The functionalization of gold nanoparticles with carbohydrate carrying thiolated ligands leads to so-called glyco-gold nanoparticles (glyco-AuNPs). Such glyco-AuNPs are promising candidates for their use in biosensing or as inhibitors of carbohydrate recognizing receptors.<br/>Here, we report the use of solid phase polymer synthesis to obtain precision glycomacromolecules that allow for the functionalization of AuNPs and give access to a variety of glyco-AuNPs with tunable features. Synthesis of the glycomacromolecules is based on the stepwise assembly of tailor-made building blocks on solid support giving monodisperse, sequence-defined oligo(amidoamines) with pendant glycoligands. Thereby, the chemical structure of the glycomacromolecules can be varied systematically changing e.g. spacing characteristics, valency and overall length of the glycomacromolecule. By the use of L-cysteine as final building block, thiolated precision glycomacromolecules were generated and successfully employed for AuNP functionalization by ligand exchange reaction.<br/>The synthesized glyco-AuNPs exhibit a high degree of functionalization and high stability in buffers of high ionic strength. Applying UV-Vis, DLS and SPR measurements, the binding behavior of differently functionalized glyco-AuNPs to model lectin Concanavalin A was investigated.<br/>Results showed that not only an increase in lectin binding can be achieved by the multivalent presentation on the AuNP surface in comparison to the free ligand but also that binding strength depends on the chemical structure of the ligand such as valency and hydrophobicity. Overall, we demonstrate the modular synthesis of glyco-AuNPs with tunable lectin binding behavior.

Enhancing and tuning the lectin binding behavior by functionalization of gold nanoparticles with precision glycomacromolecules

256th National Meeting (2018)

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