journal article·2014-12

One-pot synthesis of biocompatible boronic acid-functionalized poly(methyl methacrylate) nanoparticles at sub-100 nm scale for glucose sensing

Huseyin Sakalak, Mehmet Ulasan, Emine Yavuz, Sevket Tolga Camli, Mustafa Selman Yavuz

Journal of Nanoparticle Research· Volume 16· Issue 12
Publisher page

Abstract

Poly(methyl methacrylate) nanoparticles containing 4-vinylphenyl boronic acid were synthesized in one pot by surfactant-free emulsion polymerization. The nanoparticles were characterized by scanning electron microscopy and dynamic light scattering. Boron content in the nanoparticles was confirmed by electron-dispersive X-ray spectroscopy. In polymerization process, several co-monomer ratios were studied in order to obtain optimum nanoparticle size. Average hydrodynamic diameter and polydispersity index of nanoparticles versus variation of acetone percentage in the solvent mixture and total monomer concentration were investigated. The effect of boronic acid concentration in the monomer mixture on nanoparticle size and size distribution was also reported. Without further functionalization to the nanoparticles, the catechol dye, alizarin red S, was bound to boronic acid-containing nanoparticles. These nanoparticles behave as a nanosensor by which glucose or fructose can be easily detected. Dye-containing nanoparticles were undertaken displacement reaction by glucose or fructose. The glucose or fructose content was also monitored by UV–Visible spectrophotometer. Furthermore, cytotoxicity studies of boronic acid-carrying poly(methyl methacrylate) nanoparticles were carried out in 3T3 cells, which showed no toxicity effect on the cells.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Analytical Chemistry and Sensors · Advanced Polymer Synthesis and Characterization · Mass Spectrometry Techniques and Applications

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References (51)

