Copillar[5]arene Chemistry: Synthesis and Applications

Vincent, Stéphane; Chen, Wenzhang

doi:10.1055/s-0040-1738369

Cited by 1 publication

(2 citation statements)

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“…15 Vincent et al already explored the complex multifunctional carbohydrate decorated PA-molecules, 38−42 that can also exhibit specific properties for applications in materials science 43 or chemical biology providing a great insights on the synthesis paths for designing such molecules and their strategic incorporation to optimize their drug delivery properties. 44 Pursuing our endeavors in designing original supramolecular channels with efficient and selective transport properties, we recently became interested in the possibility of grafting saccharide residues on both rims of the PA platforms. From our previous experience we know that PA AWCs present a central hydrophobic cavity of ∼5 Å which is big enough to allow the passage of ions according to their hydration energy.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Barboiu et al have studied the crown-ether-pillar[5]arenes in selective transport of K + cations and more recently described H-bonded dimeric rim-differentiated PAs with great water transport activity and total ion rejection . Vincent et al already explored the complex multifunctional carbohydrate decorated PA-molecules, − that can also exhibit specific properties for applications in materials science or chemical biology providing a great insights on the synthesis paths for designing such molecules and their strategic incorporation to optimize their drug delivery properties …”

Section: Introductionmentioning

confidence: 99%

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Proton- versus Cation-Selective Transport of Saccharide Rim-Appended Pillar[5]arene Artificial Water Channels

Andrei,

Chen,

Baaden

et al. 2023

J. Am. Chem. Soc.

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Transport of water across cell membranes is a fundamental process for important biological functions. Herein, we focused our research on a new type of symmetrical saccharide rim-functionalized pillar[5]arene (PA-S) artificial water channels with variable pore structures. To point out the versatility of PA-S channels, we systematically varied the nature of anchoring/gate keepers d-mannoside, d-mannuronic acid, or sialic acid H-bonding groups on lateral pillar[5]arene (PA) arms, known as good membrane adhesives, to best describe the influence of the chemical structure on their transport activity. The control of hydrophobic membrane binding–hydrophilic water binding balance is an important feature influencing the channels’ structuration and efficiency for a proper insertion into bilayer membranes. The glycosylated PA channels’ transport performances were assessed in lipid bilayer membranes, and the channels were able to transport water at high rates (∼106–107 waters/s/channel within 1 order of magnitude as for aquaporins), serving as selective proton railways with total Na+ and K+ rejection. Molecular simulation substantiates the idea that the PAs can generate supramolecular pores, featuring hydrophilic carbohydrate gate-keepers that serve as water–sponge relays at the channel entrance, effectively absorbing and redirecting water within the channel. The present channels may be regarded as a rare biomimetic example of artificial channels presenting proton vs cation transport selectivity performances.

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Section: ■ Introductionmentioning

confidence: 99%