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

Journal of Nanoparticle Research

Volumn 14, Issue 7, 2012, Pages

  Guénin, Erwann ^a   Hardouin, Julie ^b   Lalatonne, Yoann ^a   Motte, Laurence ^a  

^a UNIVERSITÉ PARIS 13   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Click chemistry; Huisgen 1,3 cycloaddition; Iron oxide nanoparticle; Microwave; Nanoparticle functionalization

Indexed keywords

GRAFTING (CHEMICAL); HEMATITE; HYDROCARBONS; METAL NANOPARTICLES; MICROWAVE IRRADIATION; MICROWAVES; SCAFFOLDS; SYNTHESIS (CHEMICAL);

BIFUNCTIONAL MOLECULES; CLICK CHEMISTRY; FUNCTIONALIZATIONS; HUISGEN 1,3-CYCLOADDITION; IRON OXIDE NANOPARTICLE; MICROWAVE ENHANCEMENT; NANOPARTICLE FUNCTIONALIZATION; SUPERPARAMAGNETIC NANOPARTICLES;

MAGNETIC NANOPARTICLES;

(1 HYDROXY 1 PHOSPHONOPENT 4 YNYL)PHOSPHONIC ACID; ALKYNE; PHOSPHONIC ACID DERIVATIVE; SUPERPARAMAGNETIC IRON OXIDE NANOPARTICLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CLICK CHEMISTRY; CYCLOADDITION; MICROWAVE IRRADIATION; PRIORITY JOURNAL;

EID: 84862488040     PISSN: 13880764     EISSN: 1572896X     Source Type: Journal    
DOI: 10.1007/s11051-012-0965-7     Document Type: Article

References (37)

