journal article·2012-09Open access

Improved functionalization of oleic acid-coated iron oxide nanoparticles for biomedical applications

Maarten Bloemen, Ward Brullot, Tai Thien Luong, Nick Geukens, Ann Gils, Thierry Verbiest

Journal of Nanoparticle Research· Volume 14· Issue 9

Abstract

Superparamagnetic iron oxide nanoparticles can provide multiple benefits for biomedical applications in aqueous environments such as magnetic separation or magnetic resonance imaging. To increase the colloidal stability and allow subsequent reactions, the introduction of hydrophilic functional groups onto the particles' surface is essential. During this process, the original coating is exchanged by preferably covalently bonded ligands such as trialkoxysilanes. The duration of the silane exchange reaction, which commonly takes more than 24 h, is an important drawback for this approach. In this paper, we present a novel method, which introduces ultrasonication as an energy source to dramatically accelerate this process, resulting in high-quality water-dispersible nanoparticles around 10 nm in size. To prove the generic character, different functional groups were introduced on the surface including polyethylene glycol chains, carboxylic acid, amine, and thiol groups. Their colloidal stability in various aqueous buffer solutions as well as human plasma and serum was investigated to allow implementation in biomedical and sensing applications. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s11051-012-1100-5) contains supplementary material, which is available to authorized users.
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Research context

OpenAlex topics: Nanoparticle-Based Drug Delivery · Iron oxide chemistry and applications · Characterization and Applications of Magnetic Nanoparticles

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References (36)

