Semithiobambus[6]uril is a transmembrane anion transporter

Lang, C. Max; Mohite, Amar R.; Deng, Xiaoli; Yang, Fan; Dong, Zeyuan; Xu, Jing; Keinan, Ehud; Reany, Ofer

doi:10.1039/c7cc04026a

Cited by 37 publications

(29 citation statements)

References 52 publications

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“…A list of reported bambusuril derivatives is shown in Figure 3. [21][22][23][24] These macrocycles are not further discussed here as they are subject of a separate review. While (Me)BU [6] is apparently insoluble in any solvent, replacement of the methyl groups with a benzyl groups resulted in millimolar bambusuril solubilities in chloroform and DMSO.…”

Section: Bambusuril Structure and Propertiesmentioning

confidence: 99%

Bambusuril Anion Receptors

Lízal

Šindelář

2017

Israel Journal of Chemistry

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Bambusurils are macrocyclic compounds whose synthesis was first reported in 2010. Since then bambusurils have been investigated mainly because of its six‐membered homologues’ outstanding binding affinities towards inorganic anions in both organic solvents and water. Here we summarize the most important aspects of bambusuril chemistry. Basic characteristics of bambusurils are presented, followed by details of their synthesis, and a discussion of their supramolecular properties, with an emphasis on binding in water. Potential applications of bambusurils are highlighted at the end of the review.

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Section: Bambusuril Structure and Propertiesmentioning

confidence: 99%

Bambusuril Anion Receptors

Lízal

Šindelář

2017

Israel Journal of Chemistry

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“…[4] Recently, we studied the anion transporting efficiency of all three analogs by monitoring the influx of chloride ions across a lipid membrane, using semiaza-BU [4] as control. [51] Upon addition of the potential transporter, the influx of chloride ions was evaluated by monitoring the fluorescence intensity of lucigenin ( Figure 12A). [52] As shown in Figure 12B, semithio-BU [6] is a remarkably more efficient chloride transporter than BU [6] and semiaza-BU [6] in both relative and absolute terms.…”

Section: Selective Transmembrane Anion Transportmentioning

confidence: 99%

Hetero‐Bambusurils

Reany

Mohite

Keinan

2018

Israel Journal of Chemistry

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Synthetic anion carriers are essential for studying natural ion transporters and channels and for useful applications, such as treatment of channelopathies, supramolecular architecture, anion sensing and catalysis. Driven by the hypothesis that replacement of oxygen atoms in bambusurils (BUs) by other heteroatoms could significantly modify their anion binding properties, we calculated their molecular electrostatic potential and found a general trend of anion‐affinity: S>O>NH. We confirmed these predictions experimentally by synthesizing semithio‐ and semiaza‐BUs and studying their binding and transport properties. Although all analogs are excellent anion binders, only semithio‐bambus[6]uril is an effective transmembrane transporter capable of polarizing lipid membranes through selective anion uniport. Semiaza‐BUs exhibit simultaneous accommodation of three anions, linearly positioned along the main symmetry axis, which is reminiscent of natural chloride channels in E. coli.

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“…[41][42][43] Recently, a semi-thiobambus [6]uril was shown to function as an anion carrier, albeit not as efficiently as the biotin [6]uril macrocycles. 44 Based on the high anion affinities found for bambusuril 1 (Scheme 1), 45 high selectivities observed in binding, 46 the high degree of encapsulation of anions, and their polarized but non-acidic CH groups involved in anion binding, 47 we expected bambus [6]urils to be potentially very selective anion carriers. Fluorinated groups were introduced with the aim of enhancing rates of transport, yielding three new fluorinated bambus [6]urils (Scheme 1, 2-4).…”

Section: Introductionmentioning

confidence: 99%

Fluorinated Bambusurils as Highly Effective and Selective Transmembrane Cl−/HCO3− Antiporters

Valkenier

Akrawi

Jurček

et al. 2019

Chem

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ArticleFluorinated Bambusurils as Highly Effective and Selective Transmembrane Cl À /HCO 3 À Antiporters Synthetic anion receptors can be used to transport ions across membranes. In this work, bambusuril macrocycles are demonstrated to be very efficient in exchanging chloride and bicarbonate ions, whereas exchange with nitrate is much slower. This is explained by the anion binding properties of the receptor. The high rates of transport by these bambusurils and mechanistic insight provided here represent an advancement toward the future therapeutic applications of synthetic anion carriers.

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Semithiobambus[6]uril is a transmembrane anion transporter

Cited by 37 publications

References 52 publications

Bambusuril Anion Receptors

Bambusuril Anion Receptors

Hetero‐Bambusurils

Fluorinated Bambusurils as Highly Effective and Selective Transmembrane Cl−/HCO3− Antiporters

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