1. WR Algar DE Prasuhn MH Stewart TL Jennings JB Blanco-Canosa PE Dawson IL Medintz 2011 The controlled display of biomolecules on nanoparticles: a challenge suited to bioorthogonal chemistry Bioconj Chem 22 5 825 858 10.1021/bc200065z 10.1021/bc200065z 1:CAS:528:DC%2BC3MXmtVCntb0%3D
2. E Amstad T Gillich I Bilecka M Textor E Reimhult 2009 Ultra stable iron oxide nanoparticle colloidal suspensions using dispersants with catechol-derived anchor groups Nano Lett 9 12 4042 4048 10.1021/nl902212q 10.1021/nl902212q 1:CAS:528:DC%2BD1MXht1OitLfJ
3. B Baruwati MN Nadagouda RS Varma 2008 Bulk synthesis of monodisperse ferrite nanoparticles at watera-'organic interfaces under conventional and microwave hydrothermal treatment and their surface functionalization J Phys Chem C 112 47 18399 18404 10.1021/jp807245g 1:CAS:528:DC%2BD1cXhtlWqurbK
4. 3 nanoparticles as potential MRI contrast agents J Colloid Interface Sci 341 2 248 254 10.1016/j.jcis.2009.09.043
5. 3@Zoledronate Int J Pharm 379 2 324 327 10.1016/j.ijpharm.2009.04.010 1:CAS:528:DC%2BD1MXhtVKjsr3K
6. F Benyettou E Guénin L Lalatonne L Motte 2011 Microwave assisted nano particle surface functionalization Nanotechnology 22 5 055102 10.1088/0957-4484/22/5/055102 1:STN:280:DC%2BC3M%2FmtFCktg%3D%3D
7. F Bertorelle C Wilhelm J Roger F Gazeau C Ménager V Cabuil 2006 Fluorescence-modified super paramagnetic nanoparticles: intracellular uptake and use in cellular imaging Langmuir 22 12 5385 5391 10.1021/la052710u 10.1021/la052710u 1:CAS:528:DC%2BD28XktlKmurs%3D (Pubitemid 43954516)
8. I Bilecka I Djerdj M Niederberger 2008 One-minute synthesis of crystalline binary and ternary metal oxide nanoparticles Chem Commun 21 7 886 888 10.1039/b717334b (Pubitemid 351208238)
9. C Bouillon A Meyer S Vidal A Jochum Y Chevolot J-P Cloarec J-P Praly J-J Vasseur F Morvan 2006 Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support J Org Chem 71 4700 4702 10.1021/jo060572n 1:CAS:528:DC%2BD28XksFKktL8%3D (Pubitemid 43849584)
10. X Chen SS Gambhir J Cheon 2011 Theranostic nanomedicine Acc Chem Res 44 10 841 1134 10.1021/ar200231d 10.1021/ar200231d 1:CAS:528:DC%2BC3MXhtlSlurfL Special issue on theranostic nanomedecine
11. SR Dave X Gao 2009 Monodisperse magnetic nanoparticles for biodetection, imaging, and drug delivery: a versatile and evolving technology Wiley Interdiscip Rev Nanomed Nanobiotechnol 1 6 583 609 10.1002/wnan.51 10.1002/wnan.51 1:CAS:528:DC%2BC3cXmtVSrurc%3D
12. B Dubertret M Calame AJ Libchaber 2001 Single-mismatch detection using gold-quenched fluorescent oligonucleotides Nat Biotechnol 19 365 370 10.1038/86762 1:CAS:528:DC%2BD3MXis1Smsbk%3D (Pubitemid 32275347)
13. E Guénin M Monteil N Bouchemal T Prangé M Lecouvey 2007 Syntheses of phosphonic esters of alendronate, pamidronate and neridronate Eur J Org Chem 20 3380 3391 10.1002/ejoc.200601067
14. JB Haun T-J Yoon H Lee R Weissleder 2010 Magnetic nano particle biosensors Wiley Interdiscip Rev Nanomed Nanobiotechnol 2 3 291 304 10.1002/wnan.84 10.1002/wnan.84 1:CAS:528:DC%2BC3cXmtlWgtLo%3D
15. A Karimi B Denizot F Hindré R Filmon J-M Greneche S Laurent T Daou S Begin-Colin J-J Le Jeune 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 10.1007/s11051-009-9815-7 10.1007/s11051-009-9815-7 1:CAS:528:DC%2BC3cXkvFehur4%3D
16. Y Lalatonne C Paris JM Serfaty P Weinmann M Lecouvey L Motte 2008 Bis-phosphonates-ultra small super paramagnetic iron oxide nanoparticles: a platform towards diagnosis and therapy Chem Commun 14 22 2553 2555 10.1039/b801911h (Pubitemid 351748141)
17. N Li WH Binder 2011 Click-chemistry for nano particle-modification J Mater Chem 21 42 16717 16734 10.1039/c1jm11558h 1:CAS:528:DC%2BC3MXhtlaqt7fL
18. SK Mandal N Lequeux B Rotenberg M Tramier J Fattaccioli J Bibette B Dubertret 2005 Encapsulation of magnetic and fluorescent nanoparticles in emulsion droplets Langmuir 21 9 4175 4179 10.1021/la047025m 10.1021/la047025m 1:CAS:528:DC%2BD2MXis1OhtLs%3D (Pubitemid 40654629)
