Glycoconjugated amphiphilic polymers via click-chemistry for the encapsulation of quantum dots

Langmuir

Volumn 29, Issue 40, 2013, Pages 12593-12600

  Schmidtke, Christian ^a   Kreuziger, Anna Marlena ^a   Alpers, Dirk ^a   Jacobsen, Anna ^a   Leshch, Yevgeniy ^a   Eggers, Robin ^a   Kloust, Hauke ^a   Tran, Huong ^a   Ostermann, Johannes ^a   Schotten, Theo ^b   Thiem, Joachim ^a   Thimm, Julian ^a   Weller, Horst ^a,b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b Center for Applied Nanotechnology   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILIC POLYMERS; FLUORESCENCE PROPERTIES; FLUORESCENT QUANTUM DOTS; FUNCTIONALIZATIONS; MULTIVALENT BINDING; NANOPARTICLE (NPS); PARTICLE CONCENTRATIONS; PHASE TRANSFER PROCESS;

CARBOHYDRATES; FLUORESCENCE; GLUCOSE; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHYLENE OXIDES; POLYMERS; SEMICONDUCTOR QUANTUM DOTS; SURFACE PLASMON RESONANCE;

POLYETHYLENE GLYCOLS;

CONCANAVALIN A; NANOPARTICLE; POLYMER; QUANTUM DOT;

ARTICLE; CHEMISTRY; CLICK CHEMISTRY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE PLASMON RESONANCE; TUMOR CELL LINE;

CELL LINE, TUMOR; CLICK CHEMISTRY; CONCANAVALIN A; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; NANOPARTICLES; POLYMERS; QUANTUM DOTS; SURFACE PLASMON RESONANCE;

EID: 84885414381     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la402826f     Document Type: Article

References (42)

