A Highly Active Anion‐Selective Aminocyclodextrin Ion Channel

Madhavan, Nandita; Robert, Erin C.; Gin, Mary S.

doi:10.1002/anie.200501625

Cited by 140 publications

(92 citation statements)

References 46 publications

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“…Lehn and coworkers [11] suggested grafting oligo(ethylene oxide) derivatives on CDs in order to form bolaamphiphilic star polymers with controlled solubility in water. More recently, this approach was also used by Madhavan et al, [13] who grafted oligomers of poly(tetrahydrofuran) on one side of a b-CD. The molecular weight of that hydrophobic oligomer was adjusted to be able to span an entire lipid bilayer.…”

mentioning

confidence: 94%

Synthesis of Half‐Channels by the Anionic Polymerization of Ethylene Oxide Initiated by Modified Cyclodextrin

Badi¹,

Auvray²,

Guégan³

2009

Advanced Materials

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Amphiphilic star‐shaped oligomers are produced by anionic polymerization of ethylene oxide (EO) using per‐2,3‐di‐O‐heptyl‐β‐(or γ)cyclodextrins as initiators — a versatile way of synthesizing artificial channels bearing one polyEO branch per glucose unit. The behavior of the amphiphilic molecules in lipid membranes is studied by electrical measurements, which confirms the formation of transient, well‐defined dimeric ionic channels (see figure).

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mentioning

confidence: 94%

Synthesis of Half‐Channels by the Anionic Polymerization of Ethylene Oxide Initiated by Modified Cyclodextrin

Badi¹,

Auvray²,

Guégan³

2009

Advanced Materials

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“…[7] These possibilities have stimulated recent interest in the design and study of synthetic anion transporters. [8] The work has encompassed self-assembling channels, [9] monomeric channels [10] and receptors acting as mobile carriers.…”

Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

McNally¹,

Koulov²,

Lambert³

et al. 2008

Chemistry A European J

119

111

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Chloride transport by a series of steroid-based "cholapod" receptors/carriers was studied in vesicles. The principal method involved preincorporation of the cholapods in the vesicle membranes, and the use of lucigenin fluorescence quenching to detect inward-transported Cl − . The results showed a partial correlation between anion affinity and transport activity, in that changes at the steroidal 7 and 12 positions affected both properties in concert. However, changes at the steroidal 3-position yielded irregular effects. Among the new steroids investigated the bis-p-nitrophenylthiourea 3 showed unprecedented activity, giving measurable transport through membranes with a transporter/lipid ratio of 1:250 000 (an average of <2 transporter molecules per vesicle). Increasing transporter lipophilicity had no effect, and positively charged steroids had low activity. The p-nitrophenyl monourea 25 showed modest but significant activity. Measurements using a second method, requiring the addition of transporters to preformed vesicle suspensions, implied that transporter delivery was problematic in some cases. A series of measurements employing membranes of different thicknesses provided further evidence that the cholapods act as mobile anion carriers.

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“…8) reported by the group of M.S. Gin [60]. The ionophore was obtained decorating the lower rim of a -cyclodextrin with sevenamino pentabutyleneglycols.…”

Section: Channel Forming Artificial Anion Transport-ersmentioning

confidence: 94%

Artificial Anion Transporters in Bilayer Membranes

Licen¹,

Riccardis²,

Izzo³

et al. 2008

CDDT

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Anion transport across phospholipid membrane is a typical supramolecular function involving dynamic recognition of the substrate during the whole translocation process. Supramolecular chemists, taking inspiration by the natural anion transporters, have designed artificial systems able to mimic, at the functional level, several features of the natural ion channels. The scope of this research is twofold: on one hand to get insight on the molecular basis of recognition and transport, and on the other hand to get control of the biomedical relevant processes. The present review focuses on the synthetic systems promoting anion transport, covering both artificial channels and carriers that operate in phospholipid membrane. The design principles of such systems will be discussed together with the potential biomedical applications.

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A Highly Active Anion‐Selective Aminocyclodextrin Ion Channel

Cited by 140 publications

References 46 publications

Synthesis of Half‐Channels by the Anionic Polymerization of Ethylene Oxide Initiated by Modified Cyclodextrin

Synthesis of Half‐Channels by the Anionic Polymerization of Ethylene Oxide Initiated by Modified Cyclodextrin

Structure–Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning

Artificial Anion Transporters in Bilayer Membranes

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