# Partitioning / Self-assembly of Artificial Water Channels
– Toward Controlled Permselectivity through Bilayer
Membrane

Dan-Dan Su, Arie van Der Lee, Mihail Barboiu

► To cite this version:

Dan-Dan Su, Arie van Der Lee, Mihail Barboiu. Partitioning / Self-assembly of Artificial Water Channels – Toward Controlled Permselectivity through Bilayer Membrane. Angewandte Chemie International Edition, 2024, 64 (1), pp.e202413816. 10.1002/anie.202413816. hal-05083496

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# Partitioning / Self-assembly of Artificial Water Channels – Toward Controlled Permselectivity through Bilayer Membrane

Dan-Dan Su, Arie van der Lee, and Mihail Barboiu*

**Abstract:** Artificial water channels (AWCs) have been extensively explored to mimic natural proteins, which enables to effectively transport water while blocking ions. As one of the first AWCs, self-assembled I-quartets (HCx) have showcased high water-permselectivity that can be enhanced by improving their distribution and stability within membrane. The use of long alkyl chains (n > 8) is constrained by their low solubility and aggregation. Herein, we considered cycloalkyl moieties, explored for the increase of the solubility favoring enhanced partition and/ for their self-assembly behaviors resulting the formation of effective stable water-channels with increased water permeability in bilayer membranes. This class of cycloalkyl-ureido-ethyl-imidazole amphiphilic (CxUH) channel could serve as a new reference for the effective design of self-assembled artificial water channels, it may give rise to the applications in desalination or in water treatment.

Artificial water channels – AWCs[1,2] such as pillar-[n]arenes,[3] foldamers,[4] helical peptides[5] carbon nanotubes,[6] and macrocycles[7], have been extensively studied over the past decades. Taking advantage of their common hollow tubular superstructures, water molecules can be readily accommodated inside the channels through water-water or water-channel hydrogen (H) bonding interactions. The channels possess narrow interior diameters ranging from 0.3 to 1.9 nm where a selective ultrafast water wire or cluster permeation occurs. The pore water flow translocation is strongly regulated by the inner surface of the channel, where water clusters are stabilized and optimally H-bonded, resulting in enhanced permeability. The entire channel also need a favorable and directionally

correct membrane insertion for which hydrophobic groups at the interface with lipid membranes are of extreme importance for the optimal channel partitioning, aggregation, and its dynamics behavior within the membrane.

Our group has pioneered this field by reporting the I-quartet (HCx) AWC with a pore size of 2.6 Å, which accommodates confined H-bonded water wires similar to those found in natural Aquaporins.[8] Beyond this, H-bonds among vicinal urea units play a vital role in the monomer stacking and directional self-assembly of hollow channel architectures. Of particular important are the alkyl chains at the interface with the bilayer membrane, which through their controlled lipid affinity, contribute to the stabilization and dynamics of the channel during water translocation. These alkyl chains, varying from butyl-, pentyl-, hexyl-, heptyl-, octyl-, and octadecyl-,[9] to chiral[10] or bis-alkyl chains,[11] have been shown to improve the net permeability of water by an order of magnitude, making hydrophobicity a key factor in optimizing channel performances. Notably, longer alkyl chains enhance the stability of single-channel architectures within bilayer membranes, even at lower concentration. Further dispersion of pre-aggregated I-quartets in polyamide membranes has been carried out on a lab/ prototype scale for water desalination.[12] Defect-free membranes has been achieved using hexyl- or octyl I-quartets, owing to their optimal solubility and aggregation in common solvents. Inspired by these works, we explored a different class of hydrophobic tails-cycloalkyl groups, which are rarely used in liposome transport assays. These groups are expected to promote compact packing and organization of channels within the membrane compared to their linear counterparts with similar hydrophobicity. Especially, cyclo-alkyl amines have been reported to display superior permeation property across liquid, bilayer or cell membranes.[13]

Herein, we investigate the self-assembly and membrane transport properties of amphiphilic cycloalkyl-ureido-ethyl-imidazoles (CxUH), synthesized using triphosgene-amine or isocyanate-amine chemistries (Scheme 1). We postulate that CxUH compounds will induce the self-assembly of urea/ imidazole H-bonding pores, encased by a densely packed layer of hydrophobic cycloalkyl groups. The distribution of H-bonding and hydrophobic shells may overall lead to effective CxUH channels, capable of high water translocation, making them promising platforms for AWCs. The research described here is about understanding how these channels are operating within membranes and should provide informations to improve their transport performances. The novel objective here is to understand and

<figure><img src="image_3.png" /></figure>

<footnote>[*] Dr. D.-D. Su, Dr. A. van der Lee, Dr. M. Barboiu
Institut Européen des Membranes, Adaptive Supramolecular Nanosystems Group, University of Montpellier, ENSCM, CNRS.
Place Eugène Bataillon, CC 047, F-34095, Montpellier, France.
E-mail: mihail-dumitru.barboiu@umontpellier.fr</footnote>

<footnote>Dr. M. Barboiu
Babes-Bolyai University, Supramolecular Organic and Organometallic Chemistry Center (SOOMCC), Cluj-Napoca, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania.</footnote>

<footnote>© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</footnote>
<figure><img src="image_4.png" /><figcaption>**Scheme 1.** Chemical structures of cycloalkyl-ureido-ethyl-imidazoles (CxUH).</figcaption></figure>

corelate the self-assembly behaviors with permeabilities and performances.

