Multivalent interaction and selectivities in selectin binding of functionalized gold colloids decorated with carbohydrate mimetics

Meike Roskamp, Sven Enders, Fabian Pfrengle, Shahla Yekta, Vjekoslav Dekaris, Jens Dernedde, Hans-Ulrich Reissig, Sabine Schlecht
2011 Organic and biomolecular chemistry  
Colloidal gold particles with functionalized organic shells were applied as novel selectin binders. The ligand shell was terminated with different monocyclic carbohydrate mimetics as simplified analogs of the sLe x unit found in biological selectin ligands. The multivalent presentation of the sulfated selectin binding epitopes on the gold particles led to extremely high binding affinities towards L-and P-selectin and IC 50 values in the subnanomolar range. Depending on the ring size of the
more » ... ted carbohydrate mimetic, its substitution pattern and its configuration, different selectivities for either L-selectin or P-selectin were obtained. These selectivities were not found for gold particles with simple acyclic sulfated alcohols, diols and triols in the ligand shell. In addition, the influence of the particle size and the thickness of the hydrophobic organic shell were systematically investigated.
doi:10.1039/c1ob05583f pmid:21904758 fatcat:qnd3n6zs6rbvxgvwzmraqn3ipm