Browse
Submit Data
Databases
API
Help

Dataset Information

41 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Barbituric Acid Based Fluorogens: Synthesis, Aggregation-Induced Emission, and Protein Fibril Detection.

ABSTRACT: Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure-property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.

SUBMITTER: Ding S

PROVIDER: S-EPMC6982923 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Barbituric Acid Based Fluorogens: Synthesis, Aggregation-Induced Emission, and Protein Fibril Detection.

Ding Siyang S Yao Bicheng B Schobben Louis L Hong Yuning Y

Molecules (Basel, Switzerland) 20191220 1

Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced em ...[more]

PMID: 31861868

Similar Datasets

Gelation process visualized by aggregation-induced emission fluorogens.

Project description:Alkaline-urea aqueous solvent system provides a novel and important approach for the utilization of polysaccharide. As one of the most important polysaccharide, chitosan can be well dissolved in this solvent system, and the resultant hydrogel material possesses unique and excellent properties. Thus the sound understanding of the gelation process is fundamentally important. However, current study of the gelation process is still limited due to the absence of direct observation and the lack of attention on the entire process. Here we show the entire gelation process of chitosan LiOH-urea aqueous system by aggregation-induced emission fluorescent imaging. Accompanied by other pseudo in situ investigations, we propose the mechanism of gelation process, focusing on the formation of junction points including hydrogen bonds and crystalline.

| S-EPMC4931011 | biostudies-literature

Hyaluronan-based graft copolymers bearing aggregation-induced emission fluorogens.

Project description:In order to develop a technology platform based on two natural compounds from biorenewable resources, a short series of hyaluronan (HA) copolymers grafted with propargylated ferulic acid (HA-FA-Pg) were designed and synthesized to show different grafting degree values and their optical properties were characterized in comparison with reference compounds containing the same ferulate fluorophore. Interestingly, these studies revealed that the ferulate fluorophore was quite sensitive to the restriction of intramolecular motion and its introduction into the rigid HA backbone, as in HA-FA-Pg graft copolymers, led to higher photoluminescence quantum yield values than those obtained with the isolated fluorophore. Thus, the propargyl groups of HA-FA-Pg derivatives were exploited in the coupling with oleic acid through a biocompatible nona(ethylene glycol) spacer as an example of the possible applications of this technology platform. The resulting HA-FA-NEG-OA materials showed self-assembling capabilities in aqueous environment. Furthermore, HA-FA-NEG-OA derivatives have been shown to interact with phospholipid bilayers both in liposomes and living cells, retaining their fluorogenic properties and showing a high degree of cytocompatibility and for this reason they were proposed as potential biocompatible self-assembled aggregates forming new materials for biomedical applications.

| S-EPMC9078255 | biostudies-literature

DNA quadruplexes as molecular scaffolds for controlled assembly of fluorogens with aggregation-induced emission.

Project description:Aggregation-induced emission (AIE) can be generated due to the restriction of intramolecular motions. The controllable assembly of fluorogens with AIE properties (AIEgens) is able to provide a new opportunity for precise manipulation of fluorescent signal transduction. Here, a tetrapod DNA quadruplex (TP-G4) was designed as a molecular scaffold for assembly and precise modulation of light emission of an oligonucleotide-grafted fluorogen with aggregation-induced emission (Oligo-AIEgen). The Oligo-AIEgen was synthesized by attaching the AIEgen to the 3'-terminus of the oligonucleotide through a dibenzylcyclooctyne mediated coupling reaction. The AIEgen emitted no detectable fluorescence in the context of a double-stranded structure. When hybridized to the parallel-stranded TP-G4, several AIEgens were located in close proximity to generate fluorescence. The fluorescence intensity has been precisely regulated by manipulation of the spacer length between the core structure of the scaffold and AIEgen, as well as by altering the quartet number of the G-quadruplex. Similar control of fluorescence was also demonstrated using tetramolecular and bimolecular i-motif quadruplex structures as the scaffolds. These scