Browse
Submit Data
Databases
API
Help

Dataset Information

31 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

PH-Responsive Host-Guest Complexations Between a Water-Soluble Pillar[6]arene Dodecyl-Ammonium Chloride and Aromatic Sulfonic Acids.

ABSTRACT: In the present work, new host-guest binding motifs based on a water-soluble pillar[6]arene dodecyl-ammonium chloride (CP6) with two aromatic sulfonic acids in aqueous media were fabricated. In accordance with the integrated results of 1H NMR, 2D NOESY, and florescence titration experiments, it was demonstrated that the host-guest binding of CP6 with the two aromatic sulfonic acids in aqueous solution not only has high binding constants but also has pH-responsiveness.

SUBMITTER: Duan Q

PROVIDER: S-EPMC7533581 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

pH-Responsive Host-Guest Complexations Between a Water-Soluble Pillar[6]arene Dodecyl-Ammonium Chloride and Aromatic Sulfonic Acids.

Duan Qunpeng Q Wang Fei F Zhang Hongsong H Lu Kui K

Frontiers in chemistry 20200915

In the present work, new host-guest binding motifs based on a water-soluble pillar[6]arene dodecyl-ammonium chloride (CP6) with two aromatic sulfonic acids in aqueous media were fabricated. In accordance with the integrated results of <sup>1</sup>H NMR, 2D NOESY, and florescence titration experiments, it was demonstrated that the host-guest binding of CP6 with the two aromatic sulfonic acids in aqueous solution not only has high binding constants but also has pH-responsiveness. ...[more]

PMID: 33195089

Similar Datasets

pH-Responsive Host⁻Guest Complexation in Pillar[6]arene-Containing Polyelectrolyte Multilayer Films.

Project description:A water-soluble, anionic pillar[6]arene derivative (WP6) is applied as monomeric building block for the layer-by-layer self-assembly of thin polyelectrolyte multilayer films, and its pH-dependent host⁻guest properties are employed for the reversible binding and release of a methylviologen guest molecule. The alternating assembly of anionic WP6 and cationic diazo resin (DAR) is monitored in-situ by a dissipative quartz crystal microbalance (QCM-D). In solution, the formation of a stoichiometric inclusion complex of WP6 and cationic methylviologen (MV) as guest molecule is investigated by isothermal titration calorimetry and UV-vis spectroscopy, respectively, and attributed to electrostatic interactions as primary driving force of the host⁻guest complexation. Exposure of WP6-containing multilayers to MV solution reveals a significant decrease of the resonance frequency, confirming MV binding. Subsequent release is achieved by pH lowering, decreasing the host⁻guest interactions. The dissociation of the host⁻guest complex, release of the guest from the film, as well as full reversibility of the binding event are identified by QCM-D. In addition, UV-vis data quantify the surface coverage of the guest molecule in the film after loading and release, respectively. These findings establish the pH-responsiveness of WP6 as a novel external stimulus for the reversible guest molecule recognition in thin films.

| S-EPMC6418545 | biostudies-literature

A Water-Soluble Leggero Pillar[5]arene.

Project description:The study of aqueous-phase molecular recognition of artificial receptors is one of the frontiers in supramolecular chemistry since most biochemical processes and reactions take place in an aqueous medium and heavily rely on it. In this work, a water-soluble version of leggero pillar[5]arene bearing eight positively charged pyridinium moieties (CWP[5]L) was designed and synthesized, which exhibited good binding affinities with certain aliphatic sulfonate species in aqueous solutions. Significantly, control experiments demonstrate that the guest binding performance of CWP[5]L is superior to its counterpart water-soluble macrocyclic receptor in traditional pillararenes.

| S-EPMC9571795 | biostudies-literature

Styrene Purification by Guest-Induced Restructuring of Pillar[6]arene.

