Synthetic chloride transporters with the binding mode observed in a ClC chloride channel

Choi, Ye Rin; Chae, Min Kyung; Kim, Dong-Wook; Lah, Myoung Soo; Jeong, Kyu Sung

doi:10.1039/c2cc35743g

Cited by 23 publications

(21 citation statements)

References 55 publications

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“…The Jeong group was successfully able to design a synthetic chloride channel to mimic the S. typhimurium protein. [92] The combination of four hydrogen-bond donors in an anion-binding pocket with judicious side-chain selection produced a potent anion binder and anion transporter. The presence of both a greasy side-chain and activated alcohols was necessary for efficient anion transport.…”

Section: Emerging Areasmentioning

confidence: 99%

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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The aryl–ethynyl linkage has been extensively employed in the construction of hosts for a variety of guests. Uses range from ion detection (e.g., of metal cations in the environment or industrial waste and of anions prevalent in nature), to molecular mimics for biological systems, and to applications targeting future safety issues (such as CO2 capture and indicators for the manufacture of chemical weapons). This Focus Review examines the utilization of the aryl–ethynyl linkage in engineering host molecules for a variety of different guests, and how the alkyne unit plays an integral part as both a rigid scaffolding section in host geometry design as well as a linker to allow conjugative communication between discrete π-electron systems.

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Section: Emerging Areasmentioning

confidence: 99%

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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“…Nearly all O−H containing anion receptors have been neutral and have functioned in organic solvents, or in rare cases organic solvents containing 1 % water . In an effort to move towards systems that can function in water, in this work we prepare the cationic hydroxy‐containing anion host systems 1 + and 2 + (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Easily‐prepared Hydroxy‐containing Receptors Recognize Anions in Aqueous Media

Morshedi

Boer

Thomas

et al. 2019

Chemistry An Asian Journal

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Despite their ready availability, O−H groups have received relatively little attention as anion recognition motifs. Here, we report two simple hydroxy‐containing anion receptors that are prepared in two facile steps followed by anion exchange, without the need for chromatographic purification at any stage. These receptors contain a pyridinium bis(amide) motif as well as hydroxyphenyl groups, and bind mono‐ and divalent anions in 9:1 CD3CN:D2O, showing a selectivity preference for sulfate. Notably, a “model” receptor that does not contain hydroxy groups shows only very weak sulfate binding in this competitive solvent mixture. In the solid state, X‐ray crystallographic studies show that the receptors tend to form extended assemblies with anions; however, 1H and DOSY NMR studies as well as molecular dynamics simulations show that only 1:1 complexes are present in solution. Molecular dynamics simulations suggest that one of the receptors suffers from competing intramolecular hydrogen bonding, while another binds partially‐hydrated anions, with the receptor's O−H groups forming hydrogen bonds to water molecules within the anion's coordination sphere.

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“…We found ISMs fabricated with these compounds had one or more of the following problems: lack of linearity, sub- or supra-Nernstian responses, drift, hysteresis, poor solubility in liquid membranes, sensitivity to blockers of chloride channels or transporters, and poor selectivity for Cl − over . We also tested a chemically diverse group of recently published compounds described as Cl − carriers for biological membranes: compound-1 18 , compound 4H 19 , cholapod-3, and decalin-13 16,20,21 , and found them not appropriate to build ISMs, mostly demonstrating solubility problems.…”

Section: Introductionmentioning

confidence: 99%

A highly-selective chloride microelectrode based on a mercuracarborand anion carrier

DiFranco

Quiñonez

Dziedzic

et al. 2019

Sci Rep

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The chloride gradient plays an important role in regulating cell volume, membrane potential, pH, secretion, and the reversal potential of inhibitory glycine and GABAA receptors. Measurement of intracellular chloride activity, , using liquid membrane ion-selective microelectrodes (ISM), however, has been limited by the physiochemical properties of Cl− ionophores which have caused poor stability, drift, sluggish response times, and interference from other biologically relevant anions. Most importantly, intracellular may be up to 4 times more abundant than Cl− (e.g. skeletal muscle) which places severe constraints on the required selectivity of a Cl− – sensing ISM. Previously, a sensitive and highly-selective Cl− sensor was developed in a polymeric membrane electrode using a trinuclear Hg(II) complex containing carborane-based ligands, [9]-mercuracarborand-3, or MC3 for short. Here, we have adapted the use of the MC3 anion carrier in a liquid membrane ion-selective microelectrode and show the MC3-ISM has a linear Nernstian response over a wide range of aCl (0.1 mM to 100 mM), is highly selective for Cl− over other biological anions or inhibitors of Cl− transport, and has a 10% to 90% settling time of 3 sec. Importantly, over the physiological range of aCl (1 mM to 100 mM) the potentiometric response of the MC3-ISM is insensitive to or changes in pH. Finally, we demonstrate the biological application of an MC3-ISM by measuring intracellular aCl, and the response to an external Cl-free challenge, for an isolated skeletal muscle fiber.

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Synthetic chloride transporters with the binding mode observed in a ClC chloride channel

Abstract: A series of synthetic molecules bearing the same hydrogen bonding mode observed in StClC were prepared and their transport ability of chloride ion across a lipid membrane was systematically optimized.

Cited by 23 publications

References 55 publications

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Easily‐prepared Hydroxy‐containing Receptors Recognize Anions in Aqueous Media

A highly-selective chloride microelectrode based on a mercuracarborand anion carrier

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