Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A deep cavitand with a fluorescent wall functions as an ion sensor.

ABSTRACT: The synthesis and characterization of a deep cavitand bearing a fluorescent benzoquinoxaline wall is reported. Noncovalent host-guest recognition events are exploited to sense small charged molecules including acetylcholine. The cavitand also exhibits an anion dependent change in fluorescence that is used to differentiate halide ions in solution.

SUBMITTER: Berryman OB

PROVIDER: S-EPMC3186209 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A deep cavitand with a fluorescent wall functions as an ion sensor.

Berryman Orion B OB Sather Aaron C AC Rebek Julius J

Organic letters 20110913 19

The synthesis and characterization of a deep cavitand bearing a fluorescent benzoquinoxaline wall is reported. Noncovalent host-guest recognition events are exploited to sense small charged molecules including acetylcholine. The cavitand also exhibits an anion dependent change in fluorescence that is used to differentiate halide ions in solution. ...[more]

PMID: 21913699

Similar Datasets

A light controlled cavitand wall regulates guest binding.

Project description:Here we report a cavitand with a photochemical switch as one of the container walls. The azo-arene switch undergoes photoisomerization when subjected to UV light producing a self-fulfilled cavitand. This process is thermally and photochemically reversible. The reported cavitand binds small molecules and these guests can be ejected from the cavitand through this photochemical process.

| S-EPMC3010387 | biostudies-literature

Guest recognition in a partially bridged deep cavitand.

Project description:The synthesis of a new deep cavitand partially bridged via disulfide bonds is described. Its thermodynamic and kinetic complexation parameters are compared with those of an unbridged analogue. The disulfide bridges cause deviations in ?H and ?S but result in only small differences in ?G of complexation. The bridges increase the activation barrier for guest dissociation and lead to complexes with enhanced kinetic stability.

| S-EPMC2966534 | biostudies-literature

A highly selective "turn-on" water-soluble fluorescent sensor for gallium ion detection.

Project description:In this work, a novel sensor, (E)-N'-(3-(tert-butyl)-2-hydroxybenzylidene)thiophene-2-carbohydrazide (1), based on salicylaldehyde and thiophene hydrazide moieties was designed and synthesized. The single-crystal structure of 1 was achieved and studied for understanding its functional properties. The interaction and recognition abilities of 1 with different metal ions were investigated. Sensor 1 showed excellent "turn-on" fluorescence with highly selective and specific recognition ability in the presence of gallium ions (Ga3+) in an aqueous solution. The sensing behavior of 1 with Ga3+ was also studied by photophysical experiments, ESI-MS analysis, and 1H NMR titration. The limit of detection (LOD) and limit of quantification (LOQ) of 1 for the detection of Ga3+ in an aqueous solution were calculated as 58 nM, and 192 nM, respectively. DFT calculations were carried out to optimize the configuration of 1 and 1-Ga3+ complexes and rationalize the photophysical experimental data. Highly selective test strips based on sensor 1 were developed for Ga3+ detection. Sensor 1 was also used to detect Ga3+ in actual water samples, and a considerable recovery rate was obtained.

| S-EPMC9033676 | biostudies-literature

Deep Cavitand Calixarene-Solubilized Fullerene as a Potential Photodynamic Agent.

Project description:Fullerene has attracted much attention in biomedical research due to its unique physical and chemical properties. However, the hydrophobic nature of fullerene is limited to deploy in the body, given that the biofluids are mainly water. In this study, a water-soluble supramolecular nanoformulation based on a deep cavitand calixarene (SAC4A) and fullerene is developed to overcome the hydrophobicity of fullerene and is used as a potential photodynamic agent. SAC4A solubilizes fullerene very well with a simple grinding method. The significantly increased water solubility of fullerene enables efficient activation of reactive oxygen species. The host-guest strategy to solubilize fullerene can not only provide a new method to achieve water solubility but also expand the biomedical applications of fullerene.

| S-EPMC8327297 | biostudies-literature

Sensing of citrulline modifications in histone peptides by deep cavitand hosts.

Project description:Arrayed cavitand:fluorophore sensor complexes can selectively sense small citrulline modifications at arginine residues on post-translationally modified peptides. The sensor can differentiate between different numbers of citrulline modifications, and a simple two-fluorophore, 6-component array can effect cross-reactive discrimination between single modifications in aqueous solution.

| S-EPMC6872487 | biostudies-literature

A new, deep quinoxaline-based cavitand receptor for the complexation of benzene.

Project description:We report the synthesis of a new macrocyclic receptor, namely 2,8,14,20-tetra-hexyl-4,24:6,10:12,16:18,22-O,O'-tetra-kis-[2,3-di-hydro-[1,4]dioxino[2,3-g]quinoxalin-7,8-di-yl]resorcin[4]arene, DeepQxCav, obtained by the addition of ethyl-ene glycol di-tosyl-ate to an octa-hydroxy quinoxaline cavitand. A 1:1 supra-molecular complex of this cavitand with benzene has been obtained and analysed through X-ray diffraction analysis. The complex, of general formula C92H88O16N8·C6H6, crystallizes in the space group C2/c, with the cavitand host located about a twofold rotation axis. The benzene guest, which is held inside the cavity by C-H?? inter-actions and dispersion forces, is disordered over two equivalent sites, one in a general position and one lying on a twofold axis. The crystal structure features C-H?O hydrogen bonds and C-H?? inter-actions involving the alkyl chains, the aromatic rings, and the O atoms of the dioxane moiety of the resorcinarene scaffold. The crystal studied was refined as a two-component twin.

| S-EPMC6362646 | biostudies-literature

Spontaneous drying of non-polar deep-cavity cavitand pockets in aqueous solution.

