Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

9-Aryl-9-xanthenols: a convenient platform for the design of fluorimetric and colorimetric pH indicators.

ABSTRACT: In aqueous and alcohol solutions, colorless and non-fluorescent derivatives of 9-aryl-9H-xanthen-9-ol equilibrate with brightly colored and fluorescent 9-arylxanthylium cations, thus offering a convenient platform for the design of dual-mode indicators for emission and absorption-based pH measurements. The position of the prototropic equilibrium depends only on the hydronium ion concentration and is not affected by general acids or other ions. Furthermore, the equilibrium equivalence point can be readily adjusted by introducing substituents in the xanthenol core. As dehydroxylation of 3,6-dialkoxy-9-(o-tolyl)-9-xanthenol occurs at pH = 6.5, indicators of this type are well suited for biological applications as illustrated by in vitro cell culture studies with NIH 3T3 cells.

SUBMITTER: Nekongo EE

PROVIDER: S-EPMC3507456 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

9-Aryl-9-xanthenols: a convenient platform for the design of fluorimetric and colorimetric pH indicators.

Nekongo Emmanuel E EE Bagchi Pritha P Fahrni Christoph J CJ Popik Vladimir V VV

Organic & biomolecular chemistry 20121029 46

In aqueous and alcohol solutions, colorless and non-fluorescent derivatives of 9-aryl-9H-xanthen-9-ol equilibrate with brightly colored and fluorescent 9-arylxanthylium cations, thus offering a convenient platform for the design of dual-mode indicators for emission and absorption-based pH measurements. The position of the prototropic equilibrium depends only on the hydronium ion concentration and is not affected by general acids or other ions. Furthermore, the equilibrium equivalence point can b ...[more]

PMID: 23104455

Similar Datasets

Selective, pH-Dependent Colorimetric and Fluorimetric Detection of Quadruplex DNA with 4-Dimethylamino(phenyl)-Substituted Berberine Derivatives.

Project description:The 9- and 12-dimethylaminophenyl-substituted berberine derivatives 3 a and 3 b were readily synthesized by Suzuki-Miyaura reactions and shown to be useful fluorescent probes for the optical detection of quadruplex DNA (G4-DNA). Their association with the nucleic acids was investigated by spectrometric titrations, CD and LD spectroscopy, and with DNA-melting analysis. Both ligands bind to duplex DNA by intercalation and to G4-DNA by terminal π stacking. At neutral conditions, they bind with higher affinity (Kb =105 -106 M-1 ) to representative quadruplex forming oligonucleotides 22AG, c-myc, c-kit, and a2, than to duplex calf thymus (ct) DNA (Kb =5-7×104 M-1 ). At pH 5, however, the affinity of 3 a towards G4-DNA 22AG is higher (Kb =1.2×106 M-1 ), whereas the binding constant towards ct DNA is lower (Kb =3.9×103 M-1 ) than under neutral conditions. Notably, the association of the ligand with DNA results in characteristic changes of the absorption and emission properties under specific conditions, which may be used for optical DNA detection. Other than the parent berberine, the ligands do not show a noticeable increase of their very low intrinsic emission intensity upon association with DNA at neutral conditions. In contrast, a fluorescence light-up effect was observed upon association to duplex (Φfl =0.01) and quadruplex DNA (Φfl =0.04) at pH 5. This fluorimetric response to G4-DNA association in combination with the distinct, red-shifted absorption under these conditions provides a simple and conclusive optical detection of G4-DNA at lower pH.

| S-EPMC8252107 | biostudies-literature

New fluorescent perylene bisimide indicators--a platform for broadband pH optodes.

