Tetracationic-to-dianionic tetraamino-dihydroxy-tetraoxacalix[4]arene: A paraquat receptor for all seasons

Mancuso, Francesca; Crisafulli, Daniele; Milone, Marco; Irto, Anna; Cigala, Rosalia Maria; Lando, Gabriele; Pisagatti, Ilenia; Notti, Anna; Gattuso, Giuseppe

doi:10.1016/j.molliq.2022.120670

Cited by 4 publications

(1 citation statement)

References 46 publications

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“…These two reversed effects cause a significant decrease of P

{{_{{\rm Cl}{^{- }}}}}

/ P

{{_{{\rm K}{^{+}}}}}

ratio. At pH=9, in addition to the influence of terminal carboxyl groups, the partial deprotonation of phenol hydroxyl groups (p K a =8.21 [56] ) might also contribute to the weak cation selectivity of 1 . The partially deprotonated hydroxyl groups could increase the affinity of the macrocycle towards K + and diminish the association of Cl − .…”

Section: Figurementioning

confidence: 99%

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

Huang

Wang

et al. 2023

Angewandte Chemie

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Inspired by the unique structure and function of the natural chloride channel (ClC) selectivity filter, we present herein the design of a ClC‐type single channel molecule. This channel displays high ion transport activity with half‐maximal effective concentration, EC50, of 0.10 μM, or 0.075 mol % (channel molecule to lipid ratio), as determined by fluorescent analysis using lucigenin‐encapsulated vesicles. Planar bilayer lipid membrane conductance measurements indicated an excellent Cl−/K+ selectivity with a permeability ratio P Cl- ${{_{{\rm Cl}{^{- }}}}}$ /P K+ ${{_{{\rm K}{^{+}}}}}$ up to 12.31, which is comparable with the chloride selectivity of natural ClC proteins. Moreover, high anion/anion selectivity (P Cl- ${{_{{\rm Cl}{^{- }}}}}$ /P Br- ${{_{{\rm Br}{^{- }}}}}$ =66.21) and pH‐dependent conductance and ion selectivity of the channel molecule were revealed. The ClC‐like transport behavior is contributed by the cooperation of hydrogen bonding and anion–π interactions in the central macrocyclic skeleton, and by the existence of pH‐responsive terminal phenylalanine residues.

show abstract

“…These two reversed effects cause a significant decrease of P

{{_{{\rm Cl}{^{- }}}}}

/ P

{{_{{\rm K}{^{+}}}}}

Section: Figurementioning

confidence: 99%

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

Huang

Wang

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

Huang

Wang

et al. 2023

Angew Chem Int Ed

View full text Add to dashboard Cite

Inspired by the unique structure and function of the natural chloride channel (ClC) selectivity filter, we present herein the design of a ClC-type single channel molecule. This channel displays high ion transport activity with half-maximal effective concentration, EC 50 , of 0.10 μM, or 0.075 mol % (channel molecule to lipid ratio), as determined by fluorescent analysis using lucigenin-encapsulated vesicles. Planar bilayer lipid membrane conductance measurements indicated an excellent Cl À /K + selectivity with a permeability ratio P Cl À /P K þ up to 12.31, which is comparable with the chloride selectivity of natural ClC proteins. Moreover, high anion/anion selectivity (P Cl À /P Br À = 66.21) and pHdependent conductance and ion selectivity of the channel molecule were revealed. The ClC-like transport behavior is contributed by the cooperation of hydrogen bonding and anion-π interactions in the central macrocyclic skeleton, and by the existence of pH-responsive terminal phenylalanine residues.

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A fluorescent receptor for alkylammonium ions based on an anthryl-linked triazole-modified hexahomotrioxacalix[3]arene

Rahman

Jiang

et al. 2023

Journal of Molecular Structure

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Tetracationic-to-dianionic tetraamino-dihydroxy-tetraoxacalix[4]arene: A paraquat receptor for all seasons

Cited by 4 publications

References 46 publications

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

An Artificial Single Molecular Channel Showing High Chloride Transport Selectivity and pH‐Responsive Conductance

A fluorescent receptor for alkylammonium ions based on an anthryl-linked triazole-modified hexahomotrioxacalix[3]arene

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