Surface modification of magnetite nanoparticle with azobenzene-containing water dispersible polymer
Source abstract
Abstract
We here report the synthesis of magnetite nanoparticle (MNP) grafted with poly (ethylene glycol) methyl ether methacrylate (PEGMA)-azobenzene acrylate (ABA) statistical copolymer via atom transfer radical polymerization (ATRP) for drug entrapment and photocontrolled release. MNP was synthesized via thermal decomposition of iron (III) acetylacetonate in benzyl alcohol and surface functionalized to obtain ATRP initiating sites. Molar compositions of the copolymer on MNP surface were systematically varied (100:0, 90:10, 70:30, and 50:50 of PEGMA:ABA, respectively) to obtain water dispersible particles with various amounts of azobenzene. The presence of polymeric shell on MNP core was evidenced by transmission electron microscopy (TEM). Drug loading and entrapment efficiencies as well as drug release behavior of the copolymer–MNP complexes were investigated. It was found that when percent of ABA in the copolymers was increased, entrapment and loading efficiencies of prednisolone model drug were enhanced. Releasing rate and percent of the released prednisolone of the complex exposed in UV light were slightly enhanced as compared to the system without UV irradiation. This copolymer–MNP complex with photocontrollable drug release and magnetic field-directed properties is warranted for further studies for potential uses as a novel drug delivery vehicle.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanoparticle-Based Drug Delivery · Iron oxide chemistry and applications · Surfactants and Colloidal Systems
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (42)
Show source-provided references
1. Anders S, Sun S, Murray CB, Rettner CT, Best ME, Thomson T, Albrecht M, Thiele J-U, Fullerton EE, Terris BD (2002) Lithography and self-assembly for nanometer scale magnetism. Microelectron Eng 61–62:569–57510.1016/S0167-9317(02)00522-1 ↗
2. Archut A, Azzellini GC, Balzani V, Cola LD, Vgtle F (1998) Toward photoswitchable dendritic hosts Interaction between azobenzene-functionalized dendrimers and erosin. J Am Chem Soc 120:12187–1219110.1021/ja9822409 ↗
3. Aruna P, Rao BS (2009) Ionomeric poly(urethane semicarbazides) with azobenzene groups in the main chain-studies on photoswitching behavior and mechanical properties. React Funct Polym 69:20–2610.1016/j.reactfunctpolym.2008.10.005 ↗
4. Bucio E, Skewes P, Burillo G (2005) Synthesis and characterization of azo acrylates grafted onto polyethylene terephthalate by gamma irradiation. Nucl Instrum Methods Phys Res 236:301–30610.1016/j.nimb.2005.03.262 ↗
5. Dokic J, Gothe M, Wirth J, Peters MV, Schwarz J, Hecht S, Saalfrank P (2009) Quantum chemical investigation of thermal cis-to-trans isomerization of azobenzene derivatives: substituent effects, solvent effects, and comparison to experimental data. J Phys Chem A 113:6763–677310.1021/jp9021344 ↗
6. Fan QL, Neoh KG, Kang ET, Shuter B, Wang SC (2007) Solvent-free atom transfer radical polymerization for the preparation of poly (poly(ethyleneglycol) monomethacrylate)-grafted Fe3O4 nanoparticles: synthesis, characterization and cellular uptake. Biomaterials 28:5426–543610.1016/j.biomaterials.2007.08.039 ↗
7. Fischer H (1999) The persistent radical effect in controlled radical polymerizations. J Polym Sci A 37:1885–190110.1002/(SICI)1099-0518(19990701)37:13<1885::AID-POLA1>3.0.CO;2-1 ↗
