Hydrophilic azlactone-functionalized magnetite nanoparticle for conjugation with folic acid
Source abstract
Abstract
Herein, we report the synthesis of magnetite nanoparticles (MNPs) grafted with poly(poly(ethylene glycol) methyl ether methacrylate-stat-2-vinyl-4,4-dimethylazlactone) copolymers (poly(PEGMA-stat-VDM)) prepared via a surface-initiated atom transfer radical polymerization (ATRP) and used for the immobilization of folic acid (FA). The MNPs were synthesized using a thermal decomposition method and surface functionalized to obtain ATRP-initiating sites. The particle size was in the range of 5–10 nm with the average of 8.0 ± 1.2 nm in diameter. Molar ratio of PEGMA to VDM was systematically varied (0/100, 30/70, 50/50, and 70/30, respectively) in the copolymerization to obtain water dispersible MNP with various amounts of azlactone rings, an electrophilic moiety, on its surface. Grafting density of VDM on the particle surface increased with increased VDM loading in the copolymerization reaction. These copolymer-coated MNPs were well dispersible in water with some nano-scale aggregation after FA functionalization due to hydrophobic character of FA. Since FA is a cancer cell targeting agent, it is anticipated that these novel FA-functionalized MNPs could be used as magnetically guidable vehicle for drug delivery, particularly for cancer treatment. The results of this study warrant a future investigation of this promising system.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanoparticle-Based Drug Delivery · Advanced Polymer Synthesis and Characterization · Polymer Surface Interaction Studies
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References (44)
Show source-provided references
1. Ahmad H, Rahman MA, Miah MAJ, Tauer K (2008) Magnetic and temperature-sensitive composite polymer particles and adsorption behavior of emulsifiers and trypsin. Macromol Res 16:637–64310.1007/BF03218573 ↗
2. Aqil A, Vasscur S, Duguct E, Passirani C, Benoît JP, Roch A, Müller R, Jérôme R, Jérôme C (2008) PEO coated magnetic nanoparticles for biomedical application. Eur Polym J 44:3191–319910.1016/j.eurpolymj.2008.07.011 ↗
3. Chen D, Jiang M, Li N, Gu H, Xu Q, Ge J, Xia X, Lu J (2010) Modification of magnetic silica/iron oxide nanocomposites with fluorescent polymethacrylic acid for cancer targeting and drug delivery. J Mater Chem 20:6422–642910.1039/c0jm00320d ↗
4. Ciampolini M, Nardi N (1966) Five-coordinated high-spin complexes of bivalent cobalt, nickel and copper with tris(2-dimethylaminoethyl)amine. Inorg Chem 5:41–4310.1021/ic50035a010 ↗
5. Culita DC, Patron L, Oprea O, Bartha C, Palade P, Teodorescu V, Filoti G (2013) Detailed characterization of functionalized magnetite and ascertained effects. J Nanopart Res 15:1–1510.1007/s11051-013-1916-7 ↗
6. Dong H, Huang J, Koepsel RR, Ye P, Russell AJ, Matyjaszewski K (2011) Recyclable antibacterial magnetic nanoparticles grafted with quaternized poly(2-(dimethylamino) ethyl methacrylate) brushes. J Am Chem Soc 12:1305–1311
7. Ebrahiminezhad A, Ghasemi Y, Rasoul-Amini S, Barar J, Davaran S (2013) Preparation of novel magnetic fluorescent nanoparticles using amino acids. Colloids Surf B 102:534–53910.1016/j.colsurfb.2012.08.046 ↗
8. Fu A, Hu W, Xu L, Wilson RJ, Yu H, Osterfeld SJ, Gambhir SS, Wang SX (2009) Protein-functionalized synthetic antiferromagnetic nanoparticles for biomolecule detection and magnetic manipulation. Angew Chem Int Ed Engl 48:1620–162410.1002/anie.200803994 ↗
9. Ho TH, Levere M, Soutif JC, Montembault V, Pascual S, Fontaine L (2010) Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition “click” chemistry. Polym Chem 2:1258–1260
