Mussel-Inspired Multidentate Block Copolymer to Stabilize Ultrasmall Superparamagnetic Fe3O4 for Magnetic Resonance Imaging Contrast Enhancement and Excellent Colloidal Stability

Chemistry of Materials

Volumn 27, Issue 20, 2015, Pages 7100-7109

  Li, Puzhen ^a   Chevallier, Pascale ^b,c   Ramrup, Parsarm ^a   Biswas, Depannita ^a   Vuckovich, Dajana ^a   Fortin, Marc André ^b,c   Oh, Jung Kwon ^a,c  

^a Dept of Electrical and Computer Engineering   (Canada)

^b LAVAL UNIVERSITY   (Canada)

^c UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; BLOCK COPOLYMERS; LIGANDS; MAGNETISM; MOLLUSCS; NANOMAGNETICS; PHENOLS; STABILIZATION; SUPERPARAMAGNETISM; SURFACE CHEMISTRY;

COLLOIDAL STABILITY; CONTROLLED RADICAL POLYMERIZATION; HYDROPHILIC SURFACES; MRI CONTRAST AGENTS; PHYSIOLOGICAL CONDITION; PROTEIN ADSORPTION; SUPERPARAMAGNETICS; ULTRASMALL SUPERPARAMAGNETIC IRON OXIDE NANOPARTICLES;

MAGNETIC RESONANCE IMAGING;

EID: 84945392219     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.5b03028     Document Type: Article

References (51)