Show source-provided references
1. Barreto JA, Matterna M, Graham B, Stephan H, Spiccia L (2011) Synthesis, colloidal stability and 64Cu labeling of iron oxide nanoparticles bearing different macrocyclic ligands. N J Chem 35:2705–2712. doi: 10.1039/c1nj20558g10.1039/c1nj20558g ↗
2. Bhattacharya D, Sahu SK, Banerjee I et al (2011) Synthesis, characterization, and in vitro biological evaluation of highly stable diversely functionalized superparamagnetic iron oxide nanoparticles. J Nanoparticle Res 13:4173–4188. doi: 10.1007/s11051-011-0362-710.1007/s11051-011-0362-7 ↗
3. Bronstein LM, Huang X, Retrum J, Schmucker A, Pink M, Stein BD, Dragnea B (2007) Influence of iron oleate complex structure on iron oxide nanoparticle formation. Chem Mater 19:3624–3632. doi: 10.1021/cm062948j10.1021/cm062948j ↗
4. Brullot W, Valev VK, Verbiest T (2011) Magnetic-plasmonic nanoparticles for the life sciences: calculated optical properties of hybrid structures. Nanomedicine 8(5):559–568. doi: 10.1016/j.nano.2011.09.00410.1016/j.nano.2011.09.004 ↗
5. Brullot W, Reddy NK, Wouters J, Valev VK, Goderis B, Vermant J, Verbiest T (2012) Versatile ferrofluids based on polyethylene glycol coated iron oxide nanoparticles. J Magn Magn Mater 11:1919–1925. doi: 10.1016/j.jmmm.2012.01.03210.1016/j.jmmm.2012.01.032 ↗
6. Can K, Ozmen M, Ersoz M (2009) Immobilization of albumin on aminosilane modified superparamagnetic magnetite nanoparticles and its characterization. Colloids Surf B, Biointerfaces 71:154–159. doi: 10.1016/j.colsurfb.2009.01.02110.1016/j.colsurfb.2009.01.021 ↗
7. Chen ZP, Xu RZ, Zhang Y, Gu N (2008a) Effects of proteins from culture medium on surface property of silanes-functionalized magnetic nanoparticles. Nanoscale Res Lett 4:204–209. doi: 10.1007/s11671-008-9226-110.1007/s11671-008-9226-1 ↗
8. Chen ZP, Zhang Y, Xu K, Xu RZ, Liu JW, Gu N (2008b) Stability of hydrophilic magnetic nanoparticles under biologically relevant conditions. J Nanoscience Nanotechnol 8:6260–6265. doi: 10.1166/jnn.2008.34310.1166/jnn.2008.343 ↗
9. Cornell RM, Schwertmann U (2003) The iron oxides. Wiley, Weinheim10.1002/3527602097 ↗
10. De Palma R, Peeters S, Van Bael MJ, Van den Rul H, Bonroy K, Laureyn W, Mullens J, Borghs G, Maes G (2007) Silane ligand exchange to make hydrophobic superparamagnetic nanoparticles water-dispersible. Chem Mater 19:1821–183110.1021/cm0628000 ↗
11. Fadeev AY, McCarthy TJ (2000) Self-assembly is not the only reaction possible between alkyltrichlorosilanes and surfaces: monomolecular and oligomeric covalently attached layers of dichloro- and trichloroalkylsilanes on silicon. Langmuir 16:7268–727410.1021/la000471z ↗
12. Fauconnier N, Pons J, Roger J, Bee A (1997) Thiolation of maghemite nanoparticles by dimercaptosuccinic acid. J Colloid Interface Sci 194:427–43310.1006/jcis.1997.5125 ↗
13. Harder P, Grunze M, Dahint R, Whitesides G, Laibinis P (1998) Molecular conformation in oligo (ethylene glycol)-terminated self-assembled monolayers on gold and silver surfaces determines their ability to resist protein adsorption. J Phys Chem B 102:426–43610.1021/jp972635z ↗
14. Janib SM, Moses AS, MacKay JA (2010) Imaging and drug delivery using theranostic nanoparticles. Adv Drug Del Rev 62:1052–1063. doi: 10.1016/j.addr.2010.08.00410.1016/j.addr.2010.08.004 ↗
15. Kohler N, Fryxell GE, Zhang M (2004) A bifunctional poly (ethylene glycol) silane immobilized on metallic oxide-based nanoparticles for conjugation with cell targeting agents. J Am Chem Soc 126:7206–7211. doi: 10.1021/ja049195r10.1021/ja049195r ↗
16. Kreuzer HJ, Wang RLC, Grunze M (2003) Hydroxide ion adsorption on self-assembled monolayers. J Am Chem Soc 125:8384–8389. doi: 10.1021/ja035083910.1021/ja0350839 ↗
17. Larsen EKU, Nielsen T, Wittenborn T, Birkedal H, Vorup-Jensen T et al (2009) Size-dependent accumulation of PEGylated silane-coated magnetic iron oxide nanoparticles in murine tumors. ACS Nano 3:1947–1951. doi: 10.1021/nn900330m10.1021/nn900330m ↗
