Design of a multi-dopamine-modified polymer ligand optimally suited for interfacing magnetic nanoparticles with biological systems

Langmuir

Volumn 30, Issue 21, 2014, Pages 6197-6208

  Wang, Wentao ^a   Ji, Xin ^a   Na, Hyon Bin ^a,c   Safi, Malak ^a   Smith, Alexandra ^b   Palui, Goutam ^a   Perez, J Manuel ^b   Mattoussi, Hedi ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CENTRAL FLORIDA   (United States)

^c Myong Ji University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; BIOLOGICAL SYSTEMS; HYDROPHILICITY; MALEIC ANHYDRIDE; NANOPARTICLES; NEUROPHYSIOLOGY; POLYETHYLENE GLYCOLS; POLYMERS;

AMPHIPHILIC POLYMERS; COLLOIDAL STABILITY; HYDROPHILIC NANOPARTICLES; IRON OXIDE NANOPARTICLE; MAGNETIC NANO-PARTICLES; NUCLEOPHILIC ADDITIONS; ONE-STEP REACTIONS; SURFACE FUNCTIONALIZING;

LIGANDS;

AMIDE; AMINE; COLLOID; CONTRAST MEDIUM; ELECTROLYTE; FERRIC ION; FERRIC OXIDE; LIGAND; MALEIC ANHYDRIDE; METAL NANOPARTICLE; NANOPARTICLE; POLYMER; POTASSIUM IODIDE;

CELL SURVIVAL; CHEMISTRY; COLLOID; FLUORESCENCE MICROSCOPY; HELA CELL LINE; HUMAN; HYDRODYNAMICS; LIGHT; MAGNETISM; NUCLEAR MAGNETIC RESONANCE IMAGING; PH; RADIATION SCATTERING;

AMIDES; AMINES; CELL SURVIVAL; COLLOIDS; CONTRAST MEDIA; ELECTROLYTES; FERRIC COMPOUNDS; HELA CELLS; HUMANS; HYDRODYNAMICS; HYDROGEN-ION CONCENTRATION; LIGANDS; LIGHT; MAGNETIC RESONANCE IMAGING; MAGNETICS; MALEIC ANHYDRIDES; METAL NANOPARTICLES; MICROSCOPY, FLUORESCENCE; NANOPARTICLES; POLYMERS; POTASSIUM IODIDE; SCATTERING, RADIATION;

EID: 84901830340     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la500974r     Document Type: Article

References (55)

