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Recognition of Hydrophilic Cyclic Compounds by a Water-Soluble Cavitand.

ABSTRACT: A water-soluble deep cavitand bearing amides on the upper rim and trimethyl ammonium groups on the feet was synthesized. The open-ended cavity is stabilized by the intramolecular hydrogen bonds formed between the adjacent amides, and the introduction of trimethylammonium imparts to the cavitand good solubility in water. The cavitand exhibits high binding affinity and selectivity to hydrophilic molecules in water. With certain guests, such as cyclohexyl alcohols, amines and acids, the recognition involves the synergistic action of hydrogen bonding with hydrophobic effects. The binding phenomena are interpreted in terms of a fixed solvent cage presented by the host to the guest.

SUBMITTER: Wan YH

PROVIDER: S-EPMC8037811 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Origin of the blueshift of water molecules at interfaces of hydrophilic cyclic compounds.

Project description:Water molecules at interfaces of materials exhibit enigmatic properties. A variety of spectroscopic studies have observed a high-frequency motion in these water molecules, represented by a blueshift, at both hydrophobic and hydrophilic interfaces. However, the molecular mechanism behind this blueshift has remained unclear. Using Raman spectroscopy and ab initio molecular dynamics simulations, we reveal the molecular mechanism of the blueshift of water molecules around six monosaccharide isomers. In the first hydration shell, we found weak hydrogen-bonded water molecules that cannot have a stable tetrahedral water network. In the water molecules, the vibrational state of the OH bond oriented toward the bulk solvent strongly contributes to the observed blueshift. Our work suggests that the blueshift in various solutions originates from the vibrational motions of these observed water molecules.

| S-EPMC5741398 | biostudies-literature

Cavitand-Decorated Silicon Columnar Nanostructures for the Surface Recognition of Volatile Nitroaromatic Compounds.

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| S-EPMC6644403 | biostudies-literature

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| S-EPMC3289311 | biostudies-literature

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| S-EPMC2966534 | biostudies-literature

Ultrasound-assisted synthesis of water-soluble monosubstituted diruthenium compounds.

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| S-EPMC8605285 | biostudies-literature

ITC and NMR Analysis of the Encapsulation of Fatty Acids within a Water-Soluble Cavitand and its Dimeric Capsule.

Project description:We report here NMR and ITC studies of the binding of ionizable guests (carboxylate acids) to a deep-cavity cavitand. These studies reveal that the shortest guests favored 1:1 complex formation, but the longer the alkyl chain the more the 2:1 host-guest capsule is favored. For intermediate-sized guests, the equilibrium between these two states is controlled by pH; at low values the capsule containing the carboxylic acid guest is favored, whereas as the pH is raised deprotonation of the guest favors the 1:1 complex. Interestingly, for one host-guest pair the energy required to de-cap the 2:1 capsular complex and form the 1:1 complex is sufficient to shift the pKa of the guest by ~ 3-4 orders of magnitude (4.1-5.4 kcal mol-1). The two largest guests examined form stable 2:1 capsules, with in both cases the guest adopting a relatively high energy J-shaped motif. Furthermore, these 2:1 complexes are sufficiently stable that at high pH guest deprotonation occurs without de-capping of the capsule.

| S-EPMC4792523 | biostudies-literature

Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand.

Project description:We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diastereomeric host-guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced-fit behavior with regards to resorcin[4]arene derived self-folding cavitands.

| S-EPMC10186369 | biostudies-literature

A Newly Designed Water Soluble Uranyl-Salophen Complex for Anion Recognition.

Project description:A novel water-soluble uranyl-salophen (salophen=N,N'-disalicylidene-o-phenylenediaminate) complex was obtained. Solubility was achieved in aqueous methyl-β-cyclodextrin solutions, taking advantage of the host-guest interactions established with the adamantyl moieties present on the ligand skeleton. Such an approach facilitates the synthesis of the receptor and the purification processes and, in perspective, can be definitely applicable to other molecular scaffolds. UV/Vis titration experiments demonstrate that the capacity of the uranyl-salophen core to behave as a receptor for anions is retained in water and appears comparable with that previously reported for other water-soluble uranyl-salophen systems. Hence the presence of cyclodextrins does not interfere with molecular recognition processes.

| S-EPMC8385332 | biostudies-literature

Molecular Recognition in an Aqueous Medium Using Water-Soluble Prismarene Hosts.

Project description:The synthesis of water-soluble prism[n]arenes (n = 5 and 6) bearing anionic carboxylato groups on the rims is described. The binding properties of this novel class of water-soluble hosts are studied by nuclear magnetic resonance and calorimetry. The complexation of singly and doubly charged ammonium guests with the more rigid pentamer is enthalpically driven by secondary interactions, while the thermodynamic fingerprint for the larger hexamer reveals driving forces that strongly depend on the guest charge and/or size.

| S-EPMC9016763 | biostudies-literature

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