18. Laurent S, Forge D, Port M, Roch A, Robic C, Vander Elst L, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev 108:2064–2110. doi: 10.1021/cr900197g10.1021/cr068445e ↗
19. Ma M, Zhang Y, Yu W, Shen H, Zhang H, Gu N (2003) Preparation and characterization of magnetite nanoparticles coated by amino silane. Colloids Surf A: Physicochem Eng Asp 212:219–226. doi: 10.1016/S0927-7757(02)00305-910.1016/S0927-7757(02)00305-9 ↗
20. Mahmoudi M, Laurent S, Shokrgozar MA, Hosseinkhani M (2011) Toxicity evaluations of superparamagnetic iron oxide nanoparticles: cell “vision” versus physicochemical properties of nanoparticles. ACS Nano 5:7263–7276. doi: 10.1021/nn202108810.1021/nn2021088 ↗
21. Mason T, Lorimer J (2002) Applied sonochemistry: uses of power ultrasound in chemistry and processing. Wiley, Weinheim10.1002/352760054X ↗
22. Morel A-L, Nikitenko SI, Gionnet K, Wattiaux A et al (2008) Sonochemical approach to the synthesis of Fe(3)O(4)@SiO(2) core-shell nanoparticles with tunable properties. ACS Nano 2:847–856. doi: 10.1021/nn800091q10.1021/nn800091q ↗
23. Park J, An K, Hwang Y, Park JG, Noh HJ, Kim JY, Park JH, Hwang NM, Hyeon T (2004) Ultra-large-scale syntheses of monodisperse nanocrystals. Nat Mater 3:891–895. doi: 10.1038/nmat125110.1038/nmat1251 ↗
24. Park JW, Bae KH, Kim C, Park TG (2011) Clustered magnetite nanocrystals cross-linked with PEI for efficient siRNA delivery. Biomacromolecules 12:457–465. doi: 10.1021/bm101244j10.1021/bm101244j ↗
25. Prasad NK, Rathinasamy K, Panda D, Bahadur D (2007) Mechanism of cell death induced by magnetic hyperthermia with nanoparticles of γ-MnxFe2–xO3 synthesized by a single step process. J Mater Chem 17:5042–5051. doi: 10.1039/b708156a10.1039/b708156a ↗
26. Schweiss R, Welzel PB, Werner C, Knoll W (2001) Dissociation of surface functional groups and preferential adsorption of ions on self-assembled monolayers assessed by streaming potential and streaming current measurements. Langmuir 17:4304–431110.1021/la001741g ↗
27. Soderholm K-JM, Shang S-W (1993) Molecular orientation of silane at the surface of colloidal silica. J Dental Res 72:1050–1054. doi: 10.1177/0022034593072006100110.1177/00220345930720061001 ↗
28. Speliotis D (1999) Magnetic recording beyond the first 100 years. J Magn Magn Mater 193:29–35. doi: 10.1016/S0304-8853(98)00399-010.1016/S0304-8853(98)00399-0 ↗
29. Sun S, Zeng H, Robinson DB, Raoux S, Rice PM, Wang SX, Li G (2004) Monodisperse MFe2O4 (M=Fe, Co., Mn) nanoparticles. J Am Chem Soc 126:273–279. doi: 10.1021/ja038085210.1021/ja0380852 ↗
30. Sun J, Zhou S, Hou P, Yang Y (2006) Synthesis and characterization of biocompatible Fe3O4 nanoparticles. J Biomed Mater Res, pp 333–341. doi: 10.1002/jbm.a
31. Tartaj P, Morales MDP, Veintemillas-Verdaguer S, Gonzalez-Carreno T, Serna CJ (2003) The preparation of magnetic nanoparticles for applications in biomedicine. J Phys D Appl Phys 36:182–197. doi: 10.1088/0022-3727/36/13/20210.1088/0022-3727/36/13/202 ↗
32. Valiokas R, Svedhem S, Svensson S (1999) Self-assembled monolayers of oligo (ethylene glycol)-terminated and amide group containing alkanethiolates on gold. Langmuir 15:3390–339410.1021/la981647o ↗
33. Wang Y, Wong JF, Teng X, Lin XZ, Yang H (2003) “Pulling” nanoparticles into water: phase transfer of oleic acid stabilized monodisperse nanoparticles into aqueous solutions of α-cyclodextrin. Nano Lett 3:1555–1559. doi: 10.1021/nl034731j10.1021/nl034731j ↗
34. Xu R (2001) Particle characterization: light scattering methods. Kluwer Academic Publishers, Greenbelt, p 403
35. Zhang Y, Kohler N, Zhang M (2002) Surface modification of superparamagnetic magnetite nanoparticles and their intracellular uptake. Biomaterials 23:1553–156110.1016/S0142-9612(01)00267-8 ↗
36. Zhang L, He R, Gu H (2006) Oleic acid coating on the monodisperse magnetite nanoparticles. Appl Surf Sci 253:2611–2617. doi: 10.1016/j.apsusc.2006.05.02310.1016/j.apsusc.2006.05.023 ↗