8. Fischer H (2001) The persistent radical effect: a principle for selective radical reactions and living radical polymerizations. Chem Rev 101:3581–361010.1021/cr990124y ↗
9. Fujiwara M, Akiyama M, Hata M, Shiokawa K, Nomura R (2008) Photoinduced acceleration of the effluent rate of developing solvents in azobenzene-tethered silica gel. ACS Nano 2:1671–168110.1021/nn800290p ↗
10. Hermann High LR, Holder SJ, Penfold HV (2007) Synthesis of star polymers of styrene and alkyl (Meth)acrylates from a porphyrin initiator core via ATRP. Macromolecules 40:7157–716510.1021/ma062870s ↗
11. Hu F, Neoh KG, Cen L, Kang ET (2006) Cellular response to magnetic nanoparticles “PEGylated” via surface-initiated atom transfer radical polymerization. Biomacromolecules 7:809–81610.1021/bm050870e ↗
12. Kalyanasundaram K, Thomas JK (1977) Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc 99:2039–204410.1021/ja00449a004 ↗
13. Kim SY, Lee YM, Kang JS (2005) Indomethacin-loaded methoxy poly(ethylene glycol)/poly(d, l-lactide) amphiphilic diblock copolymericnanospheres: pharmacokinetic and toxicity studies in rodents. J Biomed Mater Res A 74A:581–59010.1002/jbm.a.30342 ↗
14. Laurent S, Forge D, Port M, Roch A, Robic C, Elst LV, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev 108:2064–211010.1021/cr068445e ↗
15. Lee JH, Carraway ER, Schlautman MA, Yim S, Herbert BE (2004) Characterizing pyrene-Ag+ exciplex formation in aqueous and ethanolic solutions. J Photochem Photobiol A 167:141–14810.1016/j.jphotochem.2004.04.012 ↗
16. Li Y, Deng Y, Tong X, Wang X (2006) Formation of photoresponsive uniform colloidal spheres from an amphiphilic azobenzene-containing random copolymer. Macromolecules 39:1108–111510.1021/ma052272y ↗
17. Liu KW, Bian S, Li L, Samuelson L, Kumar J, Tripathy S (2000) Enzymatic synthesis of photoactive poly(4-phenylazophenol). Chem Mater 12:1577–158410.1021/cm000072p ↗
18. Liu G, Yan X, Lu Z, Curda SA, Lal J (2005) One-Pot synthesis of block copolymer coated cobalt nanocrystals. Chem Mater 17:4985–499110.1021/cm051050b ↗
19. Maria PD, Fontana A, Gasbarri C, Siani G, Zaniratob P (2009) Kinetics of the Z–E isomerization of monosubstituted azobenzenes in polar organic and aqueous micellar solvents. Arkivoc 8:16–29
20. Marutani E, Yamamoto S, Ninjbadgar T, Tsujii Y, Fukuda T, Takano M (2004) Surface-initiated atom transfer radical polymerization of methyl methacrylate on magnetite nanoparticles. Polymer 45:2231–223510.1016/j.polymer.2004.02.005 ↗
21. Moineau G, Granel C, Dubois Ph, Jerome R, Teyssie P (1998) Controlled radical polymerization of methyl methacrylate initiated by an alkyl halide in the presence of the wilkinson catalyst. Macromolecules 31:542–54410.1021/ma971123f ↗
22. Monteiro MJ, Adamy MM, Leeuwen BJ, Herk AM, Destarac M (2005) “Living” radical ab initio emulsion polymerization of styrene using a fluorinated xanthate agent. Macromolecules 38:1538–154110.1021/ma0478557 ↗
23. Neugebauer D (2007) Graft copolymers with hydrophilic and hydrophobic polyether side chains. Polymer 48:4966–497310.1016/j.polymer.2007.06.037 ↗
24. Nishimura N, Kosako S, Sueishi Y (1984) The thermal isomerization of azobenzenes. III. Substituent, solvent, and pressure effect on the thermal isomerization of push-pull azobenzenes. Bull Chem Soc Jpn 57:1617–162510.1246/bcsj.57.1617 ↗