Project description:There are many open questions regarding the hydration of solvent-exposed non-polar tracts and pockets in proteins. Although water is predicted to de-wet purely repulsive surfaces and evacuate crevices, the extent of de-wetting is unclear when ubiquitous van der Waals interactions are in play. The structural simplicity of synthetic supramolecular hosts imbues them with considerable potential to address this issue. To this end, here we detail a combination of densimetry and molecular dynamics simulations of three cavitands, coupled with calorimetric studies of their complexes with short-chain carboxylates. Our results reveal the range of wettability possible within the ostensibly identical cavitand pockets-which differ only in the presence and/or position of the methyl groups that encircle the portal to their non-polar pockets. The results demonstrate the ability of macrocycles to template water cavitation within their binding sites and show how the orientation of methyl groups can trigger the drying of non-polar pockets in liquid water, which suggests new avenues to control guest complexation.

| S-EPMC8170693 | biostudies-literature

Excited-state structural dynamics of a dual-emission calmodulin-green fluorescent protein sensor for calcium ion imaging.

Project description:Fluorescent proteins (FPs) have played a pivotal role in bioimaging and advancing biomedicine. The versatile fluorescence from engineered, genetically encodable FP variants greatly enhances cellular imaging capabilities, which are dictated by excited-state structural dynamics of the embedded chromophore inside the protein pocket. Visualization of the molecular choreography of the photoexcited chromophore requires a spectroscopic technique capable of resolving atomic motions on the intrinsic timescale of femtosecond to picosecond. We use femtosecond stimulated Raman spectroscopy to study the excited-state conformational dynamics of a recently developed FP-calmodulin biosensor, GEM-GECO1, for calcium ion (Ca(2+)) sensing. This study reveals that, in the absence of Ca(2+), the dominant skeletal motion is a ? 170 cm(-1) phenol-ring in-plane rocking that facilitates excited-state proton transfer (ESPT) with a time constant of ? 30 ps (6 times slower than wild-type GFP) to reach the green fluorescent state. The functional relevance of the motion is corroborated by molecular dynamics simulations. Upon Ca(2+) binding, this in-plane rocking motion diminishes, and blue emission from a trapped photoexcited neutral chromophore dominates because ESPT is inhibited. Fluorescence properties of site-specific protein mutants lend further support to functional roles of key residues including proline 377 in modulating the H-bonding network and fluorescence outcome. These crucial structural dynamics insights will aid rational design in bioengineering to generate versatile, robust, and more sensitive optical sensors to detect Ca(2+) in physiologically relevant environments.

| S-EPMC4104898 | biostudies-literature

A Simple Turn-off Schiff Base Fluorescent Sensor for Copper (II) Ion and Its Application in Water Analysis.

Project description:An aniline-functionalized naphthalene dialdehyde Schiff base fluorescent probe L with aggregation-induced enhanced emission (AIEE) characteristics was synthesized via a simple one-step condensation reaction and exhibited excellent sensitivity and selectivity towards copper(II) ions in aqueous media with a fluorescence " turn-off " phenomenon. The detection limit of the probe is 1.64 × 10-8 mol·L-1. Furthermore, according to the results of the UV-vis/fluorescence titrations, Job's plot method and 1H-NMR titrations, a 1:2 stoichiometry was identified. The binding constant between L and Cu2+ was calculated to be Ka = 1.222 × 103. In addition, the AIEE fluorescent probe L could be applied to detection in real water samples with satisfactory recoveries in the range 99.10-102.90% in lake water and 98.49-102.37% in tap water.

| S-EPMC7956479 | biostudies-literature

Tris-(2-aminoethyl)amine-Intercalated Graphene Oxide as an Efficient 2D Material for Cerium-Ion Fluorescent Sensor Applications.

Project description:In this work, we report the covalent functionalization of tris(2-aminoethyl)amine (tren) onto the graphene oxide surface by the ring opening of epoxide with primary amine moieties. The effect of intercalation creates the covalent coordinating moieties in between the basal planes of graphene oxide by increasing the interlayer spacing of 1.08 nm from 0.75 nm and thereby decreasing 2θ of 8.17 deg from 10.46 deg. Because of the intercalation of tren, the aminoalcohol moieties are formed in the GO planes and the intercalated material is characterized by the spectroscopic (IR, XPS, UV, and Fluorescence) and microscopic techniques. The DFT calculation shows the newly formed C-N bond length of 1.484 Å and enhanced energy gap due to functionalization. The intercalated material shows a good selective fluorescent chemosensor for the cerium ion in aqueous solution. The reversibility and its interference with other competing metal ions have been studied. The enhanced fluorescence upon the addition of cerium ions is due to the intramolecular charge transfer and photoinduced electron transfer processes in the sp2- and sp3-hybridized carbon networks.

| S-EPMC6941174 | 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