Project description:The separation of styrene (St) and ethylbenzene (EB) mixtures is important in the chemical industry. Here, we explore the St and EB adsorption selectivity of two pillar-shaped macrocyclic pillar[n]arenes (EtP5 and EtP6; n = 5 and 6). Both crystalline and amorphous EtP6 can capture St from a St-EB mixture with remarkably high selectivity. We show that EtP6 can be used to separate St from a 50:50 v/v St:EB mixture, yielding in a single adsorption cycle St with a purity of >99%. Single-crystal structures, powder X-ray diffraction patterns, and molecular simulations all suggest that this selectivity is due to a guest-induced structural change in EtP6 rather than a simple cavity/pore size effect. This restructuring means that the material "self-heals" upon each recrystallization, and St separation can be carried out over multiple cycles with no loss of performance.

| S-EPMC5360353 | biostudies-literature

Aggregation Mode, Host-Guest Chemistry in Water, and Extraction Capability of an Uncharged, Water-Soluble, Liquid Pillar[5]arene Derivative.

Project description:An uncharged, water-soluble per-ethylene-glycol pillar[5]arene derivative (1) was synthesized and its aggregation mode, host-guest chemistry in water and extraction ability was explored. Compound 1 is a liquid at room temperature; in water, limited self-aggregation occurred at high concentrations as deduced from diffusion NMR and dynamic light scattering. Compound 1 forms pseudo-rotaxane-like 1 : 1 host-guest complexes with 1,ω-di-substituted alkanes with association constants on the order of 103 -104 m-1 . Interestingly, NMR experiments showed that the guest location relative to the host ring system differs among the different complexes. In proof-of-concept experiments, compound 1 was shown to extract structurally related organic compounds from benzene into water with significant selectivity. Compound 1, which is a liquid at room temperature and has only limited interactions with its side arms, can, in principle, be regarded as a complement to or as a kind of type I porous liquid.

| S-EPMC8564886 | biostudies-literature

A Supramolecular Photosensitizer System Based on Nano-Cu/ZIF-8 Capped with Water-Soluble Pillar[6]arene and Methylene Blue Host-Guest Complexations.

Project description:Photodynamic therapy (PDT) as a safe, non-invasive modality for cancer therapy, in which the low oxygen and high glutathione in the tumor microenvironment reduces therapeutic efficiency. In order to overcome these problems, we prepared a supramolecular photosensitive system of O2-Cu/ZIF-8@ZIF-8@WP6-MB (OCZWM), which was loaded with oxygen to increase the oxygen concentration in the tumor microenvironment, and the Cu2+ in the system reacted with glutathione (GSH) to reduce the GSH concentration to generate Cu+. It is worth noting that the generated Cu+ can produce the Fenton reaction, thus realizing the combination therapy of PDT and chemodynamic therapy (CDT) to achieve the purpose of significantly improving the anti-cancer efficiency.

| S-EPMC8271439 | biostudies-literature

A pillar[5]arene-based covalent organic framework with pre-encoded selective host-guest recognition.

Project description:It is highly desirable to maintain both permanent accessible pores and selective molecular recognition capability of macrocyclic cavitands in the solid state. Integration of well-defined discrete macrocyclic hosts into ordered porous polymeric frameworks (e.g., covalent organic frameworks, COFs) represents a promising strategy to transform many supramolecular chemistry concepts and principles well established in the solution phase into the solid state, which can enable a broad range of practical applications, such as high-efficiency molecular separation, heterogeneous catalysis, and pollution remediation. However, it is still a challenging task to construct macrocycle-embedded COFs. In this work, a novel pillar[5]arene-derived (P5) hetero-porous COF, denoted as P5-COF, was rationally designed and synthesized. Featuring the unique backbone structure, P5-COF exhibited selective adsorption of C2H2 over C2H4 and C2H6, as well as significantly enhanced host-guest binding interaction with paraquat, in comparison with the pillar[5]arene-free COF analog, Model-COF. The present work established a new strategy for developing COFs with customizable molecular recognition/separation properties through the bottom-up "pre-porous macrocycle to porous framework" design.

| S-EPMC8528016 | biostudies-literature

A biomimetic chiral-driven ionic gate constructed by pillar[6]arene-based host-guest systems.

