Abstract
The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. The influence of the ionic strength on the supramolecular polymerization was probed via circular dichroism spectroscopy and cryogenic transmission electron microscopy. Physiological salt concentrations efficiently screen the charges of the dendritic building block equipped with eight sulfate groups and trigger the formation of rigid supramolecular polymers. Since multivalent sulfated supramolecular structures mimic naturally occurring L-selectin ligands, the corresponding affinity was evaluated using a competitive SPR binding assay and benchmarked to an ethylene glycol-decorated supramolecular polymer.
Highlights
Deciphering the interaction of artificial molecular building blocks with biological components is a key element on the way to understanding and selectively manipulating biological systems
After deprotection of the N-terminus with TFA, molecule 4 was suitable for coupling to the branching unit to obtain the desired dendritic peptide amphiphiles
The densely sulfated dendritic polyglycerol of similar molecular weight is able to bind in the low nanomolar range suggesting that a high density of functional groups is a key parameter [26]. These results show that the multivalent presentation of sulfate moieties on the surface of one-dimensional anisotropic supramolecular polymers noticeably enhances their affinity towards surface immobilized L-selectin
Summary
Deciphering the interaction of artificial molecular building blocks with biological components is a key element on the way to understanding and selectively manipulating biological systems. The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. Physiological salt concentrations efficiently screen the charges of the dendritic building block equipped with eight sulfate groups and trigger the formation of rigid supramolecular polymers.
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