Modular Fabrication of Polymer Brush Coated Magnetic Nanoparticles: Engineering the Interface for Targeted Cellular Imaging

ACS Applied Materials and Interfaces

Volumn 8, Issue 30, 2016, Pages 19813-19826

  Oz, Yavuz ^a   Arslan, Mehmet ^a   Gevrek, Tugce N ^a   Sanyal, Rana ^a   Sanyal, Amitav ^a  

^a BOGAZICI UNIVERSITY   (Turkey)

Author keywords

bioconjugation; click chemistry; functional coating; magnetic nanoparticle; polymer brush

Indexed keywords

CELL MEMBRANES; CHAINS; CHEMICAL MODIFICATION; COATED MATERIALS; DENDRIMERS; FREE RADICAL POLYMERIZATION; FUNCTIONAL MATERIALS; HYDROCARBONS; MAGNETISM; NANOPARTICLES; PEPTIDES; PLASTIC COATINGS; PROTECTIVE COATINGS;

BIO-CONJUGATION; CLICK CHEMISTRY; FUNCTIONAL COATING; MAGNETIC NANO-PARTICLES; POLYMER BRUSHES;

NANOMAGNETICS;

ALKYNE; AZIDE; MAGNETITE NANOPARTICLE; POLYMER;

CHEMISTRY; DIAGNOSTIC IMAGING; HUMAN; POLYMERIZATION; PROCEDURES; TUMOR CELL LINE;

ALKYNES; AZIDES; CELL LINE, TUMOR; DIAGNOSTIC IMAGING; HUMANS; MAGNETITE NANOPARTICLES; POLYMERIZATION; POLYMERS;

EID: 84982702404     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.6b04664     Document Type: Article

References (40)

