Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

Simone, Nicola Alessandro De; Chvojka, Matúš; Lapešová, Jana; Martínez‐Crespo, Luis; Slávik, Petr; Sokolov, Jan; Butler, Stephen J.; Valkenier, Hennie; Šindelář, Vladimír

doi:10.1021/acs.joc.2c00870

Cited by 10 publications

(14 citation statements)

References 46 publications

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“…Although with this method all the transporters showed similar activity, mechanistic studies revealed that bambusuril 35 d was clearly the most active transporter via a classical HCO 3 − /Cl − antiport mechanism (see Section 4.2 for a detailed discussion on mechanistic studies). Moreover, this compound also showed the best activity in HCO 3 − uniport experiments and performed in a follow‐up study with more bambusurils still the best, together with 35 k [88] . The special character of the bambusuril binding site (formed by polarized CH groups), the high anion affinity, the large degree of fluorination, and the possibility to accommodate two anions in its binding site are features that probably contribute to the exceptional transport properties of these fluorinated bambusurils.…”

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 85%

“…Monofunctionalised analogues of 35 c and 35 d were also prepared and conjugated to cholic acid and crown‐ether moieties ( 35 e – k ). [88] These substituents showed only a marginal effect on the transport properties of the bambusurils. Bambusurils represent one of the most active and selective families of bicarbonate transporters (see Sections 3.5 and 4.1 for extended discussions).…”

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

“…Bambusurils are neutral compounds that bear twelve polarized CH groups pointing to the interior of a cavity that can bind anions very efficiently. Monofunctionalised analogues of 35 c and 35 d were also prepared and conjugated to cholic acid and crown‐ether moieties ( 35 e – k ) [88] . These substituents showed only a marginal effect on the transport properties of the bambusurils.…”

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

“…Moreover, this compound also showed the best activity in HCO 3 − uniport experiments and performed in a follow‐up study with more bambusurils still the best, together with 35 k . [88] The special character of the bambusuril binding site (formed by polarized CH groups), the high anion affinity, the large degree of fluorination, and the possibility to accommodate two anions in its binding site are features that probably contribute to the exceptional transport properties of these fluorinated bambusurils.…”

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

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Transmembrane Transport of Bicarbonate by Anion Receptors

Martínez‐Crespo

Valkenier

2022

ChemPlusChem

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The development of synthetic anion transporters is motivated by their potential application as treatment for diseases that originate from deficient anion transport by natural proteins. Transport of bicarbonate is important for crucial biological functions such as respiration and digestion. Despite this biological relevance, bicarbonate transport has not been as widely studied as chloride transport. Herein we present an overview of the synthetic receptors that have been studied as bicarbonate transporters, together with the different assays used to perform transport studies in large unilamellar vesicles. We highlight the most active transporters and comment on the nature of the functional groups present in active and inactive compounds. We also address recent mechanistic studies that have revealed different processes that can lead to net transport of bicarbonate, as well as studies reported in cells and tissues, and comment on the key challenges for the further development of bicarbonate transporters.

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Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 85%

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

Section: Overview Of Synthetic Bicarbonate Transportersmentioning

confidence: 99%

See 2 more Smart Citations

Transmembrane Transport of Bicarbonate by Anion Receptors

Martínez‐Crespo

Valkenier

2022

ChemPlusChem

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“…Monofunctionalised analogues of 35c and 35d were also prepared and conjugated to cholesterol and crown-ether moieties. 85 These substituents showed only a marginal effect on the transport properties of the bambusurils. Bambusurils represent one of the most active and selective families of bicarbonate transporters (see Sections 3.5 and 4.1 for extended discussions).…”

Section: Transporters Without Acidic Nh or Oh Groupsmentioning

confidence: 99%

Transmembrane transport of bicarbonate by anion receptors

Martínez‐Crespo

Valkenier

2022

Preprint

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The development of synthetic anion transporters is motivated by their potential application as treatment for diseases that originate from deficient anion transport by natural proteins. Transport of bicarbonate is important for crucial biological functions such as respiration and digestion. Despite this biological relevance, bicarbonate transport has not been as widely studied as chloride transport. Herein we present an overview of the synthetic receptors that have been studied as bicarbonate transporters, together with the different assays used to perform transport studies in large unilamellar vesicles. We highlight the most active transporters and comment on the nature of the functional groups present in active and inactive compounds. We also address recent mechanistic studies that have revealed different processes that can lead to net transport of bicarbonate, as well as studies reported in cells and tissues and comment on the key challenges for the further development of bicarbonate transporters.

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Tuning CH Hydrogen Bond‐Based Receptors toward Picomolar Anion Affinity via the Inductive Effect of Distant Substituents

Chvojka,

Madea,

Valkenier

et al. 2023

Angewandte Chemie

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Inspired by nature, artificial hydrogen bond‐based anion receptors have been developed to achieve high anion selectivity; however, their binding affinity is usually low. The potency of these receptors is usually increased by the introduction of aryl substituents, which withdraw electrons from their binding site through the resonance effect. Here, we show that the polarization of the C(sp3)‐H binding site of bambusuril receptors, and thus their potency to bind anions, can be modulated by the inductive effect. The presence of electron‐withdrawing groups on benzyl substituents of bambusurils significantly increases their binding affinities to halides, resulting in the strongest iodide receptor reported to date with an association constant greater than 1013 M−1 in acetonitrile. A Hammett plot showed that while the bambusuril affinity toward halides linearly increases with the electron‐withdrawing power of their substituents, their binding selectivity remains essentially unchanged.

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Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

Cited by 10 publications

References 46 publications

Transmembrane Transport of Bicarbonate by Anion Receptors

Transmembrane Transport of Bicarbonate by Anion Receptors

Transmembrane transport of bicarbonate by anion receptors

Tuning CH Hydrogen Bond‐Based Receptors toward Picomolar Anion Affinity via the Inductive Effect of Distant Substituents

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