One-step ligand exchange reaction as an efficient way for functionalization of magnetic nanoparticles

Journal of Nanoparticle Research

Volumn 14, Issue 7, 2012, Pages

  Mrówczyński, Radosław ^a,b   Rednic, Lidia ^b   Turcu, Rodica ^b   Liebscher, Jürgen ^a,b  

^a HUMBOLDT UNIVERSITY   (Germany)

^b NATIONAL INSTITUTE FOR RESEARCH AND DEVELOPMENT OF ISOTOPIC AND MOLECULAR TECHNOLOGIES   (Romania)

Author keywords

Click chemistry; Fatty acid; Ligand exchange; Magnetic nanoparticles

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; FATTY ACIDS; HYDROCARBONS; IRON OXIDES; LIGANDS; MAGNETISM; MAGNETITE; MEDICAL NANOTECHNOLOGY; SOLS; SYNTHESIS (CHEMICAL);

AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; COLLOIDAL STABILITY; FE3O4 NANOPARTICLES; FUNCTIONALIZATIONS; LIGAND EXCHANGE REACTIONS; LIGAND EXCHANGES; SUPERPARAMAGNETIC BEHAVIOR;

MAGNETIC NANOPARTICLES;

BIOTIN; FATTY ACID; GALACTOSE; MAGNETIC NANOPARTICLE; PROLINE; QUININE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; LIGAND EXCHANGE REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84865723401     PISSN: 13880764     EISSN: 1572896X     Source Type: Journal    
DOI: 10.1007/s11051-012-0985-3     Document Type: Article

References (47)