1. Lewin, M.; Carlesso, N.; Tung, C. H.; Tang, X. W.; Cory, D.; Scadden, D. T.; Weissleder, R. Tat peptide-derivatized magnetic nanoparticles allow in vivo tracking and recovery of progenitor cells Nat. Biotechnol. 2000, 18, 410-414
2. Gupta, A. K.; Gupta, M. Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications Biomaterials 2005, 26, 3995-4021
3. Lee, J. H.; Huh, Y. M.; Jun, Y.; Seo, J.; Jang, J.; Song, H. T.; Kim, S.; Cho, E. J.; Yoon, H. G.; Suh, J. S.; Cheon, J. Artificially engineered magnetic nanoparticles for ultra-sensitive molecular imaging Nat. Med. 2007, 13, 95-99
4. Jun, Y. W.; Lee, J. H.; Cheon, J. Chemical design of nanoparticle probes for high-performance magnetic resonance imaging Angew. Chem., Int. Ed. 2008, 47, 5122-5135
5. Mattoussi, H.; Cheon, J. Inorganic Nanoprobes for Biological Sensing and Imaging; Artech House: Boston, 2009.
6. Kim, J.; Piao, Y.; Hyeon, T. Multifunctional nanostructured materials for multimodal imaging, and simultaneous imaging and therapy Chem. Soc. Rev. 2009, 38, 372-390
7. Frey, N. A.; Peng, S.; Cheng, K.; Sun, S. Magnetic nanoparticles: synthesis, functionalization, and applications in bioimaging and magnetic energy storage Chem. Soc. Rev. 2009, 38, 2532-2542
8. Perez, J. M.; Josephson, L.; O'Loughlin, T.; Hogemann, D.; Weissleder, R. Magnetic relaxation switches capable of sensing molecular interactions Nat. Biotechnol. 2002, 20, 816-820
9. Xu, C. J.; Xu, K. M.; Gu, H. W.; Zheng, R. K.; Liu, H.; Zhang, X. X.; Guo, Z. H.; Xu, B. Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles J. Am. Chem. Soc. 2004, 126, 9938-9939
10. Nasongkla, N.; Bey, E.; Ren, J. M.; Ai, H.; Khemtong, C.; Guthi, J. S.; Chin, S. F.; Sherry, A. D.; Boothman, D. A.; Gao, J. M. Multifunctional polymeric micelles as cancer-targeted, MRI-ultrasensitive drug delivery systems Nano Lett. 2006, 6, 2427-2430
11. Medarova, Z.; Pham, W.; Farrar, C.; Petkova, V.; Moore, A. In vivo imaging of siRNA delivery and silencing in tumors Nat. Med. 2007, 13, 372-377
12. El-Boubbou, K.; Zhu, D. C.; Vasileiou, C.; Borhan, B.; Prosperi, D.; Li, W.; Huang, X. F. Magnetic Glyco-Nanoparticles: A Tool To Detect, Differentiate, and Unlock the Glyco-Codes of Cancer via Magnetic Resonance Imaging J. Am. Chem. Soc. 2010, 132, 4490-4499
13. Santra, S.; Kaittanis, C.; Grimm, J.; Perez, J. M. Drug/Dye-Loaded, Multifunctional Iron Oxide Nanoparticles for Combined Targeted Cancer Therapy and Dual Optical/Magnetic Resonance Imaging Small 2009, 5, 1862-1868
14. Rockenberger, J.; Scher, E. C.; Alivisatos, A. P. A new nonhydrolytic single-precursor approach to surfactant-capped nanocrystals of transition metal oxides J. Am. Chem. Soc. 1999, 121, 11595-11596
15. Park, J.; An, K. J.; Hwang, Y. S.; Park, J. G.; Noh, H. J.; Kim, J. Y.; Park, J. H.; Hwang, N. M.; Hyeon, T. Ultra-large-scale syntheses of monodisperse nanocrystals Nat. Mater. 2004, 3, 891-895
16. Sun, S. H.; Zeng, H.; Robinson, D. B.; Raoux, S.; Rice, P. M.; Wang, S. X.; Li, G. X. Monodisperse MFe2O4 (M = Fe, Co, Mn) nanoparticles J. Am. Chem. Soc. 2004, 126, 273-279
17. Yu, W. W.; Falkner, J. C.; Yavuz, C. T.; Colvin, V. L. Synthesis of monodisperse iron oxide nanocrystals by thermal decomposition of iron carboxylate salts Chem. Commun. 2004, 20, 2306-2307
18. Jun, Y. W.; Huh, Y. M.; Choi, J. S.; Lee, J. H.; Song, H. T.; Kim, S.; Yoon, S.; Kim, K. S.; Shin, J. S.; Suh, J. S.; Cheon, J. Nanoscale size effect of magnetic nanocrystals and their utilization for cancer diagnosis via magnetic resonance imaging J. Am. Chem. Soc. 2005, 127, 5732-5733
19. Zhang, F.; Lees, E.; Amin, F.; Gil, P. R.; Yang, F.; Mulvaney, P.; Parak, W. J. Polymer-Coated Nanoparticles: A Universal Tool for Biolabelling Experiments Small 2011, 7, 3113-3127
