Calix[6]arenes with halogen bond donor groups as selective and efficient anion transporters

Singh, Anurag; Torres-Huerta, Aarón; Vanderlinden, Tom; Renier, Nathan; Martínez‐Crespo, Luis; Tumanov, Nikolay; Bartik, Kristin; Jabin, Ivan; Valkenier, Hennie

doi:10.1039/d2cc00847e

Cited by 27 publications

(29 citation statements)

References 33 publications

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“…[1][2][3] Toxic side effects are expected to be minimised by using anionophores with high selectivity for targeted anions. 4,5 On the other hand, H + Cl − symporters show promise as candidates for anti-cancer agents. [6][7][8] Chloride transporters have been also shown to display promising antibacterial activity, notably against antibiotic resistant bacteria.…”

Section: Introductionmentioning

confidence: 99%

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

et al. 2022

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“…While these two compounds performed Cl − /NO3 − antiport with similar activities, 39 is an inactive Cl − /HCO3 − antiport agent under the conditions used to obtain efficient transport by 20. 65 It should be noted that most of these transporters with remarkable selectivity for Cl − /NO3 − antiport have no acidic NH or OH groups. We suggest that the poor response obtained for these compounds in Cl − /HCO3 − antiport assays might be related to their inability to perform H + Cl − symport, a process that can lead to neat Cl − /HCO3 − antiport, as discussed in Section 4.2.…”

Section: Anion Transport Selectivitymentioning

confidence: 99%

“…Only in a recent study, Valkenier and coworkers have described tris-squaramide 20, based on a calix[6]arene scaffold, as an efficient chloride and bicarbonate transporter. 65 Phthalamides 3a-c and ceramide 6 are early examples of amide-based bicarbonate transporters. While the former contain two amide groups pre-organized by an aryl scaffold to bind the same anion, the later combines one amide and two alcohol groups as anion binding units.…”

Section: Neutral Transporters With Acidic Nh 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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“…1,2 Toxic side effects are expected to be minimised by using anionophores with high selectivity for targeted anions. 3,4 On the other hand, H + Cl − symporters show promise as candidates for anti-cancer agents. 5,6,7 Chloride transporters have been also shown to display promising antibacterial activity, notably against antibiotic resistant bacteria.…”

Section: Introductionmentioning

confidence: 99%

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

Maslowska-Jarzyna

Cataldo

Marszalik

et al. 2022

Preprint

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Synthetic ionophores able to transport bicarbonate and chloride anions across lipid bilayers are appealing for their wide range of potential biological applications. We have studied the bicarbonate and chloride transport by carbazoles with two amido/thioamido groups using a bicarbonate-sensitive europium(III) probe in liposomes and found a highly remarkable concentration dependence. This can be explained by a combination of two distinct transport mechanisms: HCO3−/Cl− exchange and a combination of unassisted CO2 diffusion and HCl transport, of which the respective contributions were quantified. The compounds studied were found to be highly potent HCl transporters. Based on the mechanistic insights on anion transport, we have tested the antimicrobial activity of these compounds and found good correlation with their ion transport properties and a high activity against Gram-positive bacteria.

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Calix[6]arenes with halogen bond donor groups as selective and efficient anion transporters

Abstract: A calix[6]arene with three preorganised halogen bond donating groups gives >100-fold selectivity for Cl− uniport over HCl symport, in contrast to analogous compounds with strong hydrogen bond donating groups.

Cited by 27 publications

References 33 publications

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

Transmembrane transport of bicarbonate by anion receptors

Dissecting transmembrane bicarbonate transport by 1,8-di(thio)amidocarbazoles

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