Conformational Control of a Pyrrole-Based Amide Pentamer by Dihydrogen Phosphate Anion Binding

Heterocycles ◽  
2019 ◽  
Vol 98 (4) ◽  
pp. 551
Author(s):  
Quan Gan ◽  
Guoping Li ◽  
Jiulong Li ◽  
Chaocao Lu ◽  
Bu Htan ◽  
...  
Keyword(s):  
Anion Binding ◽  
Dihydrogen Phosphate ◽  
Phosphate Anion ◽  
Conformational Control

scholarly journals Measuring anion binding at biomembrane interfaces

2021 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale
Keyword(s):  
Lipid Bilayers ◽  
Common Knowledge ◽  
Anion Recognition ◽  
Chloride Ions ◽  
Transport Processes ◽  
Anion Binding ◽  
Dihydrogen Phosphate ◽  
Materials Chemistry ◽  
Synthetic Receptor ◽  
Chemistry Research

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.

Conformational control by ‘zipping-up’ an anion-binding unimolecular capsule

2008 ◽  
pp. 1395 ◽  
Author(s):  
David R. Turner ◽  
Martin J. Paterson ◽  
Jonathan W. Steed
Keyword(s):  
Anion Binding ◽  
Conformational Control

scholarly journals Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1807 ◽  
Author(s):  
Alena Khadieva ◽  
Vladimir Gorbachuk ◽  
Dmitriy Shurpik ◽  
Ivan Stoikov
Keyword(s):  
Hydrogen Bond ◽  
1H Nmr Spectroscopy ◽  
Color Change ◽  
Amide Group ◽  
Anion Binding ◽  
Dihydrogen Phosphate ◽  
Imino Group ◽  
Colorimetric Probe ◽  
Arene Complex ◽  
Phosphate Anions

A multicyclophane with a core based on tris(2-aminoethyl)amine (TREN) linked by amide spacers to three fragments of pillar[5]arene was synthesized. The choice of the tris-amide core allowed the multicyclophane to bind to anion guests. The presence of three terminal pillar[5]arene units provides the possibility of effectively binding the colorimetric probe N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine (PhTz). It was established that the multicyclophane complexed PhTz in chloroform with a 1:1 stoichiometry (lgKa = 5.2 ± 0.1), absorbing at 650 nm. The proposed structure of the complex was confirmed by 1H-NMR spectroscopy: the amide group linking the pillar[5]arene to the TREN core forms a hydrogen bond with the PhTz imino-group while the pillararenes surround PhTz. It was established that the PhTz:tris-pillar[5]arene complex could be used as a colorimetric probe for fluoride, acetate, and dihydrogen phosphate anions due to the anion binding with proton donating amide groups which displaced the PhTz probe. Dye displacement resulted in a color change from blue to pink, lowering the absorption band at 650 nm and increasing that at 533 nm.

Calix[4]arene based neutral receptor for dihydrogen phosphate anion

Tetrahedron ◽  
2008 ◽  
Vol 64 (4) ◽  
pp. 741-748 ◽  
Author(s):  
Har Mohindra Chawla ◽  
Suneel Pratap Singh
Keyword(s):  
Dihydrogen Phosphate ◽  
Phosphate Anion

Anion Coordination of Bis-bisurea Ligands: Aggregation of Dihydrogen Phosphate Anion into Oligomers and Infinite Chains

2015 ◽  
Vol 641 (10) ◽  
pp. 1786-1791 ◽  
Author(s):  
Biao Wu ◽  
Cuirong Huo ◽  
Shaoguang Li ◽  
Yanxia Zhao ◽  
Xiao-Juan Yang
Keyword(s):  
Dihydrogen Phosphate ◽  
Phosphate Anion ◽  
Anion Coordination

scholarly journals Measuring anion binding at biomembrane interfaces

2022 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale
Keyword(s):  
Lipid Bilayers ◽  
Common Knowledge ◽  
Anion Recognition ◽  
Chloride Ions ◽  
Transport Processes ◽  
Anion Binding ◽  
Dihydrogen Phosphate ◽  
Materials Chemistry ◽  
Synthetic Receptor ◽  
Chemistry Research

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.

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