20. Mattoussi, H.; Palui, G.; Na, H. B. Luminescent quantum dots as platforms for probing in vitro and in vivo biological processes Adv. Drug Delivery Rev. 2012, 64, 138-166
21. Mout, R.; Moyano, D. F.; Rana, S.; Rotello, V. M. Surface functionalization of nanoparticles for nanomedicine Chem. Soc. Rev. 2012, 41, 2539-2544
22. Ling, D.; Hyeon, T. Chemical design of biocompatible iron oxide nanoparticles for medical applications Small 2013, 9, 1450-66
23. Kim, B. S.; Qiu, J. M.; Wang, J. P.; Taton, T. A. Magnetomicelles: Composite nanostructures from magnetic nanoparticles and cross-linked amphiphilic block copolymers Nano Lett. 2005, 5, 1987-1991
24. Tromsdorf, U. I.; Bigall, N. C.; Kaul, M. G.; Bruns, O. T.; Nikolic, M. S.; Mollwitz, B.; Sperling, R. A.; Reimer, R.; Hohenberg, H.; Parak, W. J.; Forster, S.; Beisiegel, U.; Adam, G.; Weller, H. Size and surface effects on the MRI relaxivity of manganese ferrite nanoparticle contrast agents Nano Lett. 2007, 7, 2422-2427
25. Yu, W. W.; Chang, E.; Falkner, J. C.; Zhang, J. Y.; Al-Somali, A. M.; Sayes, C. M.; Johns, J.; Drezek, R.; Colvin, V. L. Forming biocompatible and nonaggregated nanocrystals in water using amphiphilic polymers J. Am. Chem. Soc. 2007, 129, 2871-2879
26. Lin, C. A.; Sperling, R. A.; Li, J. K.; Yang, T. Y.; Li, P. Y.; Zanella, M.; Chang, W. H.; Parak, W. J. Design of an amphiphilic polymer for nanoparticle coating and functionalization Small 2008, 4, 334-341
27. Pellegrino, T.; Manna, L.; Kudera, S.; Liedl, T.; Koktysh, D.; Rogach, A. L.; Keller, S.; Radler, J.; Natile, G.; Parak, W. J. Hydrophobic nanocrystals coated with an amphiphilic polymer shell: A general route to water soluble nanocrystals Nano Lett. 2004, 4, 703-707
28. Lees, E. E.; Nguyen, T. L.; Clayton, A. H. A.; Muir, B. W.; Mulvaney, P. The Preparation of Colloidally Stable, Water-Soluble, Biocompatible, Semiconductor Nanocrystals with a Small Hydrodynamic Diameter ACS Nano 2009, 3, 1121-1128
29. Wu, X. Y.; Liu, H. J.; Liu, J. Q.; Haley, K. N.; Treadway, J. A.; Larson, J. P.; Ge, N. F.; Peale, F.; Bruchez, M. P. Immunofluorescent labeling of cancer marker Her2 and other cellular targets with semiconductor quantum dots Nat. Biotechnol. 2003, 21, 41-46
30. Mikhaylov, G.; Mikac, U.; Magaeva, A. A.; Itin, V. I.; Naiden, E. P.; Psakhye, I.; Babes, L.; Reinheckel, T.; Peters, C.; Zeiser, R.; Bogyo, M.; Turk, V.; Psakhye, S. G.; Turk, B.; Vasiljeva, O. Ferri-liposomes as an MRI-visible drug-delivery system for targeting tumours and their microenvironment Nat. Nanotechnol. 2011, 6, 594-602
31. Boyer, C.; Whittaker, M. R.; Bulmus, V.; Liu, J. Q.; Davis, T. P. The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications NPG Asia Mater. 2010, 2, 23-30
32. Xie, J.; Xu, C. J.; Xu, Z. C.; Hou, Y. L.; Young, K. L.; Wang, S. X.; Pourmond, N.; Sun, S. H. Linking hydrophilic macromolecules to monodisperse magnetite (Fe3O4) nanoparticles via trichloro-s-triazine Chem. Mater. 2006, 18, 5401-5403
33. Amstad, E.; Gillich, T.; Bilecka, I.; Textor, M.; Reimhult, E. Ultrastable Iron Oxide Nanoparticle Colloidal Suspensions Using Dispersants with Catechol-Derived Anchor Groups Nano Lett. 2009, 9, 4042-4048
34. Wei, H.; Insin, N.; Lee, J.; Han, H. S.; Cordero, J. M.; Liu, W. H.; Bawendi, M. G. Compact Zwitterion-Coated Iron Oxide Nanoparticles for Biological Applications Nano Lett. 2012, 12, 22-25
35. Zhang, T. R.; Ge, J. P.; Hu, Y. X.; Yin, Y. D. A general approach for transferring hydrophobic nanocrystals into water Nano Lett. 2007, 7, 3203-3207
36. 3 nanoparticles by using a multifunctional polymeric linker Small 2007, 3, 1374-1378
37. Liong, M.; Shao, H.; Haun, J. B.; Lee, H.; Weissleder, R. Carboxymethylated polyvinyl alcohol stabilizes doped ferrofluids for biological applications Adv. Mater. 2010, 22, 5168-5172
