Abstract
The methyl ester of 8-oxo-8H-indeno[2′,1′:7,8]naphtho[1,2-b]thiophene-2-carboxylic acid (1) and its corresponding PEGylated ester were synthesised and fully characterised. X-ray diffraction studies on (1) confirmed the helical structure of the receptor and that it is self-assembled into layers by π–π interactions. An in-depth study by DFT calculations and MS experiments (ESI-MS, MS/MS, IMRPD and ESI-IMS-MS) was carried out between (1) and the physiological cation K+. The formation of supramolecular complexes between (1) and K+ with different stoichiometries was demonstrated and the cation K+ preferentially interacts with the oxygen atoms of the carbonyl bond of the ketone and ester groups and the sulphur atom of the heterocycle. The ability of the two synthesized aromatic architectures to transport ions across a model lipid membrane has been studied by electrophysiology experiments. The formation of pores was observed, even at nanomolar concentrations. Since the PEGylated molecule showed more regular pore definitions than the hydrophobic molecule, the introduction of a polar hydrophilic chain made it possible to control the orientation of the aromatic architectures within the membrane.
Highlights
Transport of ions across cell membranes is a crucial biological process the misregulation of which causes severe diseases currently known as channelopathies.[1]
Bearing in mind the evaluation of receptor 1 transport ability across membranes, we examined the hydrophilic/ hydrophobic balance by modifying the ester residue
We envisioned the installation of a polyethylene glycol (PEG) chain instead of the starting methyl group
Summary
Transport of ions across cell membranes is a crucial biological process the misregulation of which causes severe diseases currently known as channelopathies.[1]. One way to gain information is the development of new arti cial molecular models mimicking biological functions involved in ion transport.[2] In general, synthetic architectures able to act as ion carriers can be split into two main families: preformed cyclic scaffolds and self-assembling in the lipidic bilayer.[3] In both cases, ion transportation is mediated and aromatic systems appear crucial in biological systems,[4,10,11] contributing to the stabilization of particular conformations of proteins or the preservation of the charge balance during enzymatic catalytic processes[12,13] for example In this context, cation–p interactions with planar fused polyaromatic systems[14,15,16] or polyaromatic macrocycles, such as calixarenes[17,18] and pillar[n]arenes,[19,20,21] and more exible para-oligophenylenes,[22,23,24] have been theoretically and experimentally studied
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