**X-ray single-crystal structure.** Colorless single crystals of **C5UH**, **C6UH** and **AUH**[14] were obtained from methanol/water solutions, and subjected to X-ray diffraction analysis. The crystal structures of **C5UH** and **C6UH** reveal the formation of dimers (Figure 1a, b), via two intermolecular = N–H–N bonds ($d_{N...H}$ of 2.15 Å and 2.40 Å) between the =N atom of imidazole nitrogen of one molecule and the two urea H–N of a vicinal molecule. Further H-bonds ($d = 1.90$ Å) between the imidazole N–H moiety of one molecule and the urea carbonyl group of a neighboring molecule connect the vicinal dimers. Analysis of crystal structure of **AUH** reveals a homomeric urea-urea and imidazole-

<figure><img src="image_5.png" /><figcaption>**Figure 1.** (left) Crystal structures in stick representation and (right) side-view of the crystal packing of the heteromeric urea-imidazole H-bonding in a) (C5UH)2, b) (C6UH)2 dimers and packing of the homomeric urea-urea, and c) imidazole-imidazole H-bonding in AUH oligomers; Hydrogen-bonds: green dots.</figcaption></figure>

imidazole H-bonding. The NH–O=C– hydrogen bonds ($d_{O-H}$ of 2.10 and 2.40 Å) distances are consistent along the urea ribbon, and aligning with other urea systems (Figure 1c). Two neighboring urea planes are orthogonally disposed (approximately 90°) relative to each other, resulting in a zig-zag conformation, which contrasts with the planar conformation typically observed in the crystal structures of linear alkyl-ureido **HCx** compounds. Additional, NH–N=H– bonds ($d_{N...H}$ of 1.83 Å) between imidazole units of two different oligomers lead to the formation of double H-bonded layers. Interestingly, this mixed heteromeric urea-imidazole H-bonding is preferred in monocyclic **C5UH** and **C6UH** compounds, while independent homomeric urea-urea and imidazole-imidazole H-bonding is present in bicyclic bulky **AUH** compound. Moreover, all these H-bonding superstructures are alternatively stratified with hydrophobic layers of (bi)cyclic moieties in van der Waals contact (Figure 1a–c).[15]

These structures suggest that homo- or hetero H-bonding interactions of ureas and imidazoles can be structurally tuned by the spatial hydrophobic packing of monocyclic or bicyclic side arms for the generation of functional self-assembled channels within the bilayer membranes.

**Water transport experiments.** The water permeability of cyclic **CxUH** has been evaluated using the stopped-flow technique, which **CxUH**-embedded bilayer vesicles (Figure 2a) were prepared from a mixture of egg yolk phosphatidylcholine, brain phosphatidylserine, and cholesterol in a molar ratio of 4/1/5 in 200 mM sucrose osmolyte solution (10 mM phosphate buffered saline, pH 6.4). To induce vesicle shrinkage, a 400 mM sucrose solution was added to the extracellular solution, and the resulting change of light scattering signal was recorded to calculate water osmotic net permeability (*Pf*).

The water transport experiments revealed a dose-dependent transport behavior in the water net permeability of cycloalkyl compounds **C6UH**, **C8UH**, **M6UH** and **AUH**, whereas the linear compounds **HCx**, ($x=5-8$) exhibited lower permeabilities (Figure S19–S28). Notably, **C8UH** presents the highest net water permeability, reaching up to 8 µm/s, slightly surpassing the value of 7 µm/s for **C6UH** at mCLR = 1.82. As shown in Figure 2b, Cyclic **AUH** and **M6UH** showed a modest increase in water transport ability (3.5 µm/s) compared to their linear counterpart **HC6** (2.9 µm/s) at mCLR = 0.91. Differently, **C5UH** and **C7UH** displayed consistent dose-dependent transport, with net permeabilities of 5 µm/s and 3 µm/s respectively for each mCLR.