38. Stewart, M. H.; Susumu, K.; Mei, B. C.; Medintz, I. L.; Delehanty, J. B.; Blanco-Canosa, J. B.; Dawson, P. E.; Mattoussi, H. Multidentate Poly(ethylene glycol) Ligands Provide Colloidal Stability to Semiconductor and Metallic Nanocrystals in Extreme Conditions J. Am. Chem. Soc. 2010, 132, 9804-9813
39. Ling, D.; Park, W.; Park, Y. I.; Lee, N.; Li, F.; Song, C.; Yang, S. G.; Choi, S. H.; Na, K.; Hyeon, T. Multiple-Interaction Ligands Inspired by Mussel Adhesive Protein: Synthesis of Highly Stable and Biocompatible Nanoparticles Angew. Chem., Int. Ed. 2011, 50, 11360-11365
40. Na, H. B.; Palui, G.; Rosenberg, J. T.; Ji, X.; Grant, S. C.; Mattoussi, H. Multidentate catechol-based polyethylene glycol oligomers provide enhanced stability and biocompatibility to iron oxide nanoparticles ACS Nano 2012, 6, 389-399
41. Uyeda, H. T.; Medintz, I. L.; Jaiswal, J. K.; Simon, S. M.; Mattoussi, H. Synthesis of compact multidentate ligands to prepare stable hydrophilic quantum dot fluorophores J. Am. Chem. Soc. 2005, 127, 3870-3878
42. Nikolic, M. S.; Krack, M.; Aleksandrovic, V.; Kornowski, A.; Forster, S.; Weller, H. Tailor-made ligands for biocompatible nanoparticles Angew. Chem., Int. Ed. 2006, 45, 6577-6580
43. Pons, T.; Uyeda, H. T.; Medintz, I. L.; Mattoussi, H. Hydrodynamic dimensions, electrophoretic mobility, and stability of hydrophilic quantum dots J. Phys. Chem. B 2006, 110, 20308-20316
44. Lee, N.; Hyeon, T. Designed synthesis of uniformly sized iron oxide nanoparticles for efficient magnetic resonance imaging contrast agents Chem. Soc. Rev. 2012, 41, 2575-2589
45. Huang, J.; Bu, L. H.; Xie, J.; Chen, K.; Cheng, Z.; Li, X. G.; Chen, X. Y. Effects of Nanoparticle Size on Cellular Uptake and Liver MRI with Polyvinylpyrrolidone-Coated Iron Oxide Nanoparticles ACS Nano 2010, 4, 7151-7160
46. 4 nanoparticles for reduced non-specific uptake by macrophage cells Adv. Mater. 2007, 19, 3163-3166
47. Mirkin, C. A.; Letsinger, R. L.; Mucic, R. C.; Storhoff, J. J. A DNA-based method for rationally assembling nanoparticles into macroscopic materials Nature 1996, 382, 607-609
48. Clapp, A. R.; Medintz, I. L.; Mauro, J. M.; Fisher, B. R.; Bawendi, M. G.; Mattoussi, H. Fluorescence resonance energy transfer between quantum dot donors and dye-labeled protein acceptors J. Am. Chem. Soc. 2004, 126, 301-310
49. Mattoussi, H.; Mauro, J. M.; Goldman, E. R.; Anderson, G. P.; Sundar, V. C.; Mikulec, F. V.; Bawendi, M. G. Self-assembly of CdSe-ZnS quantum dot bioconjugates using an engineered recombinant protein J. Am. Chem. Soc. 2000, 122, 12142-12150
50. 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, 1904-2074
51. Guardia, P.; Di Corato, R.; Lartigue, L.; Wilhelm, C.; Espinosa, A.; Garcia-Hernandez, M.; Gazeau, F.; Manna, L.; Pellegrino, T. Water-Soluble Iron Oxide Nanocubes with High Values of Specific Absorption Rate for Cancer Cell Hyperthermia Treatment ACS Nano 2012, 6, 3080-3091
52. Piao, Y.; Jin, Z.; Lee, D.; Lee, H. J.; Na, H. B.; Hyeon, T.; Oh, M. K.; Kim, J.; Kim, H. S. Sensitive and high-fidelity electrochemical immunoassay using carbon nanotubes coated with enzymes and magnetic nanoparticles Biosens. Bioelectron. 2011, 26, 3192-3199
53. Jun, Y. W.; Seo, J. W.; Cheon, A. Nanoscaling laws of magnetic nanoparticles and their applicabilities in biomedical sciences Acc. Chem. Res. 2008, 41, 179-189
54. Sandiford, L.; Phinikaridou, A.; Protti, A.; Meszaros, L. K.; Cui, X. J.; Yan, Y.; Frodsham, G.; Williamson, P. A.; Gaddum, N.; Botnar, R. M.; Blower, P. J.; Green, M. A.; de Rosales, R. T. M. Bisphosphonate-Anchored PEGylation and Radiolabeling of Superparamagnetic Iron Oxide: Long-Circulating Nanoparticles for in Vivo Multimodal (T1MRI-SPECT) Imaging ACS Nano 2013, 7, 500-512
55. Mattoussi, H.; Karasz, F. E.; Langley, K. H. Electrostatic and Screening Effects on the Dynamic Aspects of Polyelectrolyte Solutions J. Chem. Phys. 1990, 93, 3593-3603