1. Gao, J.; Gu, H.; Xu, B. Multifunctional Magnetic Nanoparticles: Design, Synthesis, and Biomedical Applications Acc. Chem. Res. 2009, 42, 1097-1107 10.1021/ar9000026
2. Laurent, S.; Forge, D.; Port, M.; Roch, A.; Robic, C.; Vander Elst, L.; Muller, R. N. Magnetic Iron Oxide Nanoparticles: Synthesis, Stabilization, Vectorization, Physicochemical Characterizations, and Biological Applications Chem. Rev. 2008, 108, 2064-2110 10.1021/cr068445e
3. 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 10.1039/C1CS15248C
4. Zhang, L.; Dong, W.-F.; Sun, H.-B. Multifunctional Superparamagnetic Iron Oxide Nanoparticles: Design, Synthesis and Biomedical Photonic Applications Nanoscale 2013, 5, 7664-7684 10.1039/c3nr01616a
5. Ling, D.; Lee, N.; Hyeon, T. Chemical Synthesis and Assembly of Uniformly Sized Iron Oxide Nanoparticles for Medical Applications Acc. Chem. Res. 2015, 48, 1276-1285 10.1021/acs.accounts.5b00038
6. Lee, H.; Lee, E.; Kim, D. K.; Jang, N. K.; Jeong, Y. Y.; Jon, S. Antibiofouling Polymer-Coated Superparamagnetic Iron Oxide Nanoparticles as Potential Magnetic Resonance Contrast Agents for in Vivo Cancer Imaging J. Am. Chem. Soc. 2006, 128, 7383-7389 10.1021/ja061529k
7. 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 10.1021/nn203735b
8. Turcheniuk, K.; Tarasevych, A. V.; Kukhar, V. P.; Boukherroub, R.; Szunerits, S. Recent Advances in Surface Chemistry Strategies for the Fabrication of Functional Iron Oxide Based Magnetic Nanoparticles Nanoscale 2013, 5, 10729-10752 10.1039/c3nr04131j
9. Lee, G. Y.; Qian, W. P.; Wang, L.; Wang, Y. A.; Staley, C. A.; Satpathy, M.; Nie, S.; Mao, H.; Yang, L. Theranostic Nanoparticles with Controlled Release of Gemcitabine for Targeted Therapy and MRI of Pancreatic Cancer ACS Nano 2013, 7, 2078-2089 10.1021/nn3043463
10. Huang, G.; Sun, Z.; Qin, H.; Zhao, L.; Xiong, Z.; Peng, X.; Ou, J.; Zou, H. Preparation of Hydrazine Functionalized Polymer Brushes Hybrid Magnetic Nanoparticles for Highly Specific Enrichment of Glycopeptides Analyst 2014, 139, 2199-2206 10.1039/c4an00076e
11. Shen, Y.; Guo, W.; Qi, L.; Qiao, J.; Wang, F.; Mao, L. Immobilization of Trypsin via Reactive Polymer Grafting from Magnetic Nanoparticles for Microwave-assisted Digestion J. Mater. Chem. B 2013, 1, 2260-2267 10.1039/c3tb20116c
12. Mu, X.; Qiao, J.; Qi, L.; Dong, P.; Ma, H. Poly(2-Vinyl-4,4-dimethylazlactone)-Functionalized Magnetic Nanoparticles as Carriers for Enzyme Immobilization and Its Application ACS Appl. Mater. Interfaces 2014, 6, 21346-21354 10.1021/am5063025
13. Chan, N.; Laprise-Pelletier, M.; Chevallier, P.; Bianchi, A.; Fortin, M.; Oh, J. K. Multidentate Block-Copolymer-Stabilized Ultrasmall Superparamagnetic Iron Oxide Nanoparticles with Enhanced Colloidal Stability for Magnetic Resonance Imaging Biomacromolecules 2014, 15, 2146-2156 10.1021/bm500311k
14. Lu, C.; Bhatt, L. R.; Jun, H. Y.; Park, S. H.; Chai, K. Y. Carboxyl-polyethylene Glycol-phosphoric Acid: A Ligand for Highly Stabilized Iron Oxide Nanoparticles J. Mater. Chem. 2012, 22, 19806-19811 10.1039/c2jm34327d
15. Das, M.; Bandyopadhyay, D.; Singh, R. P.; Harde, H.; Kumar, S.; Jain, S. Orthogonal Biofunctionalization of Magnetic Nanoparticles via "Clickable" Poly(ethylene glycol) Silanes: A "Universal Ligand" Strategy to Design Stealth and Target-specific Nanocarriers J. Mater. Chem. 2012, 22, 24652-24667 10.1039/c2jm34571d
16. 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 10.1021/nl902212q
17. Xu, C.; Xu, K.; Gu, H.; Zheng, R.; Liu, H.; Zhang, X.; Guo, Z.; 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 10.1021/ja0464802
18. Stone, R. C.; Qi, B.; Trebatoski, D.; Jetti, R.; Bandera, Y. P.; Foulger, S. H.; Mefford, O. T. A Versatile Stable Platform for Multifunctional Applications: Synthesis of a NitroDOPA-PEO-alkyne Scaffold for Iron Oxide Nanoparticles J. Mater. Chem. B 2014, 2, 4789-4793 10.1039/C4TB00198B
19. Kim, J. S.; Kim, T. G.; Kong, W. H.; Park, T. G.; Nam, Y. S. Thermally Controlled Wettability of a Nanoporous Membrane Grafted with Catechol-tethered Poly(N-isopropylacrylamide) Chem. Commun. 2012, 48, 9227-9229 10.1039/c2cc32233a
20. Arslan, M.; Gevrek, T. N.; Lyskawa, J.; Szunerits, S.; Boukherroub, R.; Sanyal, R.; Woisel, P.; Sanyal, A. Bioinspired Anchorable Thiol-Reactive Polymers: Synthesis and Applications Toward Surface Functionalization of Magnetic Nanoparticles Macromolecules 2014, 47, 5124-5134 10.1021/ma500693f