As a matter of fact, cyclic **CxUH** channels present the higher transport rates than the linear **HCx** I-quartet counterparts. For instance, **C8UH** showed a transport rate of 5.9 µm/s compared to 5 µm/s for **HC8**, and **C6UH** had a rate of 5.8 µm/s compared to 2.9 µm/s for **HC6**. Cyclic **CxUH** channels showed an overall net permeability sequence of **C8UH** > **C6UH** > **C5UH**, due to increased partitioning in bilayer membranes of channel-forming monomers with larger cycloalkyl tails and higher hydrophobicity (Table S1), as previously observed for linear I-quartet channels[8] or bis-
<figure><img src="image_6.png" /><figcaption>**Figure 2.** Schematic representation of a) CxUH channels within lipid bilayer; b) Net permeability of cyclic CxUH and linear HCx channels at 0.5 mM, mCLR = 0.91 (molar ratio of Compound to Lipid) through stopped-flow experiments. Error bars represent ± the standard deviation from the average of three independent samples, each sample were scanned through stopped-flow machine for ten to twenty times.</figcaption></figure>

alkyl ureido channels.[11] A sharper raise of the water net permeabilities was recorded for the **C6UH** and **C8UH** for a constantly increasing lipophilicity (log P) of the other compounds, (Figure S29). In the membranes the cyclohexyl or cyclooctyl are wrapping around I-quartets. Their permeability is not only the simple result of a linear increase of the log P values and it is going beyond the solubility behaviors via synergistic dynamic self-organization, which in turn results in correspondingly high-water conductivity through optimally stabilized and percolated channels.

The single-channel water permeabilities sequence of **HC6** > **AUH** > **C6UH** contrasts with the net permeability sequence of **HC6** < **AUH** < **C6UH**, (see Table S2) which in turn results in correspondingly high-water single conductivity through more stable but with less partition in the membrane of such aggregated channels. This can be explained that cyclic **CxUH** channels can exhibit superior transport behavior across cell membranes due to their increased solubility in the membranes compared to linear **HCx** channels. In a similar manner, the bicyclic **AUH** channels are less effective than monocyclic **C6UH** channels, showing improved single permeability due to their better stabilization within the membrane, but lower overall net permeability, likely due to less efficient solubility.

**Cation/anion and Proton-Transport Experiments.** We further evaluated the ion transport performances of CxUH compounds using HPTS (8-hydroxypyrene-1.3.6-trisulfonic acid trisodium salt) fluorescence assays with liposomes prepared from egg yolk L-α-phosphatidyl-choline for liposome preparation in KX (X⁻ = Cl⁻, Br⁻, I⁻, NO₃⁻, SO₄²⁻) or MCl (M⁺ = Cs⁺, Rb⁺, K⁺, Na⁺, H⁺) (100 mM) in phosphate buffer solution (PBS 10 mM, pH 6.4). Upon addition of a pH shock, ions and protons were exchanged through the inserted CxUH channels, meanwhile, altering the proportion of basic/acidic forms of HPTS in real-time. We had to note that the transportation of each proton is accompanied by a cation antiport or an anion symport, and vice versa. From these experiments, we can observe that there was no obvious selective transport of cations for most of CxUH channels, since their structuration is not effective to induce cation / H⁺ antiport conductance states at any studied concentrations (Figures 3a, S30–S36). Further assays were performed using electrogenic membrane polarization with valinomycin (Val) as a K⁺ carrier and FCCP as a proton carrier (Figure 3b). The HPTS proton tests were performed for CxUH and valinomycin, generated K⁺/H⁺ antiport rates through the channels. It was observed reasonable proton transport activities by coupling of valinomycin with the CxUH channels and generated a medium-low (C6UH, C7UH, C8UH, and AUH) or very low (C5UH and M6UH) activity.

The proton/chloride transport was further assessed[16,17] using patch clamp technique in unsymmetrical baths (cis

<figure><img src="image_7.png" /><figcaption>**Figure 3.** HPTS assay traced curves of C6UH channel at 0.5 mM a) by pH shock, and b) the ion transport in the presence of FCCP/valinomycin (Val).</figcaption></figure>
chamber = 0.25 M HCl; trans chamber = 0.1 M HCl, Figure S37-S42, Table 1). C5UH and M6UH exhibited $P_{H+}/P_{Cl-}$ values of 1.2 and 1.1, indicating no significant selectivity, consistent with their low activities observed in HPTS assays in the presence of FCCP compared to valinomycin. Regarding the other CxUH channels, the $P_{Cl-}/P_{H+}$ value of C8UH reached 71, and that of AUH ~31 being halved under negative voltage, even lower values for C6UH and C7UH. A higher $P_{H+}$ value indicate well-organized H-bonding water clusters which is beneficial for proton transport through the Grotthuss mechanism, a higher $P_{Cl-}$ value would indicate a less organized water network and permeation of large ions. Proton translocation is a structural diffusion through water clusters in CxUH channels is inversely correlated with single channel water permeability rather than channel insertion into bilayer membranes, as protons can translocate principally via directional H-bonds of stabilized and lower permeating water clusters within the channels.