Project description:Asymmetric perylene bisimide (PBI) dyes are prepared and are shown to be suitable for the preparation of fluorescence chemosensors for pH. They carry one amino-functional substituent which introduces pH sensitivity via photoinduced electron transfer (PET) while the other one increases solubility. The luminescence quantum yields for the new indicators exceed 75% in the protonated form. The new indicators are non-covalently entrapped in polyurethane hydrogel D4 and poly(hydroxyalkylmethacrylates). Several PET functions including aliphatic and aromatic amino groups were successfully used to tune the dynamic range of the sensor. Because of their virtually identical spectral properties, various PBIs with selected PET functions can easily be integrated into a single sensor with enlarged dynamic range (over 4 pH units). PBIs with two different substitution patterns in the bay position are investigated and possess variable spectral properties. Compared with their tetrachloro analogues, tetra-tert-butyl-substituted PBIs yield more long-wave excitable sensors which feature excellent photostability. Cross-sensitivity to ionic strength was found to be negligible. The practical applicability of the sensors may be compromised by the long response times (especially in case of tetra-tert-butyl-substituted PBIs).

| S-EPMC3100492 | biostudies-literature

A Genetically Encoded Ratiometric pH Probe: Wavelength Regulation-Inspired Design of pH Indicators.

Project description:Mutants of human cellular retinol-binding protein II (hCRBPII) were engineered to bind a julolidine retinal analogue for the purpose of developing a ratiometric pH sensor. The design relied on the electrostatic influence of a titratable amino acid side chain, which affects the absorption and, thus, the emission of the protein/fluorophore complex. The ratio of emissions obtained at two excitation wavelengths that correspond to the absorption of the two forms of the protein/fluorophore complex, leads to a concentration-independent measure of pH.

| S-EPMC6742514 | biostudies-literature

Rational design of a colorimetric pH sensor from a soluble retinoic acid chaperone.

Project description:Reengineering of cellular retinoic acid binding protein II (CRABPII) to be capable of binding retinal as a protonated Schiff base is described. Through rational alterations of the binding pocket, electrostatic perturbations of the embedded retinylidene chromophore that favor delocalization of the iminium charge lead to exquisite control in the regulation of chromophoric absorption properties, spanning the visible spectrum (474-640 nm). The pKa of the retinylidene protonated Schiff base was modulated from 2.4 to 8.1, giving rise to a set of proteins of varying colors and pH sensitivities. These proteins were used to demonstrate a concentration-independent, ratiometric pH sensor.

| S-EPMC4104655 | biostudies-literature

A Convenient Colorimetric Bacteria Detection Method Utilizing Chitosan-Coated Magnetic Nanoparticles.

Project description:An effective novel strategy to detect bacteria is promising because it may improve human health by allowing early diagnosis and timely treatment of bacterial infections. Here, we report a simple, reliable, and economical colorimetric assay using the peroxidase-like activity of chitosan-coated iron oxide magnetic nanoparticles (CS-MNPs). When CS-MNPs are incubated with a sample containing bacterial cells such as the gram-negative Escherichia coli or the gram-positive Staphylococcus aureus, the negatively-charged bacterial membrane interacts with positively-charged chitosan on the surface of CS-MNPs, thus resulting in significant reduction of their peroxidase-like activity presumably by a hindrance in the accessibility of the negatively charged substrate, 2-2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) to the positively-charged CS-MNPs. This simple colorimetric strategy allowed the rapid detection of bacterial cells down to 104 CFU mL-1 by the naked eye and 102 CFU mL-1 by spectrophotometry within 10 min. Based on the results, we anticipate that the CS-MNPs-based assay has great potential for the on-site diagnosis of bacterial infections in facility-limited or point-of-care testing (POCT) environments.

| S-EPMC7023617 | biostudies-literature

Carbonylative cross-coupling of ortho-disubstituted aryl iodides. convenient synthesis of sterically hindered aryl ketones.

Project description:A mild and general protocol for the carbonylative cross-coupling of sterically hindered ortho-disubstituted aryl iodides is reported. Carbonylative Suzuki-Miyaura couplings of a variety of aryl boronic acids provide an array of substituted biaryl ketones in modest to excellent yield. A carbonylative Negishi coupling that utilizes alkynyl nucleophiles is also described.

| S-EPMC2636973 | biostudies-literature

Colorimetric and Fluorimetric DNA Detection with a Hydroxystyryl-Quinolizinium Photoacid and Its Application for Cell Imaging.

