Skip to main content
SpringerLink
Log in

Magnetite–polylactic acid nanoparticles by surface initiated organocatalysis ring opening polymerization

  • Research Paper
  • Published:
Journal of Nanoparticle Research Aims and scope Submit manuscript

Abstract

Organocatalysis by 4-N,N-dimethylaminopyridine was employed for ring opening polymerization of lactide initiated at magnetic nanoparticles covered by glycerol phosphate or ascorbic acid phosphate. The resulting magnetite–polylactic acid nanoparticles exhibit high colloidal stability in water and alcohol. Their morphology was investigated by transmission electron microscopy and the chemical structure was elucidated by Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy. The increase in mass after coating the nanoparticles was determined by thermogravimetric analysis, while dynamic light scattering revealed the increase in hydrodynamic size. Magnetic measurements revealed superparamagnetic behavior and high magnetization values. The magnetite–polylactic acid nanoparticles were further used for magnetic tagging of biotin.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 3
Fig. 9
Fig. 10

Similar content being viewed by others

References

  • Alexiou C, Jurgons R, Seliger G, Iro H (2006) Medical applications of magnetic nanoparticles. J Nanosci Nanotechnology 6(9–10):2762–2768. doi:10.1166/Jnn.2006.464

    Article  CAS  Google Scholar 

  • Bakandritsos A, Mattheolabakis G, Zboril R, Bouropoulos N, Tucek J, Fatouros DG, Avgoustakis K (2010) Preparation, stability and cytocompatibility of magnetic/PLA-PEG hybrids. Nanoscale 2(4):564–572. doi:10.1039/B9nr00253g

    Article  CAS  Google Scholar 

  • Dechy-Cabaret O, Martin-Vaca B, Bourissou D (2004) Controlled ring-opening polymerization of lactide and glycolide. Chem Rev 104(12):6147–6176. doi:10.1021/Cr040002s

    Article  CAS  Google Scholar 

  • Gijs MAM, Lacharme F, Lehmann U (2010) Microfluidic applications of magnetic particles for biological analysis and catalysis. Chem Rev 110(3):1518–1563. doi:10.1021/Cr9001929

    Article  CAS  Google Scholar 

  • Gomez-Lopera SA, Plaza RC, Delgado AV (2001) Synthesis and characterization of spherical magnetite/biodegradable polymer composite particles. J Colloid Interf Sci 240(1):40–47. doi:10.1006/jcis.2001.7579

    Article  CAS  Google Scholar 

  • Gomez-Lopera SA, Arias JL, Gallardo V, Delgado AV (2006) Colloidal stability of magnetite/poly(lactic acid) core/shell nanoparticles. Langmuir 22(6):2816–2821. doi:10.1021/La0530079

    Article  CAS  Google Scholar 

  • Hafeli UO, Sweeney SM, Beresford BA, Sim EH, Macklis RM (1994) Magnetically directed Poly(Lactic Acid) Y-90 microspheres-novel agents for targeted intracavitary radiotherapy. J Biomed Mater Res 28(8):901–908. doi:10.1002/jbm.820280809

    Article  CAS  Google Scholar 

  • Hafeli UO, Sweeney SM, Beresford BA, Humm JL, Macklis RM (1995) Effective targeting of magnetic radioactive Y-90 microspheres to tumor-cells by an externally applied magnetic-field-preliminary in vitro and in vivo results. Nucl Med Biol 22(2):147–155. doi:10.1016/0969-8051(94)00124-3

    Article  CAS  Google Scholar 

  • Ito A, Shinkai M, Honda H, Kobayashi T (2005) Medical application of functionalized magnetic nanoparticles. J Biosci Bioeng 100(1):1–11. doi:10.1263/Jbb.100.1

    Article  CAS  Google Scholar 

  • 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(6):2064–2110. doi:10.1021/Cr068445e

    Article  CAS  Google Scholar 

  • Li FX, Li XL, Li B (2011) Preparation of magnetic polylactic acid microspheres and investigation of its releasing property for loading curcumin. J Magn Magn Mater 323(22):2770–2775. doi:10.1016/j.jmmm.2011.05.045

    Article  CAS  Google Scholar 

  • Liu XQ, Novosad V, Rozhkova EA, Chen HT, Yefremenko V, Pearson J, Torno M, Bader SD, Rosengart AJ (2007) Surface functionalized biocompatible magnetic nanospheres for cancer hyperthermia. Ieee T Magn 43(6):2462–2464. doi:10.1109/Tmag.2007.894004

    Article  CAS  Google Scholar 

  • Lu R, Tao K, Sun K, Dou HJ, Xu B (2010) Facile synthesis of magnetic microcapsules by synchronous formation of magnetite nanoparticles. Colloid Polym Sci 288(3):353–357. doi:10.1007/s00396-009-2165-2

    Article  CAS  Google Scholar 

  • Massart R, Cabuil V (1987) Effect of some parameters on the formation of colloidal magnetite in alkaline-medium-yield and particle-size control. J Chim Phys PCB 84(7–8):967–973