1. WH Binder H Weinstabl R Sachsenhofer 2008 Superparamagnetic iron oxide nanoparticles via ligand exchange reactions: organic 1,2-diols as versatile building blocks for surface engineering J Nanomater 10.1155/2008/383020
2. G Chouhan D Wang H Alper 2007 Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles Chem Commun (Camb) 45 4809 4811 10.1039/b711298j 10.1039/b711298j (Pubitemid 350119783)
3. R De Palma S Peeters MJ Van Bael H Van den Rul K Bonroy W Laureyn J Mullens G Borghs G Maes 2007 Silane ligand exchange to make hydrophobic superparamagnetic nanoparticles water-dispersible Chem Mater 19 7 1821 1831 10.1021/cm0628000 10.1021/cm0628000 (Pubitemid 46608222)
4. D Font C Jimeno MA Pericàs 2006 Polystyrene-supported hydroxyproline: an insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water Org Lett 8 20 4653 4655 10.1021/ol061964j 10.1021/ol061964j 1:CAS:528:DC%2BD28Xoslaktbk%3D (Pubitemid 44578700)
5. J Gao H Gu B Xu 2009 Multifunctional magnetic nanoparticles: design, synthesis, and biomedical applications Acc Chem Res 42 8 1097 1107 10.1021/ar9000026 10.1021/ar9000026 1:CAS:528:DC%2BD1MXmsVOmtb8%3D
6. MJ Gaunt CCC Johansson A McNally NT Vo 2007 Enantioselective organocatalysis Drug Discov Today 12 1-2 8 27 10.1016/j.drudis.2006.11.004 10.1016/j.drudis.2006.11.004 1:CAS:528:DC%2BD2sXhsFOjtg%3D%3D (Pubitemid 46014482)
7. Gleeson O, Davies GL, Peschiulli A, Tekoriute R, Gun'ko YK, Connon SJ (2011) The immobilisation of chiral organocatalysts on magnetic nanoparticles: the support particle cannot always be considered inert. Org Biomol Chem 9(22):7929-7940. doi: 10.1039/c1ob06110k
8. (4) nanoparticles Macromol Rapid Commun 31 18 1608 1615 10.1002/marc.201000193 10.1002/marc.201000193 1:CAS:528: DC%2BC3cXhtFKlsr%2FL
9. H Gotoh H Ishikawa Y Hayashi 2007 Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with alpha, beta-unsaturated aldehydes Org Lett 9 25 5307 5309 10.1021/Ol702545z 10.1021/ol702545z 1:CAS:528:DC%2BD2sXht12gs7fP
10. R Hao R Xing Z Xu Y Hou S Gao S Sun 2010 Synthesis, functionalization, and biomedical applications of multifunctional magnetic nanoparticles Adv Mater 22 25 2729 2742 10.1002/adma.201000260 10.1002/adma.201000260 1:CAS:528:DC%2BC3cXovVCkt74%3D
11. K Hayashi M Moriya W Sakamoto T Yogo 2009 Chemoselective synthesis of folic acid-functionalized magnetite nanoparticles via click chemistry for magnetic hyperthermia Chem Mater 21 7 1318 1325 10.1021/cm803113e 10.1021/cm803113e 1:CAS:528:DC%2BD1MXivF2quro%3D
12. KM Kacprzak W Lindner NM Maier 2008 An improved synthesis of 10,11-didehydro Cinchona alkaloids Chirality 20 3-4 441 445 10.1002/chir.20461 10.1002/chir.20461 1:CAS:528:DC%2BD1cXis12hurY%3D (Pubitemid 351303985)
13. Y Lalatonne C Paris JM Serfaty P Weinmann M Lecouvey L Motte 2008 Bis-phosphonates-ultra small superparamagnetic iron oxide nanoparticles: a platform towards diagnosis and therapy Chem Commun 22 2553 2555 10.1039/b801911h (Pubitemid 351748141)
14. M Lattuada TA Hatton 2007 Functionalization of monodisperse magnetic nanoparticles Langmuir 23 4 2158 2168 10.1021/La062092x 10.1021/la062092x 1:CAS:528:DC%2BD28XhtlKjsrbI (Pubitemid 46406176)
15. N Li WH Binder 2011 Click-chemistry for nanoparticle-modification J Mater Chem 21 42 16717 16734 10.1039/c1jm11558h 1:CAS:528:DC%2BC3MXhtlaqt7fL
16. X-m Li B Wang J-m Zhang M Yan 2010 Asymmetric organocatalytic double-conjugate addition of malononitrile to dienones: efficient synthesis of optically active cyclohexanones Org Lett 13 3 374 377 10.1021/ol102570b 10.1021/ol102570b