10. Horák D, Chekina N (2006) Preparation of magnetic poly(glycidyl methacrylate) microspheres by emulsion polymerization in the presence of sterically stabilized iron oxide nanoparticles. J Appl Polym Sci 102:4348–435710.1002/app.24923 ↗
11. Jenkins SI, Pickard MR, Granger N, Chari DM (2011) Magnetic nanoparticle-mediated gene transfer to oligodendocyte precursor cell transplant populations is enhanced by magnetofection strategies. ACS Nano 5:6527–653810.1021/nn2018717 ↗
12. Johnson PA, Park HJ, Driscoll AJ (2011) Enzyme nanoparticle fabrication: magnetic nanoparticle synthesis and enzyme immobilization. Methods Mol Biol 679:183–19110.1007/978-1-60761-895-9_15 ↗
13. Kang K, Choi J, Nam JH, Lee SC, Kim KJ, Lee SW, Chang JH (2009) Preparation and characterization of chemically functionalized silica-coated magnetic nanoparticles as a DNA separator. J Phys Chem B 113:536–54310.1021/jp807081b ↗
14. Khodadust R, Unsoy G, Yalcm S, Gunduz G, Gunduz U (2013) PAMAM dendrimer-coated iron oxide nanoparticles: synthesis and characterization of different generations. J Nanopart Res 15:1–13
15. Lacerda PSS, Barros-Timmons AMMV, Freire CSR, Silvestre AJD, Neto CP (2013) Nanostructured composites obtained by ATRP sleeving of bacterial cellulose nanofibers with acrylate polymers. Biomacromolecules 14:2063–207310.1021/bm400432b ↗
16. Levere ME, The Ho H, Pascual S, Fontaine L (2011) Stable azlactone-functionalized nanoparticles prepared from thermoresponsive copolymers synthesized by RAFT polymerization. Polym Chem 2:2878–288710.1039/c1py00320h ↗
17. Lin JJ, Chen JS, Huang SJ, Ko JH, Wang YM, Chen TL, Wang LF (2009) Folic acid–pluronic F127 magnetic nanoparticle clusters for combined targeting, diagnosis, and therapy applications. Biomaterials 30:5114–512410.1016/j.biomaterials.2009.06.004 ↗
18. Low PS, Henne WA, Doorneweerd DD (2008) Discovery and development of folic-acid-based receptor targeting for imaging and therapy of cancer and inflammatory diseases. Acc Chem Res 41:120–12910.1021/ar7000815 ↗
19. Lu X, Zhang L, Meng L, Liu Y (2007) Synthesis of poly(N-isopropylacrylamide) by ATRP using a fluorescein-based initiator. Polym Bull 59:195–20610.1007/s00289-007-0754-0 ↗
20. Mauricio MR, Otsuka I, Borsali R, Petzhold CL, Cellet TSP, de Maria Carvalho G, Rubira AF (2011) Synthesis of star poly(N-isopropylacrylamide) by β-cyclodextrin core initiator via ATRP approach in water. React Funct Polym 71:1160–116510.1016/j.reactfunctpolym.2011.09.004 ↗
21. Mendonça PV, Serra AC, Coelho JFJ, Popov AV, Guliashvili T (2011) Ambient temperature rapid ATRP of methyl acrylate, methyl methacrylate and styrene in polar solvents with mixed transition metal catalyst system. Eur Polym J 47:1460–146610.1016/j.eurpolymj.2011.03.014 ↗
22. Mohapatra S, Mallick SK, Maiti TK, Ghosh SK, Pramanik P (2007) Synthesis of highly stable folic acid conjugated magnetite nanoparticles for targeting cancer cells. Nanotechnology 18:1–9
23. Mosivand S, Monzon LMA, Ackland K, Kazeminezhad I, Coey JMD (2013) The effect of organics on the structure and magnetization of electro-synthesised magnetite nanoparticles. J Nanopart Res 15:1–1110.1007/s11051-013-1795-y ↗
24. Narain R, Gonzales M, Hoffman AS, Stayton PS, Krishnan KM (2007) Synthesis of monodisperse biotinylated p(NIPAAm)-coated iron oxide magnetic nanoparticles and their bioconjugation to streptavidin. Langmuir 23:6234–6299
25. Pothayee N, Balasubramaniam S, Davis RM, Riffle JS, Carroll MRJ, Woodward RC, St Pierre TG (2011) Synthesis of ‘ready-to-adsorb’ polymeric nanoshells for magnetic iron oxide nanoparticles via atom transfer radical polymerization. Polymer 52:1356–136610.1016/j.polymer.2011.01.047 ↗
