title: Glycoconjugated amphiphilic polymers via click-chemistry for the encapsulation of quantum dots.
abstract: 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.
authors.affiliation: Institute of Physical Chemistry, University of Hamburg , Grindelallee 117, 20146 Hamburg, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Schmidtke
authors.forename: Anna-Marlena
authors.initials: AM
authors.lastname: Kreuziger
authors.forename: Dirk
authors.initials: D
authors.lastname: Alpers
authors.forename: Anna
authors.initials: A
authors.lastname: Jacobsen
authors.forename: Yevgeniy
authors.initials: Y
authors.lastname: Leshch
authors.forename: Robin
authors.initials: R
authors.lastname: Eggers
authors.forename: Hauke
authors.initials: H
authors.lastname: Kloust
authors.forename: Huong
authors.initials: H
authors.lastname: Tran
authors.forename: Johannes
authors.initials: J
authors.lastname: Ostermann
authors.forename: Theo
authors.initials: T
authors.lastname: Schotten
authors.forename: Joachim
authors.initials: J
authors.lastname: Thiem
authors.forename: Julian
authors.initials: J
authors.lastname: Thimm
authors.forename: Horst
authors.initials: H
authors.lastname: Weller
mesh_terms: D045744:Cell Line, Tumor; D057930:Click Chemistry; D003208:Concanavalin A / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D053758:Nanoparticles / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D045663:Quantum Dots / Q000737:chemistry*; D020349:Surface Plasmon Resonance
chemical_list: D011108:Polymers; D003208:Concanavalin A