrino, T.; Li, J. K.; Chang, W. H.; Parak, W. J. Electrophoretic Separation of Nanoparticles with a Discrete Number of Functional Groups. Adv. Funct. Mater. 2006, 16, 943-948.
36. Liu, Y.; Shipton, M. K.; Ryan, J.; Kaufman, E. D.; Franzen, S.; Feldheim, D. L. Synthesis, Stability, and Cellular Internalization of Gold Nanoparticles Containing Mixed Peptide-Poly(Ethylene Glycol) Monolayers. Anal Chem. 2007, 79, 2221-2229.
37. Gref, R.; Couvreur, P. Stealth and Biomimetic Core-Corona Nanoparticles. In Encyclopedia of Nonoscience and Nanotechnology; Nalwa, H. S., Ed.; American Scientific Publishers: Stevenson Ranch, CA, 2004; pp 83-94.
38. Dixit, V.; Van den Bossche, J.; Sherman, D. M.; Thompson, D. H.; Andres, R. P. Synthesis and Grafting of Thioctic Acid-PEG-Folate Conjugates onto Au Nanoparticles for Selective Targeting of Folate Receptor-Positive Tumor Cells. Bioconjugate Chem. 2006, 17, 603-609.
39. Liao, H.; Hafner, J. H. Gold Nanorod Bioconjugates. Chem. Mater. 2005, 17, 4636-4641.
40. Owens, D. E.; Peppas, N. A. Opsonization, Biodistribution, and Pharmacokinetics of Polymeric Nanoparticles. Int. J. Pharm. 2006, 307, 93-102.
41. Sun, C.; Sze, R.; Zhang, M. Folic Acid-PEG Conjugated Superparamagnetic Nanoparticles for Targeted Cellular Uptake and Detection by MRI. J. Biomed. Mater. Res., Port A 2006, 78A, 550-557.
42. Abad, J. M,; Mertens, S. F. L.; Pita, M,; Fernandez, V. M.; Schiffrin, D. J. Functionalization of Thioctic Acid-Capped Gold Nanoparticles for Specific Immobilization of Histidine-Tagged Proteins. J. Am. Chem. Soc. 2005, 127, 5689-5694.
43. Kumar, S.; Aaron, J.; Sokolov, K. Directional Conjugation of Antibodies to Nanoparticles for Synthesis of Multiplexed Optical Contrast Agents with Both Delivery and Targeting Moieties. Nat. Protoc. 2008, 3, 314-320.
44. Qian, X.; Peng, X.-H.; Ansari, D. O.; Yin-Goen, Q.; Chen, G. Z.; Shin, D. M.; Yang, L.; Young, A. N.; Wang, M. D.; Nie, S. In Vivo Tumor Targeting and Spectroscopic Detection with Surface-Enhanced Raman Nanoparticle Tags. Nat. Biotechnol. 2008, 26, 83-90.
45. Lin, S.-Y.; Tsai, Y.-T.; Chen, C.-C.; Lin, C.-M.; Chen, C.-h. Two-Step Functionalization of Neutral and Positively Charged Thiols onto Citrate-Stabilized Au Nanoparticles. J. Phys. Chem. B 2004, 108, 2134-2139.
46. Wang, L., Shi, X.; Kariuki, N. N.; Schadt, M.; Wang, G. R.; Rendeng, Q.; Choi, J.; Luo, J.; Lu, S.; Zhong, C. J. Array of Molecularly Mediated Thin Film Assemblies of Nanoparticles: Correlation of Vapor Sensing with Interparticle Spatial Properties. J. Am. Chem. Soc. 2007, 129, 2161-2170.
47. Yokoyama, M.; Okano, T.; Sakurai, Y.; Kikuchi, A.; Ohsako, N.; Nagasaki, Y.; Kataoka, K. Synthesis of Poly(Ethylene Oxide) with Heterobifunctional Reactive Groups at its Terminals by an Anionic Initiator. Bioconjugate Chem. 1992, 3, 275-276.
48. Akiyama, Y.; Otsuka, H.; Nagasaki, Y.; Kato, M.; Kataoka, K. Selective Synthesis of Heterobifunctional Poly(Ethylene Glycol) Derivatives Containing Both Mercapto and Acetal Terminals. Bioconjugate Chem. 2000, 11, 947-950.
49. Park, J. E.; Lenter, M. C.; Zimmermann, R. N.; Garin-Chesa, P.; Old, L. J.; Rettig, W. J. Fibroblast Activation Protein, a Dual Specificity Serine Protease Expressed in Reactive Human Tumor Stromal Fibroblasts. J. Biol. Chem. 1999, 274, 36505-36512.