1. Varki, A. Biological Roles of Oligosaccharides: All of the Theories Are Correct Glycobiology 1993, 3, 97-130
2. Lis, H.; Sharon, N. Protein Glycosylation. Structural and Functional Aspects Eur. J. Biochem. 1993, 218, 1-27
3. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors Angew. Chem., Int. Ed. 1998, 37, 2754-2794
4. Wang, X.; Ramström, O.; Yan, M. Glyconanomaterials: Synthesis, Characterization, and Ligand Presentation Adv. Mater. 2010, 22, 1946-1953
5. Lee, Y.; Lee, R. Carbohydrate-Protein Interactions: Basis of Glycobiology Acc. Chem. Res. 1995, 28, 321-327
6. Schumacher, U. A Critical Evaluation of Neoglycoprotein Binding Sites in Vivo and in Sections of Mouse Tissues Histochemistry 1992, 97, 95-99
7. Wu, X.; Liu, H.; Liu, J.; Haley, K. N.; Treadway, J. A.; Larson, J. P.; Ge, N.; Peale, F.; Bruchez, M. P. Immunofluorescent Labeling of Cancer Marker Her2 and Other Cellular Targets with Semiconductor Quantum Dots Nat. Biotechnol. 2003, 21, 4-46
8. Burda, C.; Chen, X.; Narayanan, R.; El-Sayed, M. A. Chemistry and Properties of Nanocrystals of Different Shapes Chem. Rev. 2005, 105, 1025-1102
9. Hernáiz, M. J.; de la Fuente, J. M.; Barrientos, á. G.; Penadés, S. A Model System Mimicking Glycosphingolipid Clusters to Quantify Carbohydrate Self-Interactions by Surface Plasmon Resonance Angew. Chem., Int. Ed. 2002, 41, 1554-1557
10. Huang, H.; Yuan, Q.; Yang, X. Preparation and Characterization of Metal-Chitosan Nanocomposites Colloids Surf., B 2004, 39, 31-37
11. Moros, M.; Hernáez, B.; Garet, E.; Dias, J. T.; Sáez, B.; Grazú, V.; González-Fernández, A.; Alonso, C.; de la Fuente, J. M. Monosaccharides versus PEG-Functionalized NPs: Influence in the Cellular Uptake ACS Nano 2012, 6, 1565-1577
12. El-Boubbou, K.; Zhu, D. C.; Vasileiou, C.; Borhan, B.; Prosperi, D.; Li, W.; Huang, X. Magnetic Glyco-Nanoparticles: A Tool To Detect, Differentiate, and Unlock the Glyco-Codes of Cancer via Magnetic Resonance Imaging J. Am. Chem. Soc. 2010, 132, 4490-4499
13. Babu, P.; Sinha, S.; Surolia, A. Sugar-Quantum Dot Conjugates for a Selective and Sensitive Detection of Lectins Bioconjugate Chem. 2007, 18, 146-151
14. Kikkeri, R.; Lepenies, B.; Adibekian, A.; Laurino, P.; Seeberger, P. In Vitro Imaging and in Vivo Liver Targeting with Carbohydrate Capped Quantum Dots J. Am. Chem. Soc. 2009, 131, 2110-2112
15. Freichels, H.; Alaimo, D.; Auzély-Velty, R.; Jéroîme, C. α-Acetal, ω-Alkyne Poly(ethylene oxide) as a Versatile Building Block for the Synthesis of Glycoconjugated Graft-Copolymers Suited for Targeted Drug Delivery Bioconjugate Chem. 2012, 23, 1740-1752
16. Sunasee, R.; Narain, R. Glycopolymers and Glyco-nanoparticles in Biomolecular Recognition Processes and Vaccine Development Macromol. Biosci. 2013, 13, 9-27
17. Becer, C. R.; Gibson, M. I.; Geng, J.; Ilyas, R.; Wallis, R.; Mitchell, D. A.; Haddleton, D. M. High-Affinity Glycopolymer Binding to Human DC-SIGN and Disruption of DC-SIGN Interactions with HIV Envelope Glycoprotein J. Am. Chem. Soc. 2010, 132, 15130-15132
18. 2+-Mediated Carbohydrate-Carbohydrate Interaction Biomacromolecules 2010, 11, 13-19
19. Gou, Y.; Geng, J.; Richards, S.-J.; Burns, J.; Becer, C. R.; Haddleton, D. M. A Detailed Study on Understanding Glycopolymer Library and Con A Interactions J. Polym. Sci., Part A-1: Polym. Chem. 2013, 51, 2588-2597
20. Pellegrino, T.; Manna, L.; Kudera, S.; Liedl, T.; Koktysh, D.; Rogach, A. L.; Keller, S.; Rädler, J.; Natile, G.; Parak, W. J. Hydrophobic Nanocrystals Coated with an Amphiphilic Polymer Shell: A General Route to Water Soluble Nanocrystals Nano Lett. 2004, 4, 703-707
21. Lin, C.-A. J.; Sperling, R. A.; Li, J. K.; Yang, T.-Y.; Li, P.-Y.; Zanella, M.; Chang, W. H.; Parak, W. J. Design of an Amphiphilic Polymer for Nanoparticle Coating and Functionalization Small 2008, 4, 334-341
22. Pöselt, E.; Schmidtke, C.; Fischer, S.; Peldschus, K.; Salamon, J.; Kloust, H.; Tran, H.; Pietsch, A.; Heine, M.; Adam, G.; Schumacher, U.; Wagener, C.; Förster, S.; Weller, H. Tailor-Made Quantum Dot and Iron Oxide Based Contrast Agents for in Vitro and in Vivo Tumor Imaging ACS Nano 2012, 6, 3346-3355
