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

Langmuir. 2013 Oct 8;29(40):12593-600. doi: 10.1021/la402826f. Epub 2013 Sep 26.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Click Chemistry
  • Concanavalin A / chemistry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Nanoparticles / chemistry
  • Polymers / chemistry*
  • Quantum Dots / chemistry*
  • Surface Plasmon Resonance

Substances

  • Polymers
  • Concanavalin A