17. CW Lim IS Lee 2010 Magnetically recyclable nanocatalyst systems for the organic reactions Nano Today 5 5 412 434 10.1016/j.nantod.2010.08.008 1:CAS:528:DC%2BC3cXhs1WrtrnF
18. PC Lin SH Ueng SC Yu MD Jan AK Adak CC Yu CC Lin 2007 Surface modification of magnetic nanoparticle via Cu(I)-catalyzed alkyne-azide [2 + 3] cycloaddition Org Lett 9 11 2131 2134 10.1021/Ol070588f 10.1021/ol070588f 1:CAS:528:DC%2BD2sXkvVyls70%3D
19. HS Mader M Link DE Achatz K Uhlmann X Li OS Wolfbeis 2010 Surface-modified upconverting microparticles and nanoparticles for use in click chemistries Chem Eur J 16 18 5416 5424 10.1002/chem.201000117 1:CAS:528:DC%2BC3cXlvVWrtbs%3D
20. HB Mereyala SR Gurrala 1998 A highly diastereoselective, practical synthesis of allyl, propargyl 2,3,4,6-tetra-O-acetyl-β-d-gluco, β-d-galactopyranosides and allyl, propargyl heptaacetyl-β-d-lactosides Carbohydr Res 307 3-4 351 354 10.1016/S0008-6215(97)10104-5 1:CAS:528:DyaK1cXksVWmtL8%3D (Pubitemid 28294190)
21. F Michalek A Lagunas C Jimeno MA Pericas 2008 Synthesis of functional cobalt nanoparticles for catalytic applications. Use in asymmetric transfer hydrogenation of ketones J Mater Chem 18 39 4692 4697 10.1039/b808383e 1:CAS:528:DC%2BD1cXhtFyhur3L
22. L Peng L-L Wang J-F Bai L-N Jia Q-C Yang Q-C Huang X-Y Xu L-X Wang 2011 Highly effective and enantioselective phospho-aldol reaction of diphenyl phosphite with N-alkylated isatins catalyzed by quinine Tetrahedron Lett 52 11 1157 1160 10.1016/j.tetlet.2010.12.101 1:CAS:528:DC%2BC3MXhvFelu78%3D
23. L Polito D Monti E Caneva E Delnevo G Russo D Prosperi 2008 One-step bioengineering of magnetic nanoparticles via a surface diazo transfer/azide-alkyne click reaction sequence Chem Commun 5 621 623 10.1039/B716113a 10.1039/b716113a
24. V Polshettiwar RS Varma 2010 Nano-organocatalyst: magnetically retrievable ferrite-anchored glutathione for microwave-assisted Paal-Knorr reaction, aza-Michael addition, and pyrazole synthesis Tetrahedron 66 5 1091 1097 10.1016/j.tet.2009.11.015 1:CAS:528:DC%2BC3cXjtVGgtQ%3D%3D
25. V Polshettiwar B Baruwati RS Varma 2009 Magnetic nanoparticle-supported glutathione: a conceptually sustainable organocatalyst Chem Commun 14 1837 1839 10.1039/b900784a
26. KVS Ranganath F Glorius 2011 Superparamagnetic nanoparticles for asymmetric catalysis-a perfect match Catal Sci Technol 1 1 13 22 10.1039/c0cy00069h 1:CAS:528:DC%2BC3MXjslCitLY%3D
27. 4 magnetic nanoparticles for organocatalytic Michael reactions J Mater Chem 21 20 7350 7355 10.1039/c1jm10535c 1:CAS:528: DC%2BC3MXlsV2nsrg%3D
28. S Roy MA Pericas 2009 Functionalized nanoparticles as catalysts for enantioselective processes Org Biomol Chem 7 13 2669 2677 10.1039/b903921j 1:CAS:528:DC%2BD1MXntlOjsbo%3D
29. M Rueping CMR Volla M Bolte G Raabe 2011 General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-Pictet- Spengler or 1,2-amine addition reaction Adv Synth Catal 353 14-15 2853 2859 10.1002/adsc.201100258 10.1002/adsc.201100258 1:CAS:528:DC%2BC3MXht12qtrjK
30. B Samanta D Patra C Subramani Y Ofir G Yesilbag A Sanyal VM Rotello 2009 Stable magnetic colloidosomes via click-mediated crosslinking of nanoparticles at water-oil interfaces Small 5 6 685 688 10.1002/smll.200801659 10.1002/smll.200801659 1:CAS:528:DC%2BD1MXktlShtrc%3D
31. W Schartl 2010 Current directions in core-shell nanoparticle design Nanoscale 2 6 829 843 10.1039/c0nr00028k 1:CAS:528:DC%2BC3cXhtlKru7jK
