Self-assembled anion channel formation by bis(1,3-propanediol)-linked <i>meta</i>-dipropynylbenzene-based small molecules

Vijay, Amal; Chattopadhayay, Sandip; Mukherjee, Arnab; Talukdar, Pinaki

doi:10.1039/d2cc05155a

Cited by 8 publications

(4 citation statements)

References 28 publications

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“…Cholesterol loading will decrease the fluidity of the membrane, which will decrease the number of ions transported by the carrier mechanism [54] . The effectiveness of the supramolecular channel transit, however, will not change significantly [55] . The experimental results showed that the transport activity remained essentially unchanged in the presence of cholesterol (Figure S13), clearly indicating that the channel construction is responsible for the ion transport process.…”

Section: Resultsmentioning

confidence: 99%

“…[54] The effectiveness of the supramolecular channel transit, however, will not change significantly. [55] The experimental results showed that the transport activity remained essentially unchanged in the presence of cholesterol (Figure S13), clearly indicating that the channel construction is responsible for the ion transport process. The realtime channel current of compound 1 b was monitored using diphytanoyl phosphatidylcholine (diPhyPC) bilayer lipid membrane (BLM).…”

Section: Methodsmentioning

confidence: 93%

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Supramolecular Barrel‐Rosette Ion Channel Based on 3,5‐Diaminobenzoic Acid for Cation‐Anion Symport

Chattopadhayay,

Ghosh,

Kumar Mukhopadhyay

et al. 2023

Angew Chem Int Ed

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The structural tropology and functions of natural cation‐anion symporting channels have been continuously investigated due to their crucial role in regulating various physiological functions. To understand the physiological functions of the natural symporter channels, it is vital to develop small molecule‐based biomimicking systems that can provide mechanistic insights into the ion‐binding sites and the ion‐translocation pathways. Herein, we report a series of bis((R)‐(‒)‐mandelic acid)‐linked 3,5‐diaminobenzoic acid‐based self‐assembled ion channels with distinctive ion transport ability. Ion transport experiment across the lipid bilayer membrane revealed that compound 1b exhibits the highest transport activity among the series, and it has interesting selective co‐transporting functions, i.e., facilitates K+/ClO4‒ symport. Electrophysiology experiments confirmed the formation of supramolecular ion channels with an average diameter of 6.2 ± 1 Å and single channel conductance of 57.3 ± 1.9 pS. Selectivity studies of channel 1b in BLM demonstrated the permeability ratio of PCl‒/PK+ = 0.053 ±0.02, PClO4‒/PCl‒ = 2.1 ± 0.5, and PK+/PNa+ = 1.5 ± 1, respectively, indicating the higher selectivity of the channel towards KClO4 over KCl salt. A hexameric assembly of a trimeric rosette of 1b was subjected to molecular dynamics simulations with different salts to understand the supramolecular channel formation and ion selectivity pattern.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 93%

Supramolecular Barrel‐Rosette Ion Channel Based on 3,5‐Diaminobenzoic Acid for Cation‐Anion Symport

Chattopadhayay,

Ghosh,

Kumar Mukhopadhyay

et al. 2023

Angew Chem Int Ed

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“…Meanwhile, activities in developing new types of anion-selective channels continue unabated. 161,166,167 In 2020, Roy et al reported a fully hydrogen-bonded, helicallyfolded aromatic foldamer-based synthetic channel, with a central lumen rendered by the many methyl groups 161 (Fig. 7(b)).…”

Section: Synthetic Channelsmentioning

confidence: 99%

Lipid vesicle-based molecular robots

Peng,

Iwabuchi,

Izumi

et al. 2024

Lab Chip

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“…To identify the kind of ion transport mechanism (carrier or channel), a cholesterol assay was conducted. [56,57] The fluidity of the membrane will be reduced by cholesterol loading, which will reduce the number of ions carried by the carrier mechanism. However, there would be no significant change in how well the supramolecular channel transit works.…”

Section: Evidence Of Ion Channel Mechanismmentioning

confidence: 99%

A Halogen‐Bond‐Driven Artificial Chloride‐Selective Channel Constructed from 5‐Iodoisophthalamide‐based Molecules

Sharma,

Sarkar,

Chattopadhayay

et al. 2024

Angewandte Chemie

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Despite considerable emphasis on advancing artificial ion channels, progress is constrained by the limited availability of small molecules with the necessary attributes of self‐assembly and ion selectivity. In this study, a library of small molecules based on 5‐haloisophthalamide and a non‐halogenated isophthalamide were examined for their ion transport properties across the lipid bilayer membranes, and the finding demonstrates that the di‐hexyl‐substituted 5‐iodoisophthalamide derivative exhibits the highest level of activity. Furthermore, it was established that the highest active compound facilitates the selective chloride transport that occurs via an antiport‐mediated mechanism. The crystal structure of the compound unveils a distinctive self‐assembly of molecules, forming a zig‐zag channel pore that is well‐suited for the permeation of anions. Planar bilayer conductance measurements proved the formation of chloride selective channels. A molecular dynamics simulation study, relying on the self‐assembled component derived from the crystal structure, affirmed the paramount significance of intermolecular hydrogen bonding in the formation of supramolecular barrel‐rosette structures that span the bilayer. Furthermore, it was demonstrated that the transport of chloride across the lipid bilayer membrane is facilitated by the synergistic effects of halogen bonding and hydrogen bonding within the channel.

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Self-assembled anion channel formation by bis(1,3-propanediol)-linked meta-dipropynylbenzene-based small molecules

Abstract: Two self-assembled barrel-rosette ion channels have been developed using bis(1,3-propanediol)-linked m-dipropynylbenzene-based molecules. The system with an additional amide arm acted as a better channel compared to that having an ester...

Cited by 8 publications

References 28 publications

Supramolecular Barrel‐Rosette Ion Channel Based on 3,5‐Diaminobenzoic Acid for Cation‐Anion Symport

Supramolecular Barrel‐Rosette Ion Channel Based on 3,5‐Diaminobenzoic Acid for Cation‐Anion Symport

Lipid vesicle-based molecular robots

A Halogen‐Bond‐Driven Artificial Chloride‐Selective Channel Constructed from 5‐Iodoisophthalamide‐based Molecules

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