nach oben

Journal of Nanoparticle Research

Erschienen in:

01.07.2012 | Research Paper

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

verfasst von: Erwann Guénin, Julie Hardouin, Yoann Lalatonne, Laurence Motte

Erschienen in: Journal of Nanoparticle Research | Ausgabe 7/2012

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

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.

Vorheriger Artikel Temperature-dependent morphological evolution of clustered gold surface

Nächster Artikel Bioactive glass (type 45S5) nanoparticles: in vitro reactivity on nanoscale and biocompatibility

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

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 CrossRef

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 CrossRef

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

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):248–254CrossRef

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):324–327CrossRef

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

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 CrossRef

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

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 71:4700–4702CrossRef

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

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 CrossRef

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

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

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 CrossRef

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 CrossRef

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):2553–2555CrossRef

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

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 CrossRef

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 CrossRef

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

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

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

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 CrossRef

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 149:211–225CrossRef

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

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 CrossRef

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 CrossRef

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 CrossRef

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):2361–2367CrossRef

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 CrossRef

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 CrossRef

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):11954–11956CrossRef

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

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 CrossRef

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 CrossRef

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

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):16177–16183CrossRef

Titel: Bivalent alkyne-bisphosphonate as clickable and solid anchor to elaborate multifunctional iron oxide nanoparticles with microwave enhancement
verfasst von: Erwann Guénin
Julie Hardouin
Yoann Lalatonne
Laurence Motte
Publikationsdatum: 01.07.2012
Verlag: Springer Netherlands
Erschienen in: Journal of Nanoparticle Research / Ausgabe 7/2012
Print ISSN: 1388-0764
Elektronische ISSN: 1572-896X
DOI: https://doi.org/10.1007/s11051-012-0965-7

Premium Partner

Marktübersichten

Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.

Zur Marktübersicht

Springer Professional

Abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 7/2012

Microstructure, magnetic and transport properties of magnetoresistive Cu80Fe x Ni20−x (x = 5, 10 and 15 at.%) ribbons

Cisplatin and quantum dots encapsulated in liposomes as multifunctional nanocarriers for theranostic use in brain and skin

Magnetic carbon nanotubes: synthesis by a simple solvothermal process and application in magnetic targeted drug delivery system

Interaction of bilirubin with Ag and Au ions: green synthesis of bilirubin-stabilized nanoparticles

Homogeneous ZnO nanostructure arrays on GaAs substrates by two-step chemical bath synthesis

Aerogel–copper nanocomposites prepared using the adsorption of a polyfluorinated complex from supercritical CO2

Premium Partner

Marktübersichten