Show source-provided references
1. Amigoni-Gerbier S, Larpent C (1999) Synthesis and properties of selective metal-complexing nanoparticles. Macromolecules 32:9071–907310.1021/ma991254b ↗
2. Amigoni-Gerbier S, Desert S, Gulik-Kryswicki T, Larpent C (2002) Ultrafine selective metal-complexing nanoparticles: synthesis by microemulsion copolymerization, binding capacity, and ligand accessibility. Macromolecules 35:1644–165010.1021/ma0113632 ↗
3. Arimori S, Ward CJ, James TD (2002) A d-glucose selective fluorescent assay. Tetrahedron Lett 43:303–30510.1016/S0040-4039(01)02102-5 ↗
4. Bao J, Zhang A (2004) Poly(methyl methacrylate) nanoparticles prepared through microwave emulsion polymerization. J Appl Polym Sci 93:2815–282010.1002/app.20758 ↗
5. Billingsley K, Balaconis MK, Dubach JM, Zhang N, Lim E, Francis KP, Clark HA (2010) Fluorescent nano-optodes for glucose detection. Anal Chem 82(9):3707–371310.1021/ac100042e ↗
6. Camli ST, Buyukserin F, Balci O, Budak GG (2010a) Size controlled synthesis of sub-100 nm monodisperse poly(methylmethacrylate) nanoparticles, using surfactant-free emulsion polymerization. J Colloid Interface Sci 344:528–53210.1016/j.jcis.2010.01.041 ↗
7. Camli ST, Buyukserin F, Yavuz MS, Budak GG (2010b) Fine-tuning of functional poly(methylmethacrylate) nanoparticle size at the sub-100 nm scale using surfactant-free emulsion polymerization. Colloids Surf A 366:141–14610.1016/j.colsurfa.2010.05.037 ↗
8. Cannizzo C, Sonia AG, Larpent C (2005) Boronic acid-functionalized nanoparticles: synthesis by microemulsion polymerization and application as a re-usable optical nanosensor for carbohydrates. Polymer 46:1269–127910.1016/j.polymer.2004.11.052 ↗
9. Catauro M, Papale F, Roviello G, Ferone C, Bollino F, Trifuoggi M, Aurilio C (2013) Synthesis of SiO2 and CaO rich calcium silicate systems via sol-gel process: bioactivity, biocompatibility, and drug delivery tests. J Biomed Mater Res, Part A. doi: 10.1002/jbm.a.34978
10. Chen KY, Chen YW (2003) Synthesis of spherical titanium dioxide particles by homogeneous precipitation in acetone solution. J Sol–Gel Sci Technol 27:111–11710.1023/A:1023738215053 ↗
11. Choi CH, Jung JH, Rhee YW, Kim DP, Shim SE, Lee CS (2007) Generation of monodisperse alginate microbeads and in situ encapsulation of cell in microfluidic device. Biomed Microdevices 9:855–86210.1007/s10544-007-9098-7 ↗
12. Choi CH, Jung JH, Hwang TS, Lee CS (2009) In Situ microfluidic synthesis of monodisperse PEG microspheres. Macromol Res 17:163–16710.1007/BF03218673 ↗
13. Cicek H (2005) Nucleotide isolation by boronic acid functionalized hydrogel beads. J Bioact Compat Pol 20:245–25710.1177/0883911505053376 ↗
14. Congur G, Sayar F, Erdem A, Piskin E (2013) Voltammetric and impedimetric DNA detection at single-use graphite electrodes modified with gold nanorods. Colloids Surf B: Biointerfaces 112:61–6610.1016/j.colsurfb.2013.07.040 ↗
15. Coskun A, Akkaya EU (2004) Three-point recognition and selective fluorescence sensing of L-DOPA. Org Lett 6:3107–310910.1021/ol0488744 ↗
16. Cui F, Qian F, Zhao Z, Yin L, Tang C, Yin C (2009) Preparation, characterization, and oral delivery of insulin loaded carboxylated chitosan grafted poly(methyl methacrylate) nanoparticles. Biomacromolecules 10:1253–125810.1021/bm900035u ↗
17. Fan L, Luo C, Sun M, Qiu H, Li X (2013) Synthesis of magnetic β-cyclodextrin–chitosan/graphene oxide as nanoadsorbent and its application in dye adsorption and removal. Colloids Surf B: Biointerfaces 103:601–60710.1016/j.colsurfb.2012.11.023 ↗
18. Fei J, Wu K, Wang F, Hu S (2004) Glucose nanosensors based on redox polymer/glucose oxidase modified carbon fiber nanoelectrodes. Talanta 65:918–92410.1016/j.talanta.2004.08.015 ↗
19. Goldshtein J, Margel S (2009) Synthesis and characterization of new UV absorbing microspheres of narrow size distribution by dispersion polymerization of 2-(2′-hydroxy-5′-methacryloxyethylphenyl)-2H-benzotriazole. Polymer 50:3422–343010.1016/j.polymer.2009.05.056 ↗
20. Hazra C, Kundu D, Chatterjee A, Chaudhari A, Mishra S (2014) Biopolymer and biosurfactant-graft-calcium sulfate/polystyrene nanocomposites: thermophysical, mechanical and biodegradation studies. Colloids and Surfaces A: Physicochem Eng Aspects 449:96–11310.1016/j.colsurfa.2014.02.051 ↗
21. Hoare T, Pelton R (2007) Engineering glucose swelling responses in poly(N-isopropylacrylamide)-based microgels. Macromolecules 40:670–67810.1021/ma062254w ↗
22. Huang YJ, Jiang YB, Fossey JS, James TD, Marken F (2010) Assembly of N-hexadecyl-pyridinium-4-boronic acid hexafluorophosphate monolayer films with catechol sensing selectivity. J Mater Chem 20:8305–831010.1039/c0jm01510e ↗
23. Hurkat P, Jain A, Jain A, Shilpi S, Gulbake A, Jain KS (2012) Concanavalin A conjugated biodegradable nanoparticles for oral insulin delivery. J Nanopart Res 14(1219):1–14
24. Ivanov AE, Galaev IY, Mattiasson B (2005) Binding of adenosine to pendant phenylboronate groups of thermoresponsive copolymer: a quantitative study. Macromol Biosci 5:795–80010.1002/mabi.200500035 ↗
25. Ivanov AE, Kumar A, Nilsang S, Aguilar MR, Mikhalovska LI, Savina IN, Nilsson L, Scheblykin IG, Kuzimenkova MV, Galaev IY (2010) Evaluation of boronate-containing polymer brushes and gels as substrates for carbohydrate-mediated adhesion and cultivation of animal cells. Colloids Surf B: Biointerfaces 75:510–51910.1016/j.colsurfb.2009.09.028 ↗