23. Schmidtke, C.; Pöselt, E.; Ostermann, J.; Pietsch, A.; Kloust, H.; Tran, H.; Schotten, T.; Bastús, N. G.; Eggers, R.; Weller, H. Amphiphilic, Cross-Linkable Diblock Copolymers for Multifunctionalized Nanoparticles as Biological Probes Nanoscale 2013, 5, 7433-7444
24. Talapin, D. V.; Mekis, I.; Gotzinger, S.; Kornowski, A.; Benson, O.; Weller, H. CdSe/CdS/ZnS and CdSe/ZnSe/ZnS Core-Shell-Shell Nanocrystals J. Phys. Chem. B 2004, 108, 18826-18831
25. Yu, W. W.; Falkner, J. C.; Yavuz, C. T.; Colvin, V. L. Synthesis of Monodisperse Iron Oxide Nanocrystals by Thermal Decomposition of Iron Carboxylate Salts Chem. Commun. 2004, 20, 2306-2307
26. Bastús, N. G.; Comenge, J.; Puntes, V. Kinetically Controlled Seeded Growth Synthesis of Citrate-Stabilized Gold Nanoparticles of up to 200 nm: Size Focusing versus Ostwald Ripening Langmuir 2011, 27, 11098-11105
27. Silva, D. J.; Wang, H.; Allanson, N. M.; Jain, R. K.; Sofia, M. J. Stereospecific Solution- and Solid-Phase Glycosylations. Synthesis of β-Linked Saccharides and Construction of Disaccharide Libraries Using Phenylsulfenyl 2-Deoxy-2-Trifluoroacetamido Glycopyranosides as Glycosyl Donors J. Org. Chem. 1999, 64, 5926-5929
28. Ran, C.; Pantazopoulos, P.; Medarova, Z.; Moore, A. Synthesis and Testing of Beta-Cell-Specific Streptozotocin-Derived Near-Infrared Imaging Probes Angew. Chem., Int. Ed. 2007, 46, 8998-9001
29. Bates, R. W.; Dewey, M. R. A Formal Synthesis of Swainsonine by Gold-Catalyzed Allene Cyclization Org. Lett. 2009, 11, 3706-3708
30. Zissis, E.; Stewart, L. C.; Richtmyer, N. K. The Formation of 2,7-Anhydro- β-d-manno -heptulopyranose by the Action of Acid on d-manno -Heptulose and of Alkali on Phenyl α-d-manno -Heptulopyranoside; also 1,6-Anhydro-β- d -mannopyranose from d -Mannose in Acid Solution J. Am. Chem. Soc. 1957, 79, 2593-2597
31. Lee, J. W.; Jun, S. I.; Kim, K. An Efficient and Practical Method for the Synthesis of Mono-N-Protected α,ω-Diaminoalkanes Tetrahedron Lett. 2001, 42, 2709-2711
32. Waschke, D.; Thimm, J.; Thiem, J. Highly Efficient Synthesis of Ketoheptoses Org. Lett. 2011, 13, 3628-3631
33. Schmidtke, C.; Lange, H.; Tran, H.; Ostermann, J.; Kloust, H.; Bastús, N. G.; Merkl, J.-P.; Thomsen, C.; Weller, H. Radical Initiated Reactions on Biocompatible CdSe-Based Quantum Dots: Ligand Crosslinking, Crystal Annealing and Fluorescence Enhancement J. Phys. Chem. C 2013, 117, 8570-8578
34. Gu, F.; Zhang, L.; Teply, B. A.; Mann, N.; Wang, A.; Radovic-Moreno, A. F.; Langer, R.; Farokhzad, O. C. Precise Engineering of Targeted Nanoparticles by Using Self-Assembled Biointegrated Block Copolymers Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2586-2591
35. Huisgen, R.; Szeimies, G.; Möbius, L. 1.3-Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC-Mehrfachbindungen Chem. Ber. 1967, 100, 2494-2507
36. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
37. Webster, O. W. Living Polymerization Methods Science 1991, 251, 887-893
38. Karakoti, A. S.; Das, S.; Thevuthasan, S.; Seal, S. PEGylated Inorganic Nanoparticles Angew. Chem., Int. Ed. 2011, 50, 1980-1994
39. Bernardin, A.; Cazet, A.; Guyon, L.; Delannoy, P.; Vinet, F.; Bonnaffé, D.; Texier, I. Copper-Free Click Chemistry for Highly Luminescent Quantum Dot Conjugates: Application to in Vivo Metabolic Imaging Bioconjugate Chem. 2010, 21, 583-588
40. Weis, W. I.; Drickamer, K. Structural Basis of Lectin-Carbohydrate Recognition Annu. Rev. Biochem. 1996, 65, 441-473
41. Sigmundsson, K.; Másson, G.; Rice, R.; Beauchemin, N.; Öbrink, B. Determination of Active Concentrations and Association and Dissociation Rate Constants of Interacting Biomolecules: An Analytical Solution to the Theory for Kinetic and Mass Transport Limitations in Biosensor Technology and Its Experimental Verification Biochemistry 2002, 41, 8263-8276
42. Tassa, C.; Duffner, J. L.; Lewis, T. A.; Weissleder, R.; Schreiber, S. L.; Koehler, A. N.; Shaw, S. Y. Binding Affinity and Kinetic Analysis of Targeted Small Molecule-Modified Nanoparticles Bioconjugate Chem. 2010, 21, 14-19