Nanostructuring of CyPLOS (Cyclic Phosphate-Linked OligoSaccharides), novel saccharide-based synthetic ion transporters

Ionophores are an important class of synthetic molecules which mimic natural ion channels or carriers. Here we report the aggregation behavior in pseudo-physiological environment of three Cyclic Phosphate-Linked Oligosaccharides (CyPLOS) derivatives, synthetic ion transporters based on cyclic, phosphate-linked disaccharide skeleton differing for the nature of the tails (tetraethylene–TEG glycol and/or n-undecyl chains) attached to the C-2 and C-3 of the constitutive monosaccharides. Their aggregation behavior has been studied by a combined use of dynamic light scattering (DLS), electron paramagnetic resonance spectroscopy (EPR) and Small Angle Neutron Scattering (SANS). DLS measurements were performed to reveal the formation and size distribution of the CyPLOS aggregates. EPR measurements, by using 5-doxyl stearic acid (5-DSA) as spin-probe, showed that the aggregates are mainly due to the formation of double layers and allowed to analyze the local fluidity. Finally, SANS measurements allowed estimating the layer thickness of the double layers. Our results indicate that the three CyPLOS analogs show self-aggregation properties that depend on the different nature of the inserted tails.

Jellyfish-shaped ionophores CyPLOS self aggregate in pseudo-physiological conditions forming large nanostructures whose morphology depends on the nature of the grafted tentacles.Figure optionsDownload high-quality image (68 K)Download as PowerPoint slideResearch highlights
► In the present study we have characterized the self assembling of amphiphilic ionophores in pseudo-physiological condition.
► Amphiphilic ionophores can lodge in biological membrane to act as ion channels or carrier.
► The amphiphilic ionophores assemble as vesicles with disordered bilayer in pseudophysiological condition.
► Vesicles structure depends on the nature of the tails attached to cyclic oligosaccharides.