26. James TD (2007) Saccharide-selective boronic acid based photoinduced electron transfer (PET) fluorescent sensors. Top Curr Chem 277:107–15210.1007/128_2007_110 ↗
27. Jia L, Lv LP, Xu JP, Jian J (2011) Phosphorylcholine functionalized dendrimers for the formation of highly stable and reactive gold nanoparticles and their glucose conjugation for biosensing. J Nanopart Res 13:4075–408310.1007/s11051-011-0351-x ↗
28. Lapeyre V, Ancla C, Catargi B, Ravaine V (2008) Glucose-responsive microgels with a core-shell structure. J Colloid Interface Sci 327:316–32310.1016/j.jcis.2008.08.039 ↗
29. Liu Y, Zhang Y, Zhao Y, Yu J (2014) Phenylboronic acid polymer brush-enabled oriented and high density antibody immobilization for sensitive microarray immunoassay. Colloids Surf B: Biointerfaces 121:21–2610.1016/j.colsurfb.2014.05.031 ↗
30. Lu W, Qin X, Asiri AM, Al-Youbi AO, Sun X (2013) Green synthesis of carbon nanodots as an effective fluorescent probe for sensitive and selective detection of mercury(II) ions. J Nanopart Res 15(1344):1–7
31. Luhana C, Bo XJ, Ju J, Guo LP (2012) A novel enzymatic glucose sensor based on Pt nanoparticles-decorated hollow carbon spheres-modified glassy carbon electrode. J Nanopart Res 14(1158):1–9
32. Matsumoto A, Ikeda S, Harada A, Kataoka K (2003) Glucose-responsive polymer bearing a novel phenylborate derivative as a glucose-sensing moiety operating at physiological pH conditions. Biomacromolecules 4:1410–141610.1021/bm034139o ↗
33. Niemeyer CM (2001) Nanoparticles, proteins, and nucleic acids: biotechnology meets materials science. Angew Chem Int Ed 40:4128–415810.1002/1521-3773(20011119)40:22<4128::AID-ANIE4128>3.0.CO;2-S ↗
34. Okasaka Y, Kitano H (2010) Direct spectroscopic observation of binding of sugars to polymers having phenylboronic acids substituted with an ortho-phenylazo group. Colloids Surf B: Biointerfaces 79:434–43910.1016/j.colsurfb.2010.05.015 ↗
35. Ormsby R, McNally T, O’Hare P, Burke G, Mitchell C, Dunne N (2012) Fatigue and biocompatibility properties of a poly(methyl methacrylate) bone cement with multi-walled carbon nanotubes. Acta Biomater 8:1201–121210.1016/j.actbio.2011.10.010 ↗
36. Pickup JC, Hussain F, Evans ND, Rolinski OJ, Birch DJS (2005) Fluorescence-based glucose sensors. Biosens Bioelectron 20:2555–256510.1016/j.bios.2004.10.002 ↗
37. Sheikh FA, Ju HW, Moon BM, Park HJ, Kim JH, Lee OJ, Park CH (2013) Facile and highly efficient approach for the fabrication of multifunctional silk nanofibers containing hydroxyapatite and silver nanoparticles. J Biomed Mater Res Part A. doi: 10.1002/jbm.a.35024
38. Springsteen G, Wang B (2001) Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates. Chem Commun 17:1608–160910.1039/b104895n ↗
39. Springsteen G, Wang B (2002) Detailed examination of boronic acid-diol complexation. Tetrahedron 58:5291–530010.1016/S0040-4020(02)00489-1 ↗
40. Tamer U, Gundogdu Y, Boyaci IH, Pekmez K (2010) Synthesis of magnetic core–shell Fe3O4–Au nanoparticle for biomolecule immobilization and detection. J Nanopart Res 12:1187–119610.1007/s11051-009-9749-0 ↗
41. The diabetes control and complications trial research group (1997) Hypoglycemia in the diabetes control and complications trial. Diabetes 46:271–28610.2337/diab.46.2.271 ↗
42. Uguzdogan E, Kayi H, Denkbas EB, Patir S, Tuncel A (2003) Stimuli-responsive properties of aminophenylboronic acid carrying thermosensitive copolymers. Polym Int 52:649–65710.1002/pi.1169 ↗
43. Vollrath A, Pretzel D, Pietsch C, Perevyazko I, Schubert S, Pavlov GM, Schubert US (2012) Preparation, cellular internalization, and biocompatibility of highly fluorescent PMMA nanoparticles. Macromol Rapid Commun 33:1791–179710.1002/marc.201200329 ↗
44. Wang S, Guo Z (2014) Bio-inspired encapsulation and functionalization of living cells with artificial shells. Colloids Surf B: Biointerfaces 113:483–50010.1016/j.colsurfb.2013.09.024 ↗
45. Wu W, Mitra N, Yan ECY, Zhou S (2010) Multifunctional hybrid nanogel for integration of optical glucose Sensing and self-regulated insulin release at physiological Ph. ACS Nano 4(8):4831–483910.1021/nn1008319 ↗
46. Xu K, Qiu Q, Jiang J, Yang X (2005) Non-invasive glucose sensing with near-infrared spectroscopy enhanced by optical measurement conditions reproduction technique. Opt Lasers Eng 43:1096–110610.1016/j.optlaseng.2004.06.018 ↗
47. Xuewen H, Nan M (2014) An overview of recent advance of quantum dots for biomedical applications. Biointerfaces, Colloids Surf B. doi: 10.1016/j.colsurfb.2014.06.002
48. Yan J, Springsteen G, Deeter S, Wang B (2004) The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols-it is not as simple as it appears. Tetrahedron 60:11205–1120910.1016/j.tet.2004.08.051 ↗
49. Yan HB, Zhang YQ, Ma YL, Zhou LX (2009) Biosynthesis of insulin-silk fibroin nanoparticles conjugates and in vitro evaluation of a drug delivery system. J Nanopart Res 11:1937–194610.1007/s11051-008-9549-y ↗
50. Yang X, Bakaic E, Hoare T, Cranston ED (2013) Injectable polysaccharide hydrogels reinforced with cellulose nanocrystals: morphology, rheology, degradation, and cytotoxicity. Biomacromolecules 14:4447–445510.1021/bm401364z ↗
51. Yavuz MS, Buyukserin F, Zengin Z, Camli ST (2011) Thermoresponsive oligo(ethylene glycol) methacrylate colloids with antifouling surface properties. J Polym Sci A Polym Chem 49:4800–480810.1002/pola.24927 ↗