Self-assembly of crown ether-based amphiphiles for constructing synthetic ion channels: the relationship between structure and transport activity

Liu, Tao; Bao, Chunyan; Wang, Haiyan; Fei, Linbo; Yang, Rongyan; Long, Yi‐Tao; Zhu, Linyong

doi:10.1039/c4nj00297k

Cited by 26 publications

(26 citation statements)

References 45 publications

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“…The downfield shifted signal of the NH protons with increasing concentration in the concentrated NMR spectra indicated the formation of self-assembly through intermolecular H-bonding (Fig. 16,39,40 Channel current studies in planar lipid bilayers A patch-clamp technique in the planar membrane was first applied to characterize ion transport of the synthetic ion channels, Scheme 1 Schematic of (a) the molecular structures, (b) the proposed channel-like self-assembly of M1 and M2 in the BLMs, (c) the photolysis mechanism of M1, and (d) the proposed light-deactivated ion transport mechanism of M1 and M2. S2, ESI †).…”

Section: Resultsmentioning

confidence: 99%

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Meng

Lin

et al. 2015

New J. Chem.

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Inspired by the critical role of ion channel proteins in the regulation of cellular activities, here we developed a new type of synthetic ion channel by simple benzocrown ether-based derivatives M1and M2, where M1 had a dodecyl tail and M2 had a diethylene glycol-conjugated dodecyl tail.Being amphiphilic in nature, the two small molecules were assumed to form crown ether channels through supramolecular interactions in bilayer lipid membranes (BLMs). The efficient ion transport was investigated by both a fluorescence-based vesicle assay and a planar bilayer conductance measurement, and M2 with diethylene glycol substitution exhibited more efficient activity comparable to amphotericin B. Moreover, the presence of a photosensitive o-nitrobenzyl group provided the light-regulation to deactivate ion transport by destroying the channel assembly of the molecules in BLMs, which provides new opportunities for developing intelligent light-regulated systems for biomedical applications based on synthetic small molecules. † Electronic supplementary information (ESI) available: The detailed synthesis and characterizations of compounds, self-assembled properties, some HPTS assays, doping and solubility measurements. See

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Section: Resultsmentioning

confidence: 99%

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Meng

Lin

et al. 2015

New J. Chem.

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“…[5][6][7] Barrel-stave systems, [8] G-quadruplex, [9] lariat crown ethers, [10] hydraphiles [11] or peptide-appended crownethers [12,13] have been intensively used to construct ion-channels for selective ionic translocation. [15] We know from our previous studies,t hat lipophilic ureido crown ethers disrupt the bilayer membrane at low concentration, showing rare single channel openings. [14] This approach has been extended to light-responsive channels,a nd the structure-activity relationships have been determined.…”

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Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels

et al. 2015

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The bacterial KcsA channel conducts K + cations at high rates while excluding Na + cations.H erein, we report an artificial ion-channel formed by H-bonded stacks of crownethers,w here K + cation conduction is highly preferred to Na + cations.T he macrocycles aligned along the central pore surround the K + cations in as imilar manner to the water around the hydrated cation, compensating for the energetic cost of their dehydration. In contrast, the Na + cation does not fit the macrocyclic binding sites,s oi ts dehydration is not completely compensated. The present highly K + -selective macrocyclic channel may be regarded as ab iomimetic of the KcsA channel.

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“…[14] This approach has been extended to light-responsive channels,a nd the structure-activity relationships have been determined. [15] We know from our previous studies,t hat lipophilic ureido crown ethers disrupt the bilayer membrane at low concentration, showing rare single channel openings. At higher concentration, ar ich array of interconverting channel conductance states are observed for K + cations.T he channels arise from H-bonded stacks of crown ethers where transport of cations would occur by the macrocycles around acentral large pore.…”

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confidence: 99%

Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels

et al. 2015

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The bacterial KcsA channel conducts K(+) cations at high rates while excluding Na(+) cations. Herein, we report an artificial ion-channel formed by H-bonded stacks of crown-ethers, where K(+) cation conduction is highly preferred to Na(+) cations. The macrocycles aligned along the central pore surround the K(+) cations in a similar manner to the water around the hydrated cation, compensating for the energetic cost of their dehydration. In contrast, the Na(+) cation does not fit the macrocyclic binding sites, so its dehydration is not completely compensated. The present highly K(+)-selective macrocyclic channel may be regarded as a biomimetic of the KcsA channel.

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Self-assembly of crown ether-based amphiphiles for constructing synthetic ion channels: the relationship between structure and transport activity

Abstract: Efficient ion transport was achieved from crown ether amphiphile-based ion channels by simply regulating the molecular structures.

Cited by 26 publications

References 45 publications

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels

Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels

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Self-assembly of crown ether-based amphiphiles for constructing synthetic ion channels: the relationship between structure and transport activity

Abstract: Efficient ion transport was achieved from crown ether amphiphile-based ion channels by simply regulating the molecular structures.

Cited by 26 publications

References 45 publications

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes

Highly Selective Artificial Cholesteryl Crown Ether K+‐Channels

Highly Selective Artificial Cholesteryl Crown Ether K+‐Channels

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Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels

Highly Selective Artificial Cholesteryl Crown Ether K⁺‐Channels