1. 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
2. Sun, C.; Lee, J. S. H.; Zhang, M. Magnetic nanoparticles in MR imaging and drug delivery Adv. Drug Delivery Rev. 2008, 60, 1252-1265 10.1016/j.addr.2008.03.018
3. Chen, W.; Cormode, D. P.; Fayad, Z. A.; Mulder, W. J. M. Nanoparticles as magnetic resonance imaging contrast agents for vascular and cardiac diseases Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 2011, 3, 146-161 10.1002/wnan.114
4. Lobatto, M. E.; Fuster, V.; Fayad, Z. A.; Mulder, M. J. M. Perspectives and opportunities for nanomedicine in the management of atherosclerosis Nat. Rev. Drug Discovery 2011, 10, 835-852 10.1038/nrd3578
5. Hu, F.; Zhao, Y. S. Inorganic nanoparticle-based T1 and T1/T2 magnetic resonance contrast probes Nanoscale 2012, 4, 6235-6243 10.1039/c2nr31865b
6. Na, H. B.; Song, I. C.; Hyeon, T. Inorganic Nanoparticles for MRI Contrast Agents Adv. Mater. 2009, 21, 2133-2148 10.1002/adma.200802366
7. Duan, H.; Kuang, M.; Wang, X.; Wang, Y. A.; Mao, H.; Nie, S. Reexamining the Effects of Particle Size and Surface Chemistry on the Magnetic Properties of Iron Oxide Nanocrystals: New Insights into Spin Disorder and Proton Relaxivity J. Phys. Chem. C 2008, 112, 8127-8131 10.1021/jp8029083
8. Hu, F.; Jia, Q.; Li, Y.; Gao, M. Facile synthesis of ultrasmall PEGylated iron oxide nanoparticles for dual-contrast T1- and T2-weighted magnetic resonance imaging Nanotechnology 2011, 22, 245604 10.1088/0957-4484/22/24/245604
9. Kim, B. H.; Lee, N.; Kim, H.; An, K.; Park, Y. I.; Choi, Y.; Shin, K.; Lee, Y.; Kwon, S. G.; Na, H. B.; Park, J.-G.; Ahn, T.-Y.; Kim, Y.-W.; Moon, W. K.; Choi, S. H.; Hyeon, T. Large-Scale Synthesis of Uniform and Extremely Small-Sized Iron Oxide Nanoparticles for High-Resolution T1Magnetic Resonance Imaging Contrast Agents J. Am. Chem. Soc. 2011, 133, 12624-12631 10.1021/ja203340u
10. 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
11. Tromsdorf, U. I.; Bruns, O. T.; Salmen, S. C.; Beisiegel, U.; Weller, H. A Highly Effective, Nontoxic T1MR Contrast Agent Based on Ultrasmall PEGylated Iron Oxide Nanoparticles Nano Lett. 2009, 9, 4434-4440 10.1021/nl902715v
12. Park, J. Y.; Daksha, P.; Lee, G. H.; Woo, S.; Chang, Y. Highly water-dispersible PEG sufrace modified ultra small superparamagnetic iron oxide nanoparticles useful for target-specific biomedical applications Nanotechnology 2008, 19, 365603 10.1088/0957-4484/19/36/365603
13. Amstad, E.; Textor, M.; Reimhult, E. Stabilization and functionalization of iron oxide nanoparticles for biomedical applications Nanoscale 2011, 3, 2819-2843 10.1039/c1nr10173k
14. 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
15. Chung, H.-J.; Lee, H.-S.; Bae, K. H.; Lee, Y.-H.; Park, J.-N.; Cho, S.-W.; Hwang, J.-Y.; Park, H.-W.; Langer, R.; Anderson, D.; Park, T.-G. Facile synthetic route for surface-functionalized magnetic nanoparticles: cell labeling and magnetic resonance imaging studies ACS Nano 2011, 5, 4329-4336 10.1021/nn201198f
16. Zhang, T.; Ge, J.; Hu, Y.; Yin, Y. A General Approach for Transferring Hydrophobic Nanocrystals into Water Nano Lett. 2007, 7, 3203-3207 10.1021/nl071928t
17. Oh, J. K.; Park, J. M. Iron oxide-based superparamagnetic polymeric nanomaterials: Design, preparation, and biomedical application Prog. Polym. Sci. 2011, 36, 168-189 10.1016/j.progpolymsci.2010.08.005
18. Lutz, J.-F.; Stiller, S.; Hoth, A.; Kaufner, L.; Pison, U.; Cartier, R. One-Pot Synthesis of PEGylated Ultrasmall Iron-Oxide Nanoparticles and Their in Vivo Evaluation as Magnetic Resonance Imaging Contrast Agents Biomacromolecules 2006, 7, 3132-3138 10.1021/bm0607527
19. Lu, X.; Jiang, R.; Yang, M.; Fan, Q.; Hu, W.; Zhang, L.; Yang, Z.; Deng, W.; Shen, Q.; Huang, Y.; Liu, X.; Huang, W. Monodispersed grafted conjugated polyelectrolyte-stabilized magnetic nanoparticles as multifunctional platform for cellular imaging and drug delivery J. Mater. Chem. B 2014, 2, 376-386 10.1039/C3TB20955E
20. Basuki, J. S.; Jacquemin, A.; Esser, L.; Li, Y.; Boyer, C.; Davis, T. P. A block copolymer-stabilized co-precipitation approach to magnetic iron oxide nanoparticles for potential use as MRI contrast agents Polym. Chem. 2014, 5, 2611-2620 10.1039/c3py01778h
21. Zhong, Y.; Dai, F.; Deng, H.; Du, M.; Zhang, X.; Liu, Q.; Zhang, X. A rheumatoid arthritis magnetic resonance imaging contrast agent based on folic acid conjugated PEG-b-PAA@SPION J. Mater. Chem. B 2014, 2, 2938-2946 10.1039/C4TB00085D
22. Kumagai, M.; Kano, M. R.; Morishita, Y.; Ota, M.; Imai, Y.; Nishiyama, N.; Sekino, M.; Ueno, S.; Miyazono, K.; Kataoka, K. Enhanced magnetic resonance imaging of experimental pancreatic tumor in vivo by block copolymer-coated magnetite nanoparticles with TGF-b inhibitor J. Controlled Release 2009, 140, 306-311 10.1016/j.jconrel.2009.06.002
23. Chan, N.; Laprise-Pelletier, M.; Chevallier, P.; Bianchi, A.; Fortin, M.-A.; 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
24. Chan, N.; Li, P.; Oh, J. K. Chain Length Effect of the Multidentate Block Copolymer Strategy to Stabilize Ultrasmall Fe3O4 Nanoparticles ChemPlusChem 2014, 79, 1342-1351 10.1002/cplu.201402112
25. Torrisi, V.; Graillot, A.; Vitorazi, L.; Crouzet, Q.; Marletta, G.; Loubat, C.; Berret, J. F. Preventing Corona Effects: Multiphosphonic Acid Poly(ethylene glycol) Copolymers for Stable Stealth Iron Oxide Nanoparticles Biomacromolecules 2014, 15, 3171-3179 10.1021/bm500832q
