Abstract
Fe3O4 magnetic nanoparticles (MNPs) were obtained using the gas condensation method. These MNPs were modified with 3-aminopropylsilane (APS) through covalent bonding. The methods of qualitative and quantitative analysis of the modified MNPs were developed using UV and IR spectroscopy and inductively coupled plasma emission spectrometry (ICP-ES). It was established that the maximum loading level of APS on the surface of Fe3O4 MNPs was 0.91 mmol/g MNP. The study of the activity of the surface amino groups of the nanocomposites was carried out by the example of their modification with (S)-naproxen. The optimum conditions for coupling reaction were found. It was shown that the reaction proceeded most efficiently when using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) as coupling agent in the presence of 1-hydroxy-1H-benzotriazole (HOBt). The maximum immobilization level of (S)-naproxen on the Fe3O4 MNP surface was 0.55 mmol/g MNP. Thus, the high reactivity of amino groups of the obtained nano-composites was shown, making it possible to further modify them.
Similar content being viewed by others
References
C. Sanchez, P. Belleville, M. Popall, and L. Nicole, “Applications of Advanced Hybrid Organic-Inorganic Nanomaterials: From Laboratory to Market,” Chem. Soc. Rev. 40, 696–753 (2011).
S. Chandra, K. C. Barick, and D. Bahadu, “Oxide and Hybrid Nanostructures for Therapeutic Applications,” Adv. Drug Deliv. Rev. 63, 1267–1281 (2011).
O. Veiseh, J. W. Gunn, and M. Zhang, “Design and Fabrication of Magnetic Nanoparticles for Targeted Drug Delivery and Imaging,” Adv. Drug Deliv. Rev. 62, 284–304 (2010).
J. Xie, G. Liu, H. S. Eden, H. Ai, and X. Chen, “Surface-Engineered Magnetic Nanoparticle Platforms for Cancer Imaging and Therapy,” Acc. Chem. Res. 44, 883–892 (2011).
A. H. Faraji and P. Wipf, “Nanoparticles in Cellular Drug Delivery,” Bioorg. Med. Chem. 17, 2950–2962 (2009).
M. A. M. Gijs, F. Lacharme, and U. Lehmann, “Microfluidic Applications of Magnetic Particles for Biological Analysis and Catalysis,” Chem. Rev. 110, 1518–1563 (2010).
I. Safarik and M. Safarikova, “Magnetic Nano- and Microparticles in Biotechnology,” Chem. Pap. 63, 497–505 (2009).
J. Gao, H. Gu, and B. Xu, “Multifunctional Magnetic Nanoparticles: Design, Synthesis, and Biomedical Applications,” Acc. Chem. Res. 42, 1097–1107 (2009).
A. Schatz, R. N. Grass, Q. Kainz, W. J. Stark, and O. Reiser, “Cu(II)-Azabis(Oxazoline) Complexes Immobilized on Magnetic Co/C Nanoparticles: Kinetic Resolution of 1,2-Diphenylethane-1,2-Diol under Batch and Continuous-Flow Conditions,” Chem. Mater. 22, 305–310 (2010).
X. Zhang, P. Li, Y. Ji, L. Zhang, and L. Wang, “An Efficient and Recyclable Magnetic-Nanoparticle-Supported Palladium Catalyst for the Suzuki Coupling Reactions of Organoboronic Acids with Alkynyl Bromides,” Synthesis 18, 2975–2983 (2011).
M. Z. Kassaee, H. Masrouri, and F. Movahedi, “Sulfamic Acid-Functionalized Magnetic Fe3O4 Nanoparticles as an Efficient and Reusable Catalyst for One-Pot Synthesis of α-Amino Nitriles in Water,” Appl. Catal. A: Gen. 395, 28–33 (2011).
D. K. Yi, S. S. Lee, and J. Y. Ying, “Synthesis and Applications of Magnetic Nanocomposite Catalysts,” Chem. Mater. 18, 2459–2461 (2006).
Y. Zheng, C. Duanmu, and Y. Gao, “A Magnetic Biomimetic Nanocatalyst for Cleaving Phosphoester and Carboxylic Ester Bonds under Mild Conditions,” Org. Lett. 8, 3215–3217 (2006).
B. Srinivasan and X. Huang, “Functionalization of Magnetic Nanoparticles with Organic Molecules: Loading Level Determination and Evaluation of Linker Length Effect on Immobilization,” Chirality 20, 265–277 (2008).
I. J. Bruce and T. Sen, “Surface Modification of Magnetic Nanoparticles with Alkoxysilanes and Their Application in Magnetic Bioseparations,” Langmuir 21, 7029–7035 (2005).
R. de Palma, S. Peeters, M. J. van Bael, H. vah den Rul, K. Bonroy, W. Laureyn, J. Mullens, G. Borghs, and G. Maes, “Silane Ligand Exchange to Make Hydrophobic Superparamagnetic Nanoparticles Water-Dispersible,” Chem. Mater. 19, 1821–1831 (2007).
X. Liu, Z. Ma, J. Xing, and H. Liu, “Preparation and Characterization of Amino-Silane Modified Superparamagnetic Silica Nanospheres,” J. Magn. Magn. Mater. 270, 1–6 (2004).
T. Tanaka, R. Sakai, R. Kobayashi, K. Hatakeyama, and T. Matsunaga, “Contributions of Phosphate to DNA Adsorption Desorption Behaviors on Aminosilane-Modified Magnetic Nanoparticles,” Langmuir 25, 2956–2961 (2009).