25. Park EK, Lee SB, Lee YM (2001) Preparation and characterization of methoxy poly(ethylene glycol)/poly(e-caprolactone) amphiphilic block copolymeric nanospheres for tumor-specific folate-mediated targeting of anticancer drugs. Biomaterials 26:1053–106110.1016/j.biomaterials.2004.04.008 ↗
26. Pei W, Kumada H, Natusma T, Saito H, Ishio S (2007) Study on magnetite nanoparticles synthesized by chemical method. J Mag Magn Mater 310:2375–237710.1016/j.jmmm.2006.10.837 ↗
27. Pinna N, Grancharov S, Beato P, Bonville P, Antonietti M, Niederberger M (2005) Magnetite nanocrystals: nonaqueous synthesis characterization and solubility. Chem Mater 17:3044–304910.1021/cm050060+ ↗
28. Sellmyer DJ (2002) Strong magnets by self-assembly. Nature 420:374–37510.1038/420374a ↗
29. Sharma L, Kimura T (2003) FT-IR investigation into the miscible interactions in new materials for optical devices. Polym Adv Technol 14:392–39910.1002/pat.347 ↗
30. Sin SL, Gan LH, Hu X, Tam KC, Gan YY (2005) Photochemical and thermal isomerizations of azobenzene-containing amphiphilic diblock copolymers in aqueous micellar aggregates and in film. Macromolecules 38:3943–394810.1021/ma050097f ↗
31. Sun S, Murray CB, Weller D, Folks L, Moser A (2000) Monodisperse FePt nanoparticles and ferromagnetic FePt nanocrystal superlattices. Science 287:1989–199210.1126/science.287.5460.1989 ↗
32. Sun Y, Ding X, Zheng Z, Cheng X, Hu X, Peng Y (2007) Surface initiated ATRP in the synthesis of iron oxide/polystyrene core/shell nanoparticles. Eur Polym J 43:762–77210.1016/j.eurpolymj.2006.10.021 ↗
33. Teng X, Yang H (2003) Synthesis of face-centered tetragonal FePt nanoparticles and granular films from Pt@Fe2O3 core–shell nanoparticles. J Am Chem Soc 125:14559–1456310.1021/ja0376700 ↗
34. Teodorescu M, Matyjaszewski K (1999) Atom transfer radical polymerization of (Meth)acrylamides. Macromolecules 32:4826–483110.1021/ma990175x ↗
35. Veiseh O, Gunn JW, Zhang M (2010) Design and fabrication of magnetic nanoparticles for targeted drug delivery and imaging. Adv Drug Deliv Rev 62:284–30410.1016/j.addr.2009.11.002 ↗
36. Wang Y, Zhang M, Moers C, Chen S, Xu H, Wang Z, Zhang X, Li Z (2009) Block copolymer aggregates with photo-responsive switches: towards a controllable supramolecular container. Polymer 50:4821–482810.1016/j.polymer.2009.08.005 ↗
37. Winnik FM, Winnik MA, Tazuke S (1987) Interaction of hydroxypropylcellulose with aqueous surfactants: fluorescence probe studies and a look at pyrene-labeled polymer. J Phys Chem 91:594–59710.1021/j100287a021 ↗
38. Woo K, Hong J, Choi S, Lee HW, Ahn JP, Kim CS, Lee SW (2004) Easy synthesis and magnetic properties of iron oxide nanoparticles. Chem Mater 16:2814–281810.1021/cm049552x ↗
39. Yager KG, Barrett CJ (2006) Novel photo-switching using azobenzene functional materials. J Photochem Photobiol A 182:250–26110.1016/j.jphotochem.2006.04.021 ↗
40. Zhang J, Misra RDK (2007) Magnetic drug-targeting carrier encapsulated with thermo sensitive smart polymer: core–shell nanoparticle carrier and drug release response. Acta Biomater 3:838–85010.1016/j.actbio.2007.05.011 ↗
41. Zhao H, Shipp DA (2003) Preparation of poly(styrene-block-butyl acrylate) block copolymer-silicate nanocomposites. Chem Mater 15:2693–269510.1021/cm034013y ↗
42. Zhou Y, Wang S, Ding B, Yang Z (2008) Modification of magnetite nanoparticles via surface-initiated atom transfer radical polymerization (ATRP). Chem Eng J 138:578–58510.1016/j.cej.2007.07.030 ↗