Project description:Inspired by glucose-sensitive ion channels, herein we describe a biomimetic glucose-enantiomer-driven ion gate via the introduction of the chiral pillar[6]arene-based host-guest systems into the artificial nanochannels. The chiral nanochannels show a high chiral-driven ionic gate for glucose enantiomers and can be switched "off" by D-glucose and be switched "on" by L-glucose. Remarkably, the chiral nanochannel also exhibited a good reversibility toward glucose enantiomers. Further research indicates that the switching behaviors differed due to the differences in binding strength between chiral pillar[6]arene and glucose enantiomers, which can lead to the different surface charge within nanochannel. Given these promising results, the studies of chiral-driven ion gates may not only give interesting insight for the research of biological and pathological processes caused by glucose-sensitive ion channels, but also help to understand the origin of the high stereoselectivity in life systems.

| S-EPMC6033921 | biostudies-literature

Tetraphenylethene-Embedded Pillar[5]arene and [15]Paracyclophane: Distorted Cavities and Host-Guest Binding Properties.

Project description:Two aggregation-induced emission (AIE) macrocycles (DMP[5]-TPE and PCP[5]-TPE) were prepared by embedding Tetraphenylethene (TPE) unit into the skeletons of Dimethoxypillar[5]arene (DMP[5]) and [15]Paracyclophane ([15]PCP) at meso position, respectively. In crystal, the PCP[5]-TPE showed a distorted cavity, and the incubation of hexane inside the DMP[5]-TPE cavity caused a distinct change in the molecular conformation compared to PCP[5]-TPE. There was no complexation between PCP[5]-TPE and 1,4-dicyanobutane (DCB). UV absorption experiments showed the distorted cavity of DMP[5]-TPE hindered association with DCB.

| S-EPMC8512412 | biostudies-literature

Cationic Pillar[6]arene Induces Cell Apoptosis by Inhibiting Protein Tyrosine Phosphorylation Via Host-Guest Recognition.

Project description:We reported for the first time that cationic pillar[6]arene (cPA6) could tightly bind to peptide polymer (MW~20-50 kDa), an artificial substrate for tyrosine (Tyr) phosphorylation, and efficiently inhibit Tyr protein phosphorylation through host-guest recognition. We synthesized a nanocomposite of black phosphorus nanosheets loaded with cPA6 (BPNS@cPA6) to explore the effect of cPA6 on cells. BPNS@cPA6 was able to enter HepG2 cells, induced apoptosis, and inhibited cell proliferation by reducing the level of Tyr phosphorylation. Furthermore, BPNS@cPA6 showed a stronger ability of inhibiting cell proliferation in tumor cells than in normal cells. Our results revealed the supramolecular modulation of enzymatic Tyr phosphorylation by the host-guest recognition of cPA6.

| S-EPMC7404071 | biostudies-literature

Enhancing the Stability and Photothermal Conversion Efficiency of ICG by Pillar[5]arene-Based Host-Guest Interaction.

Project description:Indocyanine green (ICG) is a classical near-infrared (NIR) photothermal reagent that can be employed in clinical medical detection. Under neutral conditions, ICG can adsorb NIR light effectively for photothermal (PTT) and photodynamic (PDT) therapy. However, ICG is easily degraded in weak acid environments, which seriously restricts its application. In this work, a cationic water-soluble pillar[5]arene (WP5) was selected as the stabilizing agent for ICG. Thanks to the host-guest interaction between WP5 and alkyl sulfonate, the stability and the photothermal conversion efficiency of ICG increased remarkably upon addition of WP5 as investigated by UV-vis spectrum and photothermal studies. Furthermore, an in vitro study showed higher efficiency of WP5&ICG in killing cancer cells in a shorter treatment time than the free ICG. Hence, it is hopeful that WP5 can be a new type of supramolecular host in enhancing the stability and photothermal conversion efficiency of photosensitizers.

| S-EPMC8586498 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data