32. TD Schladt K Schneider H Schild W Tremel 2011 Synthesis and bio-functionalization of magnetic nanoparticles for medical diagnosis and treatment Dalton Trans 40 24 6315 6343 10.1039/c0dt00689k 1:CAS:528: DC%2BC3MXntFGiu7Y%3D
33. S Shylesh V Schunemann WR Thiel 2010 Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis Angew Chem Int Ed 49 20 3428 3459 10.1002/anie.200905684 10.1002/anie.200905684 1:CAS:528:DC%2BC3cXlsFCnt78%3D
34. JA Sikorski B Devadas ME Zupec SK Freeman DL Brown H-F Lu S Nagarajan PP Mehta AC Wade NS Kishore ML Bryant DP Getman CA McWherter JI Gordon 1997 Selective peptidic and peptidomimetic inhibitors of Candida albicans myristoylCoA: protein N-myristoyltransferase: a new approach to antifungal therapy J Pept Sci 43 1 43 71 10.1002/(sici)1097-0282(1997)43:1<43::aid- bip5>3.0.co;2-0 10.1002/(SICI)1097-0282(1997)43:1<43::AID-BIP5>3.0. CO;2-0 1:CAS:528:DyaK2sXjsVyisL4%3D (Pubitemid 127570810)
35. N Tran TJ Webster 2010 Magnetic nanoparticles: biomedical applications and challenges J Mater Chem 20 40 8760 8767 10.1039/c0jm00994f 1:CAS:528:DC%2BC3cXht1Clsb%2FO
36. R Turcu O Pana A Nan I Craciunescu O Chauvet C Payen 2008 Polypyrrole coated magnetite nanoparticles from water based nanofluids J Phys D 41 24 245002 10.1088/0022-3727/41/24/245002
37. L Vékás D Bica MV Avdeev 2007 Magnetic nanoparticles and concentrated magnetic nanofluids: synthesis, properties and some applications China Particuology 5 1-2 43 49 10.1016/j.cpart.2007.01.015 (Pubitemid 46962442)
38. BG Wang BC Ma Q Wang W Wang 2010 Superparamagnetic nanoparticle-supported (S)-diphenyl-prolinol trimethylsilyl ether as a recyclable catalyst for asymmetric Michael addition in water Adv Synth Catal 352 17 2923 2928 10.1002/adsc.201000508 10.1002/adsc.201000508 1:CAS:528:DC%2BC3cXhsVCjsLjO
39. K Welser MDA Perera JW Aylott WC Chan 2009 A facile method to clickable sensing polymeric nanoparticles Chem Commun 43 6601 6603 10.1039/b914358k
40. 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)
41. X Wu X He L Zhong S Lin D Wang X Zhu D Yan 2011 Water-soluble dendritic-linear triblock copolymer-modified magnetic nanoparticles: preparation, characterization and drug release properties J Mater Chem 21 35 13611 13620 10.1039/c1jm11613d 1:CAS:528:DC%2BC3MXhtVKhtbjE
42. 4 magnetic nanoparticles for the synthesis of oligopeptides in organic solvents Chem Asian J 5 6 1389 1394 10.1002/asia.200900696 1:CAS:528:DC%2BC3cXmvFSrsbk%3D
43. C Xu K Xu H Gu R Zheng H Liu X Zhang Z Guo B Xu 2004 Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles J Am Chem Soc 126 32 9938 9939 10.1021/ja0464802 10.1021/ja0464802 1:CAS:528:DC%2BD2cXlvFGju7g%3D (Pubitemid 39079411)
44. H-M Yang CW Park S Lim S-I Park BH Chung J-D Kim 2011 Cross-linked magnetic nanoparticles from poly(ethylene glycol) and dodecyl grafted poly(succinimide) as magnetic resonance probes Chem Commun 47 46 12518 12520 10.1039/c1cc16191a 1:CAS:528:DC%2BC3MXhsVGrs7bO
45. TR Zhang JP Ge YP Hu YD Yin 2007 General approach for transferring hydrophobic nanocrystals into water Nano Lett 7 10 3203 3207 10.1021/nl071928t 1:CAS:528:DC%2BD2sXhtVarsrfK (Pubitemid 350132954)
46. (4) nanoparticles. Nanotechnology 19(17). Artn 175601. doi: 10.1088/0957-4484/19/17/175601 (Pubitemid 351588217)
47. R Zhu W Jiang Y Pu K Luo Y Wu B He Z Gu 2011 Functionalization of magnetic nanoparticles with peptide dendrimers J Mater Chem 21 14 5464 5474 10.1039/c0jm02752a 1:CAS:528:DC%2BC3MXjsFymsrk%3D