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Rigid-rod anion-π slides for multiion hopping across lipid bilayers

Published in Organic and Biomolecular Chemistry. 2007, vol. 5, no. 18, p. 3000-3012
Abstract Shape-persistent oligo-p-phenylene-N,N-naphthalenediimide (O-NDI) rods are introduced as anion-pi slides for chloride-selective multiion hopping across lipid bilayers. Results from end-group engineering and covalent capture as O-NDI hairpins suggested that self-assembly into transmembrane O-NDI bundles is essential for activity. A halide topology VI (Cl > F > Br approximately I, Cl/Br approximately Cl/I > 7) implied strong anion binding along the anion-pi slides with relatively weak contributions from size exclusion (F >or= OAc). Anomalous mole fraction effects (AMFE) supported the occurrence of multiion hopping along the pi-acidic O-NDI rods. The existence of anion-pi interactions was corroborated by high-level ab initio and DFT calculations. The latter revealed positive NDI quadrupole moments far beyond the hexafluorobenzene standard. Computational studies further suggested that anion binding occurs at the confined, pi-acidic edges of the sticky NDI surface and is influenced by the nature of the phenyl spacer between two NDIs. With regard to methods development, a detailed analysis of the detection of ion selectivity with the HPTS assay including AMFE in vesicles is provided.
PMID: 17728867
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GORTEAU, Virginie et al. Rigid-rod anion-π slides for multiion hopping across lipid bilayers. In: Organic and Biomolecular Chemistry, 2007, vol. 5, n° 18, p. 3000-3012. https://archive-ouverte.unige.ch/unige:6928

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Deposited on : 2010-06-18

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