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Bivalent alkyne-bisphosphonate as clickable and solid anchor to elaborate multifunctional iron oxide nanoparticles with microwave enhancement

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Abstract

We report the elaboration of clickable superparamagnetic nanoparticles that act as a scaffold for further modifications by click chemistry. This nano platform is easily obtained by coating iron oxide nanoparticle γ-Fe2O3, with a new bifunctional molecule (1-hydroxy-1-phosphonopent-4-ynyl)phosphonic acid (HMBPyne). The HMBP and the alkyne functions act respectively as anchoring surface group and click chemistry functionality. We evaluate the functionalization of this new “clickable” nanoplateform using Huisgen 1,3-cycloaddition as model reaction and demonstrate the potential of microwave irradiation to increase the grafting yield. The effectiveness of click chemistry for the modification of mNPs is explored with a diverse array of functional species.

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References

  • Algar WR, Prasuhn DE, Stewart MH, Jennings TL, Blanco-Canosa JB, Dawson PE, Medintz IL (2011) The controlled display of biomolecules on nanoparticles: a challenge suited to bioorthogonal chemistry. Bioconj Chem 22(5):825–858. doi:10.1021/bc200065z

    Article  CAS  Google Scholar 

  • Amstad E, Gillich T, Bilecka I, Textor M, Reimhult E (2009) Ultra stable iron oxide nanoparticle colloidal suspensions using dispersants with catechol-derived anchor groups. Nano Lett 9(12):4042–4048. doi:10.1021/nl902212q

    Article  CAS  Google Scholar 

  • Baruwati B, Nadagouda MN, Varma RS (2008) Bulk synthesis of monodisperse ferrite nanoparticles at water−organic interfaces under conventional and microwave hydrothermal treatment and their surface functionalization. J Phys Chem C 112(47):18399–18404. doi:10.1021/jp807245g

    CAS  Google Scholar 

  • Basti H, Ben Tahar L, Smiri LS, Herbst F, Vaulay MJ, Chau F, Ammar S, Benderbous S (2011) Catechol derivatives-coated Fe3O4 and γ-Fe2O3 nanoparticles as potential MRI contrast agents. J Colloid Interface Sci 341(2):248–254

    Article  Google Scholar 

  • Benyettou F, Lalatonne Y, Sainte-Catherine O, Monteil M, Motte L (2009) Super paramagnetic nano vector with anti-cancer properties: γFe2O3@Zoledronate. Int J Pharm 379(2):324–327

    Article  CAS  Google Scholar 

  • Benyettou F, Guénin E, Lalatonne L, Motte L (2011) Microwave assisted nano particle surface functionalization. Nanotechnology 22(5):055102

    Article  CAS  Google Scholar 

  • Bertorelle F, Wilhelm C, Roger J, Gazeau F, Ménager C, Cabuil V (2006) Fluorescence-modified super paramagnetic nanoparticles: intracellular uptake and use in cellular imaging. Langmuir 22(12):5385–5391. doi:10.1021/la052710u

    Article  CAS  Google Scholar 

  • Bilecka I, Djerdj I, Niederberger M (2008) One-minute synthesis of crystalline binary and ternary metal oxide nanoparticles. Chem Commun 21(7):886–888

    Article  Google Scholar 

  • Bouillon C, Meyer A, Vidal S, Jochum A, Chevolot Y, Cloarec J-P, Praly J-P, Vasseur J-J, Morvan F (2006) Microwave assisted “click” chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support. J Org Chem 71:4700–4702

    Article  CAS  Google Scholar 

  • Chen X, Gambhir SS, Cheon J (2011) Theranostic nanomedicine. Acc Chem Res 44(10):841–1134. doi:10.1021/ar200231d Special issue on theranostic nanomedecine

    Article  CAS  Google Scholar 

  • Dave SR, Gao X (2009) Monodisperse magnetic nanoparticles for biodetection, imaging, and drug delivery: a versatile and evolving technology. Wiley Interdiscip Rev Nanomed Nanobiotechnol 1(6):583–609. doi:10.1002/wnan.51