This ratio can offer us informations about the selectivity and transport mechanisms of AWCs, and help us understand how the channels work within the bilayer membrane. The most performant AUH channels are observed as the best proton/chloride channel within this series with the highest conductance ~44 pS.

In recent years, self-assembled ion or water channels have been extensively studied with a biomimetic approach, aiming to replicate the functions, rather than the structure of natural proteins. Taking in consideration this idea, most of the research projects are dedicated to the optimal design of inner pore (super)structures that allow water H-bonding and translocation. The role of functional groups pointing toward the center of the channel was substantially proved as they strongly contribute to the formation and stabilization of water clusters at the channel entries. In the meantime, the external stabilization of single channels by hydrophobic shells at the bilayer membranes interface is of utmost importance bringing valuable insights into, a) the partition of the channels within the membrane, and b) the water re-organization ranging from a strongly organized single files to more dynamic semi-structured clusters, would represent the prerequisites for achieving high net permeability and selectivity.

The present study leads to the understanding of the key structural parameters that contribute to the optimal incorporation or stabilization of AWCs in lipid membranes. We reported a class of cycloalkyl-ureido-ethyl-imidazole amphiphilic CxUH channels that demonstrate enhanced water transport compared to their linear alkyl I-quartet counterparts. Overall, this work highlights the superior water transport rate and ion rejection capabilities of cycloalkyl water channels than I-quartet channels. It is especially noticeable that cyclohexyl compound C6UH exhibits a net permeability of 5.8 µm/s, which is twice that of the hexyl compound HC6. The contact is most probably favourable to cyclic tails for increasing their solubility in the bilayer membranes. On the contrary, the tendency for increasing the single water channel permeability and the proton translocation is not only the results of the linear increase in cyclic tail solubility in bilayer membranes. A lower net permeability was observed for bicyclic AUH channels where the more favorable wrapping of adamantyl tails tend to stabilize the channels, showing better water and proton single channels permeability.

These findings suggest that the CxUH channels offer a promising choice for the development of artificial water channels considering dynamic self-assembly and selective translocations, will be expected to apply into the applications of water treatment or purification and seawater desalination.

## Acknowledgements

This project was supported by Agence Nationale de la Recherche, project ANR-22-CE09-0006-03, CORNER-STONE and by the project "Evolution" funded by European Union - Nextgeneration EU and Romanian Government, under National Recovery and Resilience Plan for Romania, contract no.760033/23.05.2023 /23.05.2023, cod PNRR-C9-I8-CF16, through the Romanian Ministry of Research, Innovation and Digitalization, within Component 9, Investment I8".

## Conflict of Interest

The authors declare no conflict of interest.

## Data Availability Statement

The data that support the findings of this study are available from the corresponding author upon reasonable request.

**Keywords:** hydrogen bonding • hydrophobic effects • artificial water channels • self-assembly

<table><caption>**Table 1:** Proton/chloride permeability ratio and conductance $\gamma$ (pS) of CxUH channels.</caption><thead><tr><th>Channel</th><th>Selectivity</th><th>γ (pS)</th></tr></thead><tbody><tr><td>C5UH</td><td>H<sup>+</sup>/Cl<sup>-</sup> = 1.2</td><td>15</td></tr><tr><td>M6UH</td><td>H<sup>+</sup>/Cl<sup>-</sup> = 1.1</td><td>1.6</td></tr><tr><td rowspan="2">C6UH</td><td>Cl<sup>-</sup>/H<sup>+</sup> = 6.5 (-)<sup>[a]</sup></td><td>7(-)<sup>[a]</sup></td></tr><tr><td>Cl<sup>-</sup>/H<sup>+</sup> = 10.5 (+)<sup>[b]</sup></td><td>25(+)<sup>[b]</sup></td></tr><tr><td rowspan="2">AUH</td><td>Cl<sup>-</sup>/H<sup>+</sup> = 31.1 (-)<sup>[a]</sup></td><td>9(-)<sup>[a]</sup></td></tr><tr><td>Cl<sup>-</sup>/H<sup>+</sup> = 17.8 (+)<sup>[b]</sup></td><td>44(+)<sup>[b]</sup></td></tr><tr><td>C7UH</td><td>Cl<sup>-</sup>/H<sup>+</sup> = 15.5</td><td>6</td></tr><tr><td>C8UH</td><td>Cl<sup>-</sup>/H<sup>+</sup> = 71</td><td>8</td></tr></tbody></table>

[a] Under negative voltage shock (-); [b] Under positive voltage shock (+).

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Manuscript received: July 22, 2024

Accepted manuscript online: September 20, 2024

Version of record online: October 31, 2024