    CAS  Google Scholar 

  • Nan A, Turcu R, Liebscher J (2012) Magnetite–polylactic acid core-shell nanoparticles by ring-opening polymerization under microwave irradiation. J Polym Sci Pol Chem 50(8):1485–1490. doi:10.1002/Pola.25920

    Article  CAS  Google Scholar 

  • Palumbo FS, Pitarresi G, Mandracchia D, Tripodo G, Giammona G (2006) New graft copolymers of hyaluronic acid and polylactic acid: synthesis and characterization. Carbohyd Polym 66(3):379–385. doi:10.1016/j.carbpol.2006.03.023

    Article  CAS  Google Scholar 

  • Prashant C, Dipak M, Yang CT, Chuang KH, Jun D, Feng SS (2010) Superparamagnetic iron oxide-loaded poly (lactic acid)-D-alpha-tocopherol polyethylene glycol 1000 succinate copolymer nanoparticles as MRI contrast agent. Biomaterials 31(21):5588–5597. doi:10.1016/j.biomaterials.2010.03.070

    Article  CAS  Google Scholar 

  • Ranganath KVS, Glorius F (2011) Superparamagnetic nanoparticles for asymmetric catalysis-a perfect match. Catal Sci Technol 1(1):13–22. doi:10.1039/C0cy00069h

    Article  CAS  Google Scholar 

  • Rothlingshofer M, Kervio E, Lommel T, Plutowski U, Hochgesand A, Richert C (2008) Chemical primer extension in seconds. Angew Chem Int Edit 47(32):6065–6068. doi:10.1002/anie.200801260

    Article  Google Scholar 

  • Shylesh S, Schünemann V, Thiel WR (2010) Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis. Angew Chem Int Edit 49(20):3428–3459. doi:10.1002/anie.200905684

    Article  CAS  Google Scholar 

  • Thammawong C, Sreearunothai P, Petchsuk A, Tangboriboonrat P, Pimpha N, Opaprakasit P (2012) Preparation and characterizations of naproxen-loaded magnetic nanoparticles coated with PLA-g-chitosan copolymer. J Nanopart Res 14(8):1046–1058. doi:10.1007/S11051-012-1046-7

    Article  Google Scholar 

  • Thomas CM (2010) Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures. Chem Soc Rev 39(1):165–173. doi:10.1039/B810065a

    Article  CAS  Google Scholar 

  • Vieira ID, Herres-Pawlis S (2012). Lactide polymerisation with complexes of neutral N-donors - new strategies for robust catalysts. Eur J Inorg Chem(5): 765–774. DOI 10.1002/ejic.201101131

  • Wang L, Neoh KG, Kang ET, Shuter B, Wang SC (2010) Biodegradable magnetic-fluorescent magnetite/poly(dl-lactic acid-co-alpha, beta-malic acid) composite nanoparticles for stem cell labeling. Biomaterials 31(13):3502–3511. doi:10.1016/j.biomaterials.2010.01.081

    Article  CAS  Google Scholar 

  • Yuan XB, Kang CS, Zhao YH, Gu MQ, Pu PY, Tian NJ, Sheng J (2009) Surface multi-functionalization of poly(lactic acid) nanoparticles and C6 glioma cell targeting in vivo. Chinese J Polym Sci 27(2):231–239

    Article  CAS  Google Scholar 

  • Zhao H, Saatchi K, Hafeli UO (2009) Preparation of biodegradable magnetic microspheres with poly(lactic acid)-coated magnetite. J Magn Magn Mater 321(10):1356–1363. doi:10.1016/j.jmmm.2009.02.038

    Article  CAS  Google Scholar 

  • Zhou SB, Sun J, Sun L, Dai YQ, Liu LP, Li XH, Wang JX, Weng J, Jia WX, Zhang ZR (2008) Preparation and characterization of interferon-loaded magnetic biodegradable microspheres. J Biomed Mater Res B 87B(1):189–196. doi:10.1002/Jbm.B.31091

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors wish to acknowledge Dr. Ioan Bratu for FTIR measurements, Dr. Cristian Leostean for conducting magnetic measurements, Dr. Lucian Barbu for TEM investigations, Camelia Daia for DLS measurements. This study was supported by the Romanian Ministry of Education and Research under the research project PN-II-RU-TE-2011-3-0130.

Author information

Authors and Affiliations

  1. National Institute of R&D for Isotopic and Molecular Technologies, Donath 65-103, 400293, Cluj-Napoca, Romania

    Alexandrina Nan & Rodica Turcu

  2. Institute of Chemistry, Humboldt-University Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany

    Joachim Leistner

Authors
  1. Alexandrina Nan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joachim Leistner
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rodica Turcu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rodica Turcu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nan, A., Leistner, J. & Turcu, R. Magnetite–polylactic acid nanoparticles by surface initiated organocatalysis ring opening polymerization. J Nanopart Res 15, 1869 (2013). https://doi.org/10.1007/s11051-013-1869-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11051-013-1869-x

Keywords

Search

Navigation