    Article  CAS  Google Scholar 

  • Dubertret B, Calame M, Libchaber AJ (2001) Single-mismatch detection using gold-quenched fluorescent oligonucleotides. Nat Biotechnol 19:365–370

    Article  CAS  Google Scholar 

  • Guénin E, Monteil M, Bouchemal N, Prangé T, Lecouvey M (2007) Syntheses of phosphonic esters of alendronate, pamidronate and neridronate. Eur J Org Chem 20:3380–3391

    Article  Google Scholar 

  • Haun JB, Yoon T-J, Lee H, Weissleder R (2010) Magnetic nano particle biosensors. Wiley Interdiscip Rev Nanomed Nanobiotechnol 2(3):291–304. doi:10.1002/wnan.84

    Article  CAS  Google Scholar 

  • Karimi A, Denizot B, Hindré F, Filmon R, Greneche J-M, Laurent S, Daou T, Begin-Colin S, Le Jeune J-J (2010) Effect of chain length and electrical charge on properties of ammonium-bearing bisphosphonate-coated super paramagnetic iron oxide nanoparticles: formulation and physicochemical studies. J Nanopart Res 12(4):1239–1248. doi:10.1007/s11051-009-9815-7

    Article  CAS  Google Scholar 

  • Lalatonne Y, Paris C, Serfaty JM, Weinmann P, Lecouvey M, Motte L (2008) Bis-phosphonates-ultra small super paramagnetic iron oxide nanoparticles: a platform towards diagnosis and therapy. Chem Commun 14(22):2553–2555

    Article  Google Scholar 

  • Li N, Binder WH (2011) Click-chemistry for nano particle-modification. J Mater Chem 21(42):16717–16734

    Article  CAS  Google Scholar 

  • Mandal SK, Lequeux N, Rotenberg B, Tramier M, Fattaccioli J, Bibette J, Dubertret B (2005) Encapsulation of magnetic and fluorescent nanoparticles in emulsion droplets. Langmuir 21(9):4175–4179. doi:10.1021/la047025m

    Article  CAS  Google Scholar 

  • Martin A, Hickey J, Ablack A, Lewis J, Luyt L, Gillies E (2010) Synthesis of bombesin-functionalized iron oxide nanoparticles and their specific uptake in prostate cancer cells. J Nanopart Res 12(5):1599–1608. doi:10.1007/s11051-009-9681-3

    Article  CAS  Google Scholar 

  • McCarthy JR, Weissleder R (2008) Multifunctional magnetic nanoparticles for targeted imaging and therapy. Adv Drug Deliv Rev 60(11):1241–1251

    Article  CAS  Google Scholar 

  • Meldal M, Tornoe CW (2008) Cu-catalyzed azide-alkyne cycloaddition. Chem Rev 108(8):2952–3015. doi:10.1021/cr0783479

    Article  CAS  Google Scholar 

  • Migianu E, Guénin E, Lecouvey M (2005) New efficient synthesis of 1-hydroxymethylene-1,1-bisphosphonic monomethyl esters. Synlett 5:0425–0428

    Google Scholar 

  • Milosevic I, Jouni H, David C, Warmont F, Bonnin D, Motte L (2011) Facile microwave process in water for the fabrication of magnetic nano rods. J Phys Chem C 115(39):18999–19004. doi:10.1021/jp205334v

    Article  CAS  Google Scholar 

  • Motte L, Benyettou F, de Beaucorps C, Lecouvey M, Milesovic I, Lalatonne Y (2010) Multimodal super paramagnetic nanoplatform for clinical applications: immunoassays, imaging & therapy. Faraday Discuss 149:211–225

    Article  Google Scholar 

  • Moumen N, Veillet P, Pileni MP (1995) Controlled preparation of nano size cobalt ferrite magnetic particles. J Magn Magn Mater 149:67–71