21. Sandiford, L.; Phinikaridou, A.; Protti, A.; Meszaros, L. K.; Cui, X.; 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 10.1021/nn3046055
22. He, W.; Zhang, L.; Han, B.; Cheng, L.; Zhou, N.; Liu, Z.; Cheng, Z. Hydrophilic Hybrid Materials with Magnetism & NIR Fluorescence via Surface-initiated RAFT Polymerization J. Mater. Chem. B 2013, 1, 3257-3266 10.1039/c3tb20262c
23. 4 Nanoparticles from Post-atom-transfer-radical-polymerization Modification: Synthesis, Characterization, Cellular Uptake and Imaging J. Mater. Chem. 2012, 22, 6965-6973 10.1039/c2jm15768c
24. Li, H.; Yu, B.; Matsushima, H.; Hoyle, C. E.; Lowe, A. B. The Thiol-Isocyanate Click Reaction: Facile and Quantitative Access to ω-End-Functional Poly(N,N-diethylacrylamide) Synthesized by RAFT Radical Polymerization Macromolecules 2009, 42, 6537-6542 10.1021/ma9010878
25. Scales, C. W.; Convertine, A. J.; McCormick, C. L. Fluorescent Labeling of RAFT-Generated Poly(N-isopropylacrylamide) via a Facile Maleimide-Thiol Coupling Reaction Biomacromolecules 2006, 7, 1389-1392 10.1021/bm060192b
26. 19F Magnetic Resonance Imaging Using Designed Macromolecules J. Am. Chem. Soc. 2010, 132, 5336-5337 10.1021/ja100252y
27. Neubert, B. J.; Snider, B. B. Synthesis of (±)-Phloeodictine A1 Org. Lett. 2003, 5, 765-768 10.1021/ol034042e
28. Shepherd, J. L.; Kell, A.; Chung, E.; Sinclar, C. W.; Workentin, M. S.; Bizzotto, D. Selective Reductive Desorption of a SAM-Coated Gold Electrode Revealed Using Fluorescence Microscopy J. Am. Chem. Soc. 2004, 126, 8329-8335 10.1021/ja0494095
29. Verdoes, M.; Hillaert, U.; Florea, B. I.; Sae-Heng, M.; Risseeuw, M. D. P.; Filippov, D. V.; van der Marel, G. A.; Overkleeft, H. S. Acetylene Functionalized BODIPY Dyes and Their Application in the Synthesis of Activity Based Proteasome Probes Bioorg. Med. Chem. Lett. 2007, 17, 6169-6171 10.1016/j.bmcl.2007.09.025
30. Santi, D. V.; Schneider, E. L.; Reid, R.; Robinson, L.; Ashley, G. W. Predictable and Tunable Half-life Extension of Therapeutic Agents by Controlled Chemical Release from Macromolecular Conjugates Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 6211-6216 10.1073/pnas.1117147109
31. Heredia, K. L.; Grover, G. N.; Tao, L.; Maynard, H. D. Synthesis of Heterotelechelic Polymers for Conjugation of Two Different Proteins Macromolecules 2009, 42, 2360-2367 10.1021/ma8022712
32. McCusker, C. F.; Kocienski, P. J.; Boyle, F. T.; Schatzlein, A. G. Solid-phase Synthesis of c(RGDfK) Derivatives: On-resin Cyclisation and Lysine Functionalisation Bioorg. Med. Chem. Lett. 2002, 12, 547-549 10.1016/S0960-894X(01)00799-5
33. Lai, J. T.; Filla, D.; Shea, R. Functional Polymers from Novel Carboxyl-Terminated Trithiocarbonates as Highly Efficient RAFT Agents Macromolecules 2002, 35, 6754-6756 10.1021/ma020362m
34. Lv, W.; Liu, L.; Luo, Y.; Wang, X.; Liu, Y. Biotinylated Thermoresponsive Core Cross-linked Nanoparticles via RAFT Polymerization and ″Click″ Chemistry J. Colloid Interface Sci. 2011, 356, 16-23 10.1016/j.jcis.2011.01.005
35. Park, J.; An, K.; Hwang, Y.; Park, J.; Noh, H.; Kim, J.; Park, J.; Hwang, N.; Hyeon, T. Ultra-large-scale Syntheses of Monodisperse Nanocrystals Nat. Mater. 2004, 3, 891-895 10.1038/nmat1251
36. Kwon, S. G.; Piao, Y.; Park, J.; Angappane, S.; Jo, Y.; Hwang, N.; Park, J.; Hyeon, T. Kinetics of Monodisperse Iron Oxide Nanocrystal Formation by "Heating-Up" Process J. Am. Chem. Soc. 2007, 129, 12571-12584 10.1021/ja074633q
37. Zobrist, C.; Sobocinski, J.; Lyskawa, J.; Fournier, D.; Miri, V.; Traisnel, M.; Jimenez, M.; Woisel, P. Functionalization of Titanium Surfaces with Polymer Brushes Prepared from a Biomimetic RAFT Agent Macromolecules 2011, 44, 5883-5892 10.1021/ma200853w
38. Watanabe, H.; Fujimoto, A.; Yamamoto, R.; Nishida, J.; Kobayashi, M.; Takahara, A. Scaffold for Growing Dense Polymer Brushes from a Versatile Substrate ACS Appl. Mater. Interfaces 2014, 6, 3648-3653 10.1021/am405965s
39. Nagase, K.; Kobayashi, J.; Kikuchi, A.; Akiyama, Y.; Kanazawa, H.; Annaka, M.; Okano, T. Preparation of Thermoresponsive Anionic Copolymer Brush Surfaces for Separating Basic Biomolecules Biomacromolecules 2010, 11, 215-223 10.1021/bm9010744
40. Yuan, S.; Wan, D.; Liang, B.; Pehkonen, S. O.; Ting, Y. P.; Neoh, K. G.; Kang, E. T. Lysozyme-Coupled Poly(poly(ethylene glycol) methacrylate)-Stainless Steel Hybrids and Their Antifouling and Antibacterial Surfaces Langmuir 2011, 27, 2761-2774 10.1021/la104442f