A series of triazole–cyanostilbene
receptors were designed
and synthesized. The receptor binds with the anions through various
CH···anion hydrogen bonding interactions, where strong
binding was observed for SO4
2– anions
followed by Cl–, Br–, NO3
–, and I–, calculated from the 1H NMR titration experiment. The NOESY NMR experiment of the
receptor confirmed the formation of anion-induced folded conformation.
The CH···anion hydrogen bonding interaction-mediated
anion recognition and foldamer formation were further confirmed from
geometry optimization studies of the anion-bound complex. The receptor
transports Cl– anions efficiently compared to SO4
2– anions across the lipid bilayer membrane
via a mobile carrier mechanism.
Photoswitchable acylhydrazone-based synthetic anionophores are reported. Single-crystal X-ray structure and 1 H NMR titration studies confirmed the chloride binding in solid and solution states. The ion transport activity of 1a was greatly attenuated through a phototriggered E to Z photoisomerization process, and the photoisomerized deactivated state showed high kinetic stability due to an intramolecular hydrogen bond. Switchable "OFF−ON" transport activity was achieved by the application of light and acid-catalyzed reactivation process.
Achieving superfast water transport by synthetically designed molecular artifacts, which exclude salts and protons, is a challenging task in separation science today, as it requires the concomitant presence of a...
Phenylhydrazone‐based synthetic receptors are reported as stimuli‐responsive anion transporters. The X‐ray crystallographic studies confirmed the preorganized anion binding E‐state and closed non‐binding Z‐state. The detailed ion transport mechanistic studies confirmed Cl−/anion exchange as the primary ion transport process. Their light‐stimulated E‐to‐Z isomerization led to a substantial decrease in the ion transport activity across the lipid bilayer membrane. Reversible “OFF” and “ON” activity switching was studied by light and acid stimuli, respectively.
The majority of cellular physiological processes depend on natural ion channels, which are pore-forming membrane-embedded proteins that let ions flow across the cell membranes selectively. This selective movement of ions...
Stimulus-responsive reversible transformation between two structural conformers is an essential process in many biological systems. An example of such a process is the conversion of amyloid-β peptide into β-sheet-rich oligomers, which leads to the accumulation of insoluble amyloid in the brain, in Alzheimer’s disease. To reverse this unique structural shift and prevent amyloid accumulation, β-sheet breakers are used. Herein, we report a series of bis(indole)-based biofunctional molecules, which form a stable double helix structure in the solid and solution state. In presence of chloride anion, the double helical structure unwinds to form an anion-coordinated supramolecular polymeric channel, which in turn rewinds upon the addition of Ag+ salts. Moreover, the formation of the anion-induced supramolecular ion channel results in efficient ion transport across lipid bilayer membranes with excellent chloride selectivity. This work demonstrates anion-cation-assisted stimulus-responsive unwinding and rewinding of artificial double-helix systems, paving way for smart materials with better biomedical applications.
Synthetic
anion transmembrane transporters are adding new aspirations
for treating channelopathies by replacing defective ion channels.
The availability of such suitable candidates is still infrequent due
to the associated toxicity. Here, we report 3-(1H-1,2,3-triazol-1-yl)benzamides as transmembrane anion carriers, nontoxic
to cells. The selective and electrogenic chloride transport activity
was established by fluorescence and ion selective electrode-based
assays. MQAE assay confirmed the chloride uptake into the cells by
the nontoxic compounds.
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