    Article  CAS  Google Scholar 

  • Perez JM, O’Loughin T, Simeone FJ, Weissleder R, Josephson L (2002) DNA-based magnetic nano particle assembly acts as a magnetic relaxation nanoswitch allowing screening of dna-cleaving agents. J Am Chem Soc 124(12):2856–2857. doi:10.1021/ja017773n

    Article  CAS  Google Scholar 

  • Perrier T, Saulnier P, Benoît J-P (2010) Methods for the functionalisation of nanoparticles: new insights and perspectives. Chem A Eur J 16(38):11516–11529. doi:10.1002/chem.201000808

    Article  CAS  Google Scholar 

  • Reddy GR, Bhojani MS, McConville P, Moody J, Moffat BA, Hall DE, Kim G, Koo Y-EL, Woolliscroft MJ, Sugai JV, Johnson TD, Philbert MA, Kopelman R, Rehemtulla A, Ross BD (2006) Vascular targeted nanoparticles for imaging and treatment of brain tumors. Clin Cancer Res 12(22):6677–6686. doi:10.1158/1078-0432.ccr-06-0946

    Article  CAS  Google Scholar 

  • Skarpos H, Osipov SN, Vorob’eva DV, Odinets IL, Lork E, Roschenthaler G-V (2007) Synthesis of functionalized bisphosphonates via click chemistry. Org Biomol Chem 5(15):2361–2367

    Article  CAS  Google Scholar 

  • Sommer WJ, Weck M (2007) Facile functionalization of gold nanoparticles via microwave-assisted 1,3 dipolar cycloaddition. Langmuir 23(24):11991–11995. doi:10.1021/la7018742

    Article  CAS  Google Scholar 

  • Thielbeer F, Donaldson K, Bradley M (2011) Zeta potential mediated reaction monitoring on nano and micro particles. Bioconj Chem 22(2):144–150. doi:10.1021/bc1005015

    Article  CAS  Google Scholar 

  • Toulemon D, Pichon BP, Cattoen X, Man MWC, Begin-Colin S (2011) 2D assembly of non-interacting magnetic iron oxide nanoparticles via “click” chemistry. Chem Commun 47(43):11954–11956

    Article  CAS  Google Scholar 

  • Uhlig N, Li C-J (2011) Alkynes as an eco-compatible “on-call” functionality orthogonal to biological conditions in water. Chem Sci 2(7):1241–1249

    Article  CAS  Google Scholar 

  • White MA, Johnson JA, Koberstein JT, Turro NJ (2006) Toward the syntheses of universal ligands for metal oxide surfaces: controlling surface functionality through click chemistry. J Am Chem Soc 128(35):11356–11357. doi:10.1021/ja064041s

    Article  CAS  Google Scholar 

  • Willis AL, Turro NJ, O’Brien S (2005) Spectroscopic characterization of the surface of iron oxide nanocrystals. Chem Mater 17(24):5970–5975. doi:10.1021/cm051370v

    Article  CAS  Google Scholar 

  • Xue X, Wang F, Liu X (2011) Emerging functional nano materials for therapeutics. J Mater Chem 21(35):13107–13127

    Article  CAS  Google Scholar 

  • Zhang W, Zhang Y, Shi X, Liang C, Xian Y (2011) Rhodamine-B decorated super paramagnetic iron oxide nanoparticles: preparation, characterization and their optical/magnetic properties. J Mater Chem 21(40):16177–16183

    Article  CAS  Google Scholar 

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Acknowledgments

The authors thank the Magnisense Corporation for providing a MIAplex Reader. The authors also thank N. Lièvre (UFR SMBH, Université Paris 13, Bobigny, France) for TEM images and I. Milosevic (UMR 7244 CNRS, Université Paris 13, Bobigny, France) for her assistance concerning XRD.

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Correspondence to Erwann Guénin.

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Guénin, E., Hardouin, J., Lalatonne, Y. et al. Bivalent alkyne-bisphosphonate as clickable and solid anchor to elaborate multifunctional iron oxide nanoparticles with microwave enhancement. J Nanopart Res 14, 965 (2012). https://doi.org/10.1007/s11051-012-0965-7

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