The design, synthesis and transmembrane transport studies of a biomimetic sterol-based ion channel

Pechulis, Anthony D.; Thompson, Richele J.; Fojtik, John P.; Schwartz, Herbert M.; Lisek, Carol A.; Frye, Leah L.

doi:10.1016/s0968-0896(97)00085-0

Cited by 19 publications

(15 citation statements)

References 32 publications

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“…33,36,65,66 Bis(cholic acid) derivatives have also been found to form transmembrane ion channels able to cross a membrane as a single molecule, but likely form a bundle to act as a channel. 67 Crown-ether based compounds can be synthesized as "chundles" [68][69][70][71][72] or hydraphiles 73 to act as channels. With the exception of SCMTR-like compounds, which is predicted to act only on one surface, ion-channel formers act individually or as aggregates to form complexes that cross a bilayer, thus creating a stable pore through the membrane.…”

Section: Other Anion Active Compoundsmentioning

confidence: 99%

The water-channel forming ability of heptapeptide-based anion channels: insights from molecular dynamics simulations

2013

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Section: Other Anion Active Compoundsmentioning

confidence: 99%

The water-channel forming ability of heptapeptide-based anion channels: insights from molecular dynamics simulations

2013

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“…The ester, being less flexible than the ether link, permitted some ion passage because the steroid could not contact the dodecylene unit as effectively. It is interesting to note that a channel designed with steroid walls around a central macrocycle showed extremely slow ion transport [57].…”

Section: Assessing Functionalitymentioning

confidence: 99%

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

Gokel

Daschbach

2008

Coordination Chemistry Reviews

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Hydraphiles are synthetic ionophores that were designed to mimic some properties of protein channels that conduct such cations as sodium. They use macrocyclic (crown) polyethers as amphiphilic headgroups and as entry and exit portals. Their overall length is controlled by covalent links between the two headgroups (distal macrocycles) and the "central relay" unit, typically also an azacrown. The hydraphiles insert in the bilayer membranes of synthetic phospholipid vesicles or vital cells and mediate the transport of cations. The hydraphiles were intended to be models but they are functional channels. Because they are symmetric, they are non-rectifying but they show open-close behavior characteristic of natural channels. Because they are non-rectifying, when they insert into a microbial membrane, they lead to a rapid change in osmotic balance that proves fatal to bacteria.

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“…[33], Nolte's polymerized isonitriles [34], Voyer's crown substituted peptides [13], the redox-switchable systems of Hall et al [35], and the steroid-substituted crowns of Pechulis et al [36].…”

Section: Introductionmentioning

confidence: 99%

Transport properties of solid state crown ether channel systems

Fromm

Bergougnant

2007

Solid State Sciences

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Abstract]I 3 1 were shown to possess ideally stacked crown ether molecules which form channels running in one direction through the solid state structure. By immersion of single crystals of 1 into NaOH, ion exchange takes place to yield the compound [(Na)3(DB18C6)(m 2 -H 2 O) 2/2 ][(Na)3(DB18C6)(m 2 -OH) 2/2 ]I 3 2, with slightly but significantly different cell parameters. Both compounds were tested for transport properties through these channels by using two different devices, one for water transport, the other for NaOH transport, through single crystals of 1 and 2, respectively. The results indicate that transport can take place via a hopping mechanism.

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The design, synthesis and transmembrane transport studies of a biomimetic sterol-based ion channel

Cited by 19 publications

References 32 publications

The water-channel forming ability of heptapeptide-based anion channels: insights from molecular dynamics simulations

The water-channel forming ability of heptapeptide-based anion channels: insights from molecular dynamics simulations

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

Transport properties of solid state crown ether channel systems

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