anion recognition
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2022 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale

Understanding non-covalent molecular recognition events at biomembrane interfaces is important in biological, medicinal, and materials chemistry research.1 Despite the crucial regulatory roles of anion binding/transport processes at biomembranes, no information is available regarding how strongly anions can bind to naturally occurring or synthetic receptors in lipid bilayer environments compared to their well-established behaviour in solutions.2 To bridge this knowledge gap, we synthesised a flat macrocycle that possesses a record aqueous SO42– affinity among neutral receptors and exploited its unique fluorescence response at interfaces. We show that the determinants of anion binding are extraordinarily different in organic solvents and in lipid bilayers. The high charge density of dihydrogen phosphate and chloride ions prevails in DMSO, however in lipids they fail to bind the macrocycle. Perchlorate and iodide hardly bind in DMSO but show significant affinities for the macrocycle in lipids. Our results demonstrate a surprisingly great advantage of large, charge-diffuse anions to bind to a lipid-embedded synthetic receptor mainly attributed to their higher polarisabilities and deeper penetration into the bilayer, beyond the common knowledge of dehydration energy-governed selectivity. The elucidation of these principles enhances our understanding of biological anion recognition functions in membranes and guides the design of ionophores and molecular machines operating at biomembrane interfaces.


2021 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale

Understanding non-covalent molecular recognition events at biomembrane interfaces is important in biological, medicinal, and materials chemistry research.1 Despite the crucial regulatory roles of anion binding/transport processes at biomembranes, no information is available regarding how strongly anions can bind to naturally occurring or synthetic receptors in lipid bilayer environments compared to their well-established behaviour in solutions.2 To bridge this knowledge gap, we synthesised a flat macrocycle that possesses a record aqueous SO42– affinity among neutral receptors and exploited its unique fluorescence response at interfaces. We show that the determinants of anion binding are extraordinarily different in organic solvents and in lipid bilayers. The high charge density of dihydrogen phosphate and chloride ions prevails in DMSO, however in lipids they fail to bind the macrocycle. Perchlorate and iodide hardly bind in DMSO but show significant affinities for the macrocycle in lipids. Our results demonstrate a surprisingly great advantage of large, charge-diffuse anions to bind to a lipid-embedded synthetic receptor mainly attributed to their higher polarisabilities and deeper penetration into the bilayer, beyond the common knowledge of dehydration energy-governed selectivity. The elucidation of these principles enhances our understanding of biological anion recognition functions in membranes and guides the design of ionophores and molecular machines operating at biomembrane interfaces.


2021 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale

Understanding non-covalent molecular recognition events at biomembrane interfaces is important in biological, medicinal, and materials chemistry research.1 Despite the crucial regulatory roles of anion binding/transport processes at biomembranes, no information is available regarding how strongly anions can bind to naturally occurring or synthetic receptors in lipid bilayer environments compared to their well-established behaviour in solutions.2 To bridge this knowledge gap, we synthesised a flat macrocycle that possesses a record aqueous SO42– affinity among neutral receptors and exploited its unique fluorescence response at interfaces. We show that the determinants of anion binding are extraordinarily different in organic solvents and in lipid bilayers. The high charge density of dihydrogen phosphate and chloride ions prevails in DMSO, however in lipids they fail to bind the macrocycle. Perchlorate and iodide hardly bind in DMSO but show significant affinities for the macrocycle in lipids. Our results demonstrate a surprisingly great advantage of large, charge-diffuse anions to bind to a lipid-embedded synthetic receptor mainly attributed to their higher polarisabilities and deeper penetration into the bilayer, beyond the common knowledge of dehydration energy-governed selectivity. The elucidation of these principles enhances our understanding of biological anion recognition functions in membranes and guides the design of ionophores and molecular machines operating at biomembrane interfaces.


2021 ◽  
Vol 449 ◽  
pp. 214206
Author(s):  
Adam F. Henwood ◽  
Isabel N. Hegarty ◽  
Eoin P. McCarney ◽  
June I. Lovitt ◽  
Shauna Donohoe ◽  
...  

2021 ◽  
pp. 79-109
Author(s):  
Edward G. Sheetz ◽  
David Van Craen ◽  
Amar H. Flood

2021 ◽  
pp. 1-77
Author(s):  
Friedemann Dressler ◽  
Peter R. Schreiner

Polyhedron ◽  
2021 ◽  
Vol 209 ◽  
pp. 115482
Author(s):  
Thanthapatra Bunchuay ◽  
Andrew Docker ◽  
Nicholas G. White ◽  
Paul D. Beer

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6417
Author(s):  
Patryk Niedbała ◽  
Kajetan Dąbrowa ◽  
Sylwia Wasiłek ◽  
Janusz Jurczak

Recognition of anionic species plays a fundamental role in many essential chemical, biological, and environmental processes. Numerous monographs and review papers on molecular recognition of anions by synthetic receptors reflect the continuing and growing interest in this area of supramolecular chemistry. However, despite the enormous progress made over the last 20 years in the design of these molecules, the design of receptors for chiral anions is much less developed. Chiral recognition is one of the most subtle types of selectivity, and it requires very precise spatial organization of the receptor framework. At the same time, this phenomenon commonly occurs in many processes present in nature, often being their fundamental step. For these reasons, research directed toward understanding the chiral anion recognition phenomenon may lead to the identification of structural patterns that enable increasingly efficient receptor design. In this review, we present the recent progress made in the area of synthetic receptors for biologically relevant chiral carboxylates.


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