Project description:The combination of styryl dye properties with the acidity and strong photoacidity of the 2,2'-[(1''-hydroxy-4''-methyl-(E)-2'',6''-phenylene)]-bisquinolizinium enables the detection of DNA by distinct absorption and emission color changes and the fluorimetric detection of DNA in cells with epifluorescence and confocal fluorescence microscopy.

| S-EPMC6790585 | biostudies-literature

The convenient preparation of stable aryl-coated zerovalent iron nanoparticles.

Project description:A novel approach for the in situ synthesis of zerovalent aryl-coated iron nanoparticles (NPs) based on diazonium salt chemistry is proposed. Surface-modified zerovalent iron NPs (ZVI NPs) were prepared by simple chemical reduction of iron(III) chloride aqueous solution followed by in situ modification using water soluble arenediazonium tosylate. The resulting NPs, with average iron core diameter of 21 nm, were coated with a 10 nm thick organic layer to provide long-term protection in air for the highly reactive zerovalent iron core up to 180 °C. The surface-modified iron NPs possess a high grafting density of the aryl group on the NPs surface of 1.23 mmol/g. FTIR spectroscopy, XRD, HRTEM, TGA/DTA, and elemental analysis were performed in order to characterize the resulting material.

| S-EPMC4464190 | biostudies-literature

Ionic Liquid-Based Fluorescein Colorimetric pH Nanosensors.

Project description:A novel pH sensitive, colorimetric ionic liquid nanosensor based on phosphonium salts of fluorescein is reported. Herein, fluorescein salts of various stoichiometries were synthesized by use of a trihexyltetradecylphosphonium cation [TTP]+ in combination with dianionic [FL]2- and monoanionic [FL]- fluorescein. Nanomaterials derived from these two compounds yielded contrasting colorimetric responses in neutral and acidic environments. Variations in fluorescence spectra as a function of pH were also observed. Examination of TEM and DLS data revealed significant expansion in the diameter of [TTP]2[FL] nanodroplets in acidic environments of variable pHs. A similar trend was also observed for [TTP][FL] nanoparticles. The pH dependent colorimetric and other optical properties of these nanomaterials are attributed to alterations in molecular orientations and stacking as suggested by measuring the absorption, fluorescence, and zeta potential. Since the pH is an important indicator for many diseases, including cancer, these nanosensors are considered to be potential candidates for biomedical applications.

| S-EPMC4174468 | biostudies-literature

A convenient method for synthesis of glyconanoparticles for colorimetric measuring carbohydrate-protein interactions.

Project description:Carbohydrate functionalized nanoparticles, i.e., the glyconanoparticles, have wide application ranging from studies of carbohydrate-protein interactions, in vivo cell imaging, biolabeling, etc. Currently reported methods for preparation of glyconanoparticles require multi-step modifications of carbohydrates moieties to conjugate to nanoparticle surface. However, the required synthetic manipulations are difficult and time consuming. We report herewith a simple and versatile method for preparing glyconanoparticles. This method is based on the utilization of clean and convenient microwave irradiation energy for one-step, site-specific conjugation of unmodified carbohydrates onto hydrazide-functionalized Au nanoparticles. A colorimetric assay that utilizes the ensemble of gold glyconanoparticles and Concanavalin A (ConA) was also presented. This feasible assay system was developed to analyze multivalent interactions and to determine the dissociation constant (K(d)) for five kind of Au glyconanoparticles with lectin. Surface plasmon changes of the Au glyconanoparticles as a function of lectin-carbohydrate interactions were measured and the dissociation constants were determined based on non-linear curve fitting. The strength of the interaction of carbohydrates with ConA was found to be as follows: maltose>mannose>glucose>lactose>MAN5.

| S-EPMC2776624 | 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