Modeling the Selectivity of Potassium Channels with Synthetic, Ligand-Assembled π Slides

Tedesco, Maureen M.; Ghebremariam, Bereket; Sakai, Naomi; Matile, Stefan

doi:10.1002/(sici)1521-3773(19990215)38:4<540::aid-anie540>3.0.co;2-n

Cited by 118 publications

(90 citation statements)

References 6 publications

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“…Because of the multiply coupled processes involved, cation selectivity is still detectable with proton selective transporters like 1, 2 although the observed changes upon external cation exchange are necessarily weaker compared to potassium selective channels like 2 (compare below discussion of proton selectivity). 4 Anion selectivity can be found analogously. A small change of the detected increase in HPTS emission with time upon exchange of external Cl À with Br À demonstrates that the channel transports anions with weak selectivity (Fig.…”

Section: Determination Of Anion/cation Selectivity In Vesicles For Symentioning

confidence: 99%

“…4b). 4 Without the programmed p-septiphenyl assembly with the multivalent polyhistidine ligand, the selectivity sequence of 2 degenerated to a rubidium-selective Eisenman III topology. The proton transporter 1 exhibited a less interesting, almost exclusively dehydration dominated Eisenman II sequence.…”

Section: Determination Of Selectivity Sequences In Vesiclesmentioning

confidence: 99%

“…1,4 Conceived at a time when cation-p interactions were believed to account for the selectivity of biological potassium channels, 5,6 the found Eisenman IV topology provided, ironically, excellent experimental support for a mechanism that ultimately turned out not to occur in nature (except for the blockage with the classical cation-p probe TEA þ ). The electron-deficient rigid-rod p-stack architecture of ion channel 3 was designed to open in response to chargetransfer complex formation with intercalating pdonors.…”

Section: Introductionmentioning

confidence: 99%

“…Ion selectivity in vesicles (LUVs) and planar bilayers (BLMs) of representative synthetic ion channels and pores that are constructed from rigid-rod p-oligophenyl scaffolds and contain hydrogen-bonded chains for proton transport (1), ligandassembled p-slides for potassium transport (2), p-stacks for ligand gating and electron transport (3), push-pull rods for voltage gating (4) and b-sheets for multifunctionality (molecular recognition and transformation of guests and substrates, [4][5][6]. See recent accounts 1,11 or original literature for details beyond ion selectivity…”

Section: Introductionmentioning

confidence: 99%

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The determination of the ion selectivity of synthetic ion channels and pores in vesicles

Sakai

Matile

2006

J of Physical Organic Chem

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Organic chemists entering the field of synthetic ion channels and pores are often restricted to the characterization of their creation by fluorescence kinetics in vesicles and do not have access to conductance experiments in planar bilayer membranes. This limitation excludes the application of methods to evaluate key characteristics such as ion selectivity or voltage gating that are routine in the membrane biophysics community.

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Section: Determination Of Anion/cation Selectivity In Vesicles For Symentioning

confidence: 99%

Section: Determination Of Selectivity Sequences In Vesiclesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The determination of the ion selectivity of synthetic ion channels and pores in vesicles

Sakai

Matile

2006

J of Physical Organic Chem

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“…It complements early cation-π slides, where cation-π interactions along ligand-assembled p-octiphenyl scaffolds are used to transport potassium cations across bilayer membranes [18]. Compared to the straightforward interactions of cations with conventional π-basic aromatic rings, the creation of functional systems that operate on anion-π interactions is much more demanding because it requires rigid-rod scaffolds that contain π-acidic aromatic rings.…”

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confidence: 99%

Artificial tongues and leaves

Banerji

Bhosale

Bollot

et al. 2008

Pure and Applied Chemistry

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Abstract:The objective with synthetic multifunctional nanoarchitecture is to create large suprastructures with interesting functions. For this purpose, lipid bilayer membranes or conducting surfaces have been used as platforms and rigid-rod molecules as shape-persistent scaffolds. Examples for functions obtained by this approach include pores that can act as multicomponent sensors in complex matrices or rigid-rod π-stack architecture for artificial photosynthesis and photovoltaics.Keywords: nanoarchitecture; sensors; photovoltaics; photosynthesis; lipid bilayer; scaffolds.The objective with synthetic multifunctional nanoarchitecture is to create large suprastructures with interesting functions [1,2]. To address this challenge, we often begin with lipid bilayer membranes or, more recently, conducting surfaces as platforms. To direct, control, and stabilize advanced functional architecture, rigid-rod molecules [3][4][5][6][7][8][9][10] have been introduced as shape-persistent scaffolds. Somehow the antithesis to foldamers [11,12], these simple sturdy rods are attractive scaffolds, bypassing all folding problems because they do not fold. Unknown in biology, rigid-rod molecules are much appreciated in the materials sciences [3]. Prominent members of this family of oligomeric molecules include oligoacetylene 1, p-oligophenyls 2 [4,5] and their formal mixture, i.e., p-oligophenyleneethynylene (OPE) rods 3 [6,7] (Fig. 1). Whereas the benzene rings in p-oligophenyls 2 and OPEs 3 can rotate more or less freely, oligonaphthalenes 4 cannot. This produces an exceptionally complex axial stereochemistry [8]. Rigid oligonaphthalenediimide (O-NDI) rods 5 [9] and oligoperylenediimides (O-PDI) rods 6 [10] are of interest because they are colorizable, π-acidic n-semiconductors. Oligoporphyrins are extensively studied because of their optoelectric properties, the nonplanar rod 7 has been elongated up to l = 1060 Å of the monodisperse 128-mer [11].From this rich collection of rigid-rod molecules, we originally selected p-oligophenyls 2 as model rods [1,2,14]. p-Oligophenyls are not only straightforward to synthesize and derivatize but also nonplanar and fluorescent, and can exhibit a dynamic axial chirality. The torsion angles between neighboring phenyls of the p-oligophenyl scaffold provide the directionality that is needed to control advanced supramolecular architecture. Dynamic chirality and fluorescence are of use for structural studies in

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Conformational and orientation studies of artificial ion channels incorporated into lipid bilayers

et al. 2000

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Modeling the Selectivity of Potassium Channels with Synthetic, Ligand-Assembled π Slides

Abstract: A supramolecular ion channel model mediates transmembrane ion transport (shown schematically) with a selectivity topology similar to that of K channels. This supports the biological significance of flexible arene arrays as selective cation binding sites.

Cited by 118 publications

References 6 publications

The determination of the ion selectivity of synthetic ion channels and pores in vesicles

The determination of the ion selectivity of synthetic ion channels and pores in vesicles

Artificial tongues and leaves

Conformational and orientation studies of artificial ion channels incorporated into lipid bilayers

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