19. A Martin J Hickey A Ablack J Lewis L Luyt E Gillies 2010 Synthesis of bombesin-functionalized iron oxide nanoparticles and their specific uptake in prostate cancer cells J Nanopart Res 12 5 1599 1608 10.1007/s11051-009-9681-3 10.1007/s11051-009-9681-3 1:CAS:528:DC%2BC3cXmsFOruro%3D
20. JR McCarthy R Weissleder 2008 Multifunctional magnetic nanoparticles for targeted imaging and therapy Adv Drug Deliv Rev 60 11 1241 1251 10.1016/j.addr.2008.03.014 1:CAS:528:DC%2BD1cXosVOnsr0%3D
21. M Meldal CW Tornoe 2008 Cu-catalyzed azide-alkyne cycloaddition Chem Rev 108 8 2952 3015 10.1021/cr0783479 10.1021/cr0783479 1:CAS:528: DC%2BD1cXps1yhurk%3D
22. E Migianu E Guénin M Lecouvey 2005 New efficient synthesis of 1-hydroxymethylene-1,1-bisphosphonic monomethyl esters Synlett 5 0425 0428
23. I Milosevic H Jouni C David F Warmont D Bonnin L Motte 2011 Facile microwave process in water for the fabrication of magnetic nano rods J Phys Chem C 115 39 18999 19004 10.1021/jp205334v 10.1021/jp205334v 1:CAS:528: DC%2BC3MXhtFOitLfF
24. L Motte F Benyettou C de Beaucorps M Lecouvey I Milesovic Y Lalatonne 2010 Multimodal super paramagnetic nanoplatform for clinical applications: immunoassays, imaging & therapy Faraday Discuss 149 211 225 10.1039/c005286h
25. N Moumen P Veillet MP Pileni 1995 Controlled preparation of nano size cobalt ferrite magnetic particles J Magn Magn Mater 149 67 71 10.1016/0304-8853(95)00340-1 1:CAS:528:DyaK2MXns1GjsbY%3D
26. JM Perez T O'Loughin FJ Simeone R Weissleder L Josephson 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 10.1021/ja017773n 10.1021/ja017773n 1:CAS:528:DC%2BD38XhsFWrtrs%3D (Pubitemid 34249946)
27. T Perrier P Saulnier J-P Benoît 2010 Methods for the functionalisation of nanoparticles: new insights and perspectives Chem A Eur J 16 38 11516 11529 10.1002/chem.201000808 10.1002/chem.201000808 1:CAS:528:DC%2BC3cXhsVSrtLbK
28. GR Reddy MS Bhojani P McConville J Moody BA Moffat DE Hall G Kim Y-EL Koo MJ Woolliscroft JV Sugai TD Johnson MA Philbert R Kopelman A Rehemtulla BD Ross 2006 Vascular targeted nanoparticles for imaging and treatment of brain tumors Clin Cancer Res 12 22 6677 6686 10.1158/1078-0432.ccr-06-0946 10.1158/1078-0432.CCR-06-0946 1:CAS:528:DC%2BD28Xht1elsL%2FP (Pubitemid 44876835)
29. H Skarpos SN Osipov DV Vorob'eva IL Odinets E Lork G-V Roschenthaler 2007 Synthesis of functionalized bisphosphonates via click chemistry Org Biomol Chem 5 15 2361 2367 10.1039/b705510b 1:CAS:528:DC%2BD2sXnsl2ns7s%3D (Pubitemid 47118870)
30. WJ Sommer M Weck 2007 Facile functionalization of gold nanoparticles via microwave-assisted 1,3 dipolar cycloaddition Langmuir 23 24 11991 11995 10.1021/la7018742 10.1021/la7018742 1:CAS:528:DC%2BD2sXhtFOitLnO (Pubitemid 350197361)
31. F Thielbeer K Donaldson M Bradley 2011 Zeta potential mediated reaction monitoring on nano and micro particles Bioconj Chem 22 2 144 150 10.1021/bc1005015 10.1021/bc1005015 1:CAS:528:DC%2BC3MXmsVWltQ%3D%3D
32. D Toulemon BP Pichon X Cattoen MWC Man S Begin-Colin 2011 2D assembly of non-interacting magnetic iron oxide nanoparticles via "click" chemistry Chem Commun 47 43 11954 11956 10.1039/c1cc14661k 1:CAS:528: DC%2BC3MXhtlKgtrnE
33. N Uhlig C-J Li 2011 Alkynes as an eco-compatible "on-call" functionality orthogonal to biological conditions in water Chem Sci 2 7 1241 1249 10.1039/c1sc00164g 1:CAS:528:DC%2BC3MXnsVyhtrY%3D
34. MA White JA Johnson JT Koberstein NJ Turro 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 10.1021/ja064041s 10.1021/ja064041s 1:CAS:528:DC%2BD28Xot1Kgs7w%3D (Pubitemid 44338820)
35. AL Willis NJ Turro S O'Brien 2005 Spectroscopic characterization of the surface of iron oxide nanocrystals Chem Mater 17 24 5970 5975 10.1021/cm051370v 10.1021/cm051370v 1:CAS:528:DC%2BD2MXhtFOhsL7M (Pubitemid 41784401)
36. X Xue F Wang X Liu 2011 Emerging functional nano materials for therapeutics J Mater Chem 21 35 13107 13127 10.1039/c1jm11401h 1:CAS:528:DC%2BC3MXhtVKhtbvL
37. W Zhang Y Zhang X Shi C Liang Y Xian 2011 Rhodamine-B decorated super paramagnetic iron oxide nanoparticles: preparation, characterization and their optical/magnetic properties J Mater Chem 21 40 16177 16183 10.1039/c1jm12353j 1:CAS:528:DC%2BC3MXht1GrtLjE