Glycoconjugated Amphiphilic Polymers via Click-Chemistry for the Encapsulation of Quantum Dots

Herein, we present a strategy for the glycoconjugation of nanoparticles (NPs), with a special focus on fluorescent quantum dots (QDs), recently described by us as “preassembly” approach. Therein, prior to the encapsulation of diverse nanoparticles by an amphiphilic poly(isoprene)-b-poly(ethylene gly...

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Bibliographic Details
Published in:Langmuir 2013-10, Vol.29 (40), p.12593-12600
Main Authors: Schmidtke, Christian, Kreuziger, Anna-Marlena, Alpers, Dirk, Jacobsen, Anna, Leshch, Yevgeniy, Eggers, Robin, Kloust, Hauke, Tran, Huong, Ostermann, Johannes, Schotten, Theo, Thiem, Joachim, Thimm, Julian, Weller, Horst
Format: Article
Language:English
Subjects:
Cell Line, Tumor
Chemistry
Click Chemistry
Colloidal state and disperse state
Concanavalin A - chemistry
Exact sciences and technology
General and physical chemistry
Humans
Magnetic Resonance Spectroscopy
Nanoparticles - chemistry
Physical and chemical studies. Granulometry. Electrokinetic phenomena
Polymers - chemistry
Quantum Dots - chemistry
Surface Plasmon Resonance
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Summary:Herein, we present a strategy for the glycoconjugation of nanoparticles (NPs), with a special focus on fluorescent quantum dots (QDs), recently described by us as “preassembly” approach. Therein, prior to the encapsulation of diverse nanoparticles by an amphiphilic poly(isoprene)-b-poly(ethylene glycol) diblock copolymer (PI-b-PEG), the terminal PEG appendage was modified by covalently attaching a carbohydrate moiety using Huisgen-type click-chemistry. Successful functionalization was proven by NMR spectroscopy. The terminally glycoconjugated polymers were subsequently used for the encapsulation of QDs in a phase transfer process, which fully preserved fluorescence properties. Binding of these nanoconstructs to the lectin Concanavalin A (Con A) was studied via surface plasmon resonance (SPR). Depending on the carbohydrate moiety, namely, d-manno-heptulose, d-glucose, d-galactose, 2-deoxy-2-{[methylamino)carbonyl]amino}-d-glucopyranose (“des(nitroso)-streptozotocin”), or d-maltose, the glycoconjugated QDs showed enhanced affinity constants due to multivalent binding effects. None of the constructs showed toxicity from 0.001 to 1 μM (particle concentration) using standard WST and LDH assays on A549 cells.
ISSN:0743-7463
1520-5827
DOI:10.1021/la402826f