K. Kang, J. Choi, J. H. Nam, S. C. Lee, K. J. Kim, S.-W. Lee, and J. H. Chang, “Preparation and Characterization of Chemically Functionalized Silica-Coated Magnetic Nanoparticles as a DNa Separator,” J. Phys. Chem. B 113, 536–543 (2009).
S. Gui, X. Shen, and B. Lin, “Surface Organic Modification of Fe3O4 Nanoparticles by Silane-Coupling Agents,” Rare Metals 25, 426–430 (2006).
T. Osaka, T. Matsunaga, T. Nakanishi, A. Arakaki, D. Niwa, and H. Iida, “Synthesis of Magnetic Nanoparticles and Their Application to Bioassays,” Anal. Bioanal. Chem. 384, 593–600 (2006).
F. Sulek, Z. Knez, and M. Habulin, “Immobilization of Cholesterol Oxidase to Finely Dispersed Silica-Coated Maghemite Nanoparticles Based Magnetic Fluid,” Appl. Surf. Sci. 256, 4596–4600 (2010).
J. O. Park, K. Y. Rhee, and S. J. Park, “Silane Treatment of Fe3O4 and Its Effect on the Magnetic and Wear Properties of Fe3O4/Epoxy Nanocomposites,” Appl. Surf. Sci. 256, 6945–6950 (2010).
H. Cao, J. He, L. Deng, and X. Gao, Fabrication of Cyclodextrin-Functionalized Superparamagnetic Fe3O4/Amino-Silane Core-Shell Nanoparticles via Layer-by-Layer Method,” Appl. Surf. Sci. 255, 7974–7980 (2009).
H. Iida, T. Nakanishi, and T. Osaka, “Surface Modification of γ-Fe2O3 Nanoparticles with Aminopropylsilyl Groups and Interparticle Linkage with α,ω-Dicarboxylic Acids,” Electrochim. Acta 51, 855–859 (2005).
N. Kohler, G. E. Fryxell, and M. Zhang, “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 (2004).
B. N. Khlebtsov, E. V. Panfilova, V. A. Khanadeev, A. V. Markin, G. S. Terentyuk, V. D. Rumyantseva, A. V. Ivanov, I. P. Shilov, and N. G. Khlebtsov, “Composite Multifunctional Nanoparticles Based on Silica-Coated Gold-Silver Nanocages Functionalized by Yb-Hematoporphyrin,” Nanotechnol. Russ. 6, 496–503 (2011).
S. S. Adams and R. Cobb, “Nonsteroidal Anti-Inflammatory Drugs,” Prog. Med. Chem. 5, 59–138 (1967).
V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Korolyova, M. I. Kodess, O. N. Chupakhin, M. H. Kim, H. S. Lee, Y. J. Park, and K.-C. Kim, “Kinetic Resolution of (±)-2,3-Dihydro-3-Methyl-4H-1,4-Benzoxazines with (S)-Naproxen,” Tetrahedron: Asymmetry 10, 2691–2702 (1999).
E. N. Chulakov, D. A. Gruzdev, G. L. Levit, L. Sh. Sadretdinova, V. P. Krasnov, and V. N. Charushin, “2-Arylpropionyl Chlorides in Kinetic Resolution of Racemic 3-Methyl-2,3-Dihydro-4H-[1,4]Benzoxazines,” Russ. Chem. Bull. 60, 948–954 (2011).
C. Wolf and W. H. Pirkle, “Conformational Effects on the Enantioselective Recognition of 4-(3,5-Dinitrobenzoamido)1,2,3,4-Tetrahydrophenanthrene Derivatives by a Naproxen-Derived Chiral Stationary Phase,” J. Chromatogr. A 58, 3597–3603 (2002).
A. Andreou, N. Al Shaye, H. Brown, and J. Eames, “Resolution of (4RS,5RS)-4,5-Diphenylimidazolidine-2-Thione Using Pentafluorophenyl Active Esters,” Tetrahedron Lett. 51, 6935–6938 (2010).
V. P. Krasnov, G. L. Levit, V. N. Charushin, A. N. Grisha- kov, M. I. Kodess, V. N. Kalinin, V. A. Ol’shevskaya, and O. N. Chupakhin, “Enantiomers of 3-Amino-1-Methyl-1,2-Dicarba-Closo-Dodecaborane,” Tetrahedron: Asymmetry 13, 1833–1835 (2002).
G. L. Levit, V. P. Krasnov, A. M. Demin, M. I. Kodess, L. Sh. Sadretdinova, T. V. Matveeva, O. N. Chupakhin, V. N. Charushin, V. A. Ol’shevskaya, and V. N. Kalinin, “Kinetic Resolution of 1-Methyl- and 1-Phenyl-3-Amino-1,2-Dicarba-Closo-Dodecaboranes via Acylation with Chiral Acyl Chlorides,” Mendeleev Commun. 14, 293–295 (2004).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.M. Demin, M.A. Uimin, N.N. Shchegoleva, A.E. Yermakov, V.P. Krasnov, 2012, published in Rossiiskie Nanotekhnologii, 2012, Vol. 7, Nos. 3–4.
Rights and permissions
About this article
Cite this article
Demin, A.M., Uimin, M.A., Shchegoleva, N.N. et al. Surface modification of Fe3O4 magnetic nanoparticles with (S)-naproxen. Nanotechnol Russia 7, 132–139 (2012). https://doi.org/10.1134/S199507801202005X
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S199507801202005X