26. Prai-in Y, Tankanya K, Rutnakornpituk B, Wichai U, Montembault V, Pascual S, Fontaine L, Rutnakornpituk M (2012) Azlactone functionalization of magnetic nanoparticles using ATRP and their bioconjugation. Polymer 53:113–12010.1016/j.polymer.2011.11.021 ↗
27. Qu H, Ma H, Zhou W, O’Connor CJ (2012) In situ surface functionalization of magnetic nanoparticles with hydrophilic natural amino acids. Inorg Chim Acta 389:60–6510.1016/j.ica.2012.01.058 ↗
28. Rutnakornpituk M, Puangsin N, Theamdee P, Rutnakornpituk B, Wichai U (2011) Poly(acrylic acid)-grafted magnetic nanoparticle for conjugation with folic acid. Polymer 52:987–99510.1016/j.polymer.2010.12.059 ↗
29. Sahu SK, Maiti S, Pramanik A, Ghosh SK, Pramanik P (2012) Controlling the thickness of polymeric shell on magnetic nanoparticles loaded with doxorubicin for targeted delivery and MRI contrast agent. Carbohydr Polym 87:2593–260410.1016/j.carbpol.2011.11.033 ↗
30. Sarkar TR, Irudayaraj J (2008) Carboxyl-coated magnetic nanoparticles for mRNA isolation and extraction of supercoiled plasmid DNA. Anal Biochem 379:130–13210.1016/j.ab.2008.04.016 ↗
31. Sauzedde F, Elaissari A, Pichot C (1999a) Hydrophilic magnetic polymer latexes 1. Adsorption of magnetic iron oxide nanoparticles onto various cationic latexes. Colloid Polym Sci 277:846–85510.1007/s003960050461 ↗
32. Sauzedde F, Elaissari A, Pichot C (1999b) Hydrophilic magnetic polymer latexes 2. Encapsulation of adsorbed iron oxide nanoparticles. Colloid Polym Sci 277:1041–105010.1007/s003960050488 ↗
33. Sun C, Sze R, Zhang M (2006) Folic acid-PEG conjugated superparamagnetic nanoparticles for targeted cellular uptake and detection by MRI. J Biomed Mater Res A 78:550–55710.1002/jbm.a.30781 ↗
34. 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 ↗
35. Taylor LD, Kolesinski HS, Mehta AC, Locatell L, Larson PS (1982) Synthesis of poly(4,4-dimethyl-2-vinyl-5-oxazolone) an interesting material for preparing polymeric agent. Makromol Chem Rapid Commun 3:779–78210.1002/marc.1982.030031105 ↗
36. Viota JL, Carazo A, Munoz-Gamez JA, Rudzka K, Gómez-Sotomayor R, Ruiz-Extremera A, Salmerón J, Delgado AV (2013) Functionalized magnetic nanoparticles as vehicles for the delivery of the antitumor drug gemcitabine to tumor cells. Physiochemical in vitro evaluation. Mater Sci Eng C 33:1183–119210.1016/j.msec.2012.12.009 ↗
37. Wang TH, Lee WC (2003) Immobilization of proteins on magnetic nanoparticles. Biotechnol Bioprocess Eng 8:263–26710.1007/BF02942276 ↗
38. Wang F, Shen H, Feng J, Yang H (2006) PNA-modified magnetic nanoparticles and their hybridization with single-stranded DNA target: surface enhanced Raman scatterings study. Microchim Acta 153:15–2010.1007/s00604-005-0460-2 ↗
39. Wang H, Luo W, Chen J (2012) Fabrication and characterization of thermoresponsive Fe3O4@PNIPAM hybrid nanomaterials by surface-initiated RAFT polymerization. J Mater Sci 47:5918–592510.1007/s10853-012-6493-0 ↗
40. Wang N, Guan Y, Yang L, Jia L, Wei X, Liu H, Guo C (2013) Magnetic nanoparticles (MNPs) covalently coated by PEO–PPO–PEO block copolymer for drug delivery. J Colloid Interface Sci 395:50–5710.1016/j.jcis.2012.11.062 ↗
41. Yallapu MM, Othman SF, Curtis ET, Gupta BK, Jaggi M, Chauhan SC (2012) Multi-functional magnetic nanoparticles for magnetic resonance imaging and cancer therapy. Biomaterials 32:1890–190510.1016/j.biomaterials.2010.11.028 ↗
42. Yang HM, Park CW, Bae PK, Ahn T, Seo BK, Chung BH, Kim JD (2013) Folate-conjugated cross-linked magnetic nanoparticles as potential magnetic resonance probes for in vivo cancer imaging. J Mater Chem B 1:3035–304310.1039/c3tb20295j ↗
43. Yu S, Wu G, Gu X, Wang J, Wang Y, Gao H, Ma J (2013) Magnetic and pH-sensitive nanoparticles for antitumor drug delivery. Colloids Surf B 103:15–2210.1016/j.colsurfb.2012.10.041 ↗
44. 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 ↗