50. Rettig, W. J.; Garin-Chesa, P.; Healey, J. H.; Su, S. L.; Jaffe, E. A.; Old, L. J. Identification of Endosialin, a Cell Surface Glycoprotein of Vascular Endothelial Cells in Human Cancer. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10832-10836.
51. Scanlan, M. J.; Raj, B. K.; Calvo, B.; Garin-Chesa, P.; Sanz-Moncasi, M. P.; Healey, J. H.; Old, L. J.; Rettig, W. J. Molecular Cloning of Fibroblast Activation Protein Alpha, a Member of the Serine Protease Family Selectively Expressed in Stromal Fibroblasts of Epithelial Cancers. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 5657-5661.
52. Scott, A. M.; Wiseman, G.; Welt, S.; Adjei, A.; Lee, F. T.; Hopkins, W.; Divgi, C. R.; Nahson, L. H.; Mitchell, P.; Gansen, D. N.; et al. Phase I Dose-Escalation Study of Sibrotuzumab in Patients with Advanced or Metastatic Fibroblast Activation Protein-Positive Cancer. Clin. Cancer Res. 2003, 9, 1639-1647.
53. Grabar, K. C.; Freeman, R. G.; Hommer, M. B.; Natan, M. J. Preparation and Characterization of Au Colloid Monolayers. Anal. Chem. 1995, 67, 735-743.
54. Schneider, G.; Decher, G.; Nerambourg, N.; Praho, R.; Werts, M. H. V.; Blanchard-Desce, M. Distance-Dependent Fluorescence Quenching on Gold Nanoparticles Ensheathed with Layer-by-Layer Assembled Polyelectrolytes. Nano Lett. 2006, 6, 530-536.
55. Dulkeith, E.; Ringler, M.; Klar, T. A.; Feldmann, J.; Javier, A. M.; Parak, W. J. Gold Nanoparticles Quench Fluorescence by Phase Induced Radiative Rate Suppression. Nano Lett. 2005, 5, 585-589.
56. Garin-Chesa, P.; Old, L. J.; Rettig, W. J. Cell Surface Glycoprotein of Reactive Stromal Fibroblasts as a Potential Antibody Target in Human Epithelial Cancers. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 7235-7239.
57. Welt, S.; Divgi, C. R.; Scott, A. M.; Garin-Chesa, P.; Finn, R. D.; Graham, M.; Carswell, E. A.; Cohen, A.; Larson, S. M.; Old, L. J. Antibody Targeting in Metastatic Colon Cancer: A Phase I Study of Monoclonal Antibody F19 against a Cell-Surface Protein of Reactive Tumor Stromal Fibroblasts. J. Clin. Oncol. 1994, 12, 1193-1203.
58. Kumar, S.; Kortum, R. R. Optical Molecular Imaging Agents for Cancer Diagnostics and Therapeutics. Nanomedicine 2006, 1, 23-30.
59. El-Sayed, I. H.; Huang, X.; El-Sayed, M. A. Selective Laser Photo-Thermal Therapy of Epithelial Carcinoma Using Anti-EGFR Antibody Conjugated Gold Nanoparticles. Cancer Lett. 2006, 239, 129-135.
60. Huang, X.; El-Sayed, I. H.; Qian, W.; El-Sayed, M. A. Cancer Cells Assemble and Align Gold Nanorods Conjugated to Antibodies to Produce Highly Enhanced, Sharp, and Polarized Surface Raman Spectra: A Potential Cancer Diagnostic Marker. Nano Lett. 2007, 7, 1591-1597.
61. Loo, C.; Hirsch, L.; Lee, M.-H.; Chang, E.; West, J.; Halas, N.; Drezek, R. Gold Nanoshell Bioconjugates for Molecular Imaging in Living Cells. Opt. Lett. 2005, 30, 1012-1014.
62. Durr, N. J.; Larson, T.; Smith, D. K.; Korgel, B. A.; Sokolov, K., Ben-Yakar, A. Two-Photon Luminescence Imaging of Cancer Cells Using Molecularly Targeted Gold Nanorods. Nano Lett. 2007, 7, 941-945.
63. Mallidi, S.; Larson, T.; Aaron, J.; Sokolov, K.; Emelianov, S. Molecular Specific Optoacoustic Imaging with Plasmonic Nanoparticles. Opt. Express 2007, 15, 6583-6588.
64. Rahman, M.; Abd-El-Barr, M.; Mack, V.; Tkaczyk T.; Sokolov, K.; Richards-Kortum, R.; Descour, M. Optical Imaging of Cervical Pre-Cancers with Structured Illumination: An Integrated Approach. Gynecol. Oncol. 2005, 99, S112-S115.
65. Grabarek, Z.; Gergely, J. Zero-Length Crosslinking Procedure with the Use of Active Esters. Anal Biochem. 1990, 185, 131-135.
66. Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, CA, 1995.