26. Moulay, S. Dopa/Catechol-Tethered Polymers: Bioadhesives and Biomimetic Adhesive Materials Polym. Rev. 2014, 54, 436-513 10.1080/15583724.2014.881373
27. Yuen, A. K. L.; Hutton, G. A.; Masters, A. F.; Maschmeyer, T. The interplay of catechol ligands with nanoparticulate iron oxides Dalton Trans. 2012, 41, 2545-2559 10.1039/c2dt11864e
28. Xiao, L.-S.; Li, J.-T.; Brougham, D. F.; Fox, E. K.; Feliu, N.; Bushmelev, A.; Schmidt, A.; Mertens, N.; Kiessling, F.; Valldor, M.; Fadeel, B.; Mathur, S. Water-Soluble Superparamagnetic Magnetite Nanoparticles with Biocompatible Coating for Enhanced Magnetic Resonance Imaging ACS Nano 2011, 5, 6315-6324 10.1021/nn201348s
29. 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
30. 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
31. Gillich, T.; Acikgoez, C.; Isa, L.; Schluter, A. D.; Spencer, N. D.; Textor, M. PEG-Stabilized Core-Shell Nanoparticles: Impact of Linear versus Dendritic Polymer Shell Architecture on Colloidal Properties and the Reversibility of Temperature-Induced Aggregation ACS Nano 2013, 7, 316-329 10.1021/nn304045q
32. 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
33. Amstad, E.; Gehring, A. U.; Fischer, H.; Nagaiyanallur, V. V.; Hahner, G.; Textor, M.; Reimhult, E. Influence of electronegative substituents on the binding affinity of catechol-derived anchors to Fe3O4 nanoparticles J. Phys. Chem. C 2011, 115, 683-691 10.1021/jp1109306
34. Martin, M.; Salazar, P.; Villalonga, R.; Campuzano, S.; Pingarron, J. M.; Gonzalez-Mora, J. L. Preparation of core-shell Fe3O4@poly(dopamine) magnetic nanoparticles for biosensor construction J. Mater. Chem. B 2014, 2, 739-746 10.1039/C3TB21171A
35. 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
36. Shukoor, M. I.; Natalio, F.; Therese, H. A.; Tahir, M. N.; Ksenofontov, V.; Panthoefer, M.; Eberhardt, M.; Theato, P.; Schroeder, H. C.; Mueller, W. E. G.; Tremel, W. Fabrication of a Silica Coating on Magnetic γ-Fe2O3 Nanoparticles by an Immobilized Enzyme Chem. Mater. 2008, 20, 3567-3573 10.1021/cm7029954
37. Lee, Y.; Lee, H.; Kim, Y. B.; Kim, J.; Hyeon, T.; Park, H.; Messersmith, P. B.; Park, T. G. Bioinspired surface immobilization of hyaluronic acid on monodisperse magnetite nanocrystals for targeted cancer imaging Adv. Mater. 2008, 20, 4154-4157 10.1002/adma.200800756
38. 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 10.1002/anie.201101521
39. Brannon-Peppas, L. Poly(ethylene glycol): Chemistry and Biological Applications; Harris, J. M.; Zalipsky, S., Eds.; ACS Symposium Series, American Chemical Society: Washington DC, 1997; Vol. 680.
40. Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U. S. Poly(ethylene glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives Angew. Chem., Int. Ed. 2010, 49, 6288-6308 10.1002/anie.200902672
41. Xie, J.; Xu, C.; Kohler, N.; Hou, Y.; Sun, S. Controlled PEGylation of monodisperse Fe3O4 nanoparticles for reduced non-specific uptake by macrophage cells Adv. Mater. 2007, 19, 3163-3166 10.1002/adma.200701975
42. Britovsek, G. J. P.; England, J.; White, A. J. P. Non-heme Iron(II) Complexes Containing Tripodal Tetradentate Nitrogen Ligands and Their Application in Alkane Oxidation Catalysis Inorg. Chem. 2005, 44, 8125-8134 10.1021/ic0509229
43. An, S. Y.; Hwang, J. W.; Kim, K. N.; Jung, H. W.; Noh, S. M.; Oh, J. K. Multifunctional linear methacrylate copolymer polyenes having pendant vinyl groups: Synthesis and photoinduced thiol-ene crosslinking polyaddition J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 572-581 10.1002/pola.27035
44. Kamigaito, M.; Ando, T.; Sawamoto, M. Metal-Catalyzed Living Radical Polymerization Chem. Rev. 2001, 101, 3689-3745 10.1021/cr9901182
45. Matyjaszewski, K.; Xia, J. Atom Transfer Radical Polymerization Chem. Rev. 2001, 101, 2921-2990 10.1021/cr940534g
46. Smolensky, E. D.; Park, H.-Y. E.; Berquo, T. S.; Pierre, V. C. Surface functionalization of magnetic iron oxide nanoparticles for MRI applications-effect of anchoring group and ligand exchange protocol Contrast Media Mol. Imaging 2011, 6, 189-199 10.1002/cmmi.417
47. Patil, S.; Sandberg, A.; Heckert, E.; Self, W.; Seal, S. Protein adsorption and cellular uptake of cerium oxide nanoparticles as a function of zeta potential Biomaterials 2007, 28, 4600-4607 10.1016/j.biomaterials.2007.07.029
48. Wen, Y.; Oh, J. K. Intracellular delivery cellulose-based bionanogels with dual temperature/pH-response for cancer therapy Colloids Surf., B 2015, 133, 246-253 10.1016/j.colsurfb.2015.06.017
49. Simon, G. H.; von Vopelius-Feldt, J.; Fu, Y.; Schlegel, J.; Pinotek, G.; Wendland Michael, F.; Chen, M.-H.; Daldrup-Link Heike, E. Ultrasmall supraparamagnetic iron oxide-enhanced magnetic resonance imaging of antigen-induced arthritis: a comparative study between SHU 555 C, ferumoxtran-10, and ferumoxytol Invest. Radiol. 2006, 41, 45-51 10.1097/01.rli.0000191367.61306.83
50. Rohrer, M.; Bauer, H.; Mintorovitch, J.; Requardt, M.; Weinmann, H.-J. Comparison of magnetic properties of MRI contrast media solutions at different magnetic field strengths Invest. Radiol. 2005, 40, 715-24 10.1097/01.rli.0000184756.66360.d3
51. Ai, H.; Flask, C.; Weinberg, B.; Shuai, X.; Pagel, M. D.; Farrell, D.; Duerk, J.; Gao, J. Magnetite-loaded polymeric micelles as ultrasensitive magnetic-resonance probes Adv. Mater. 2005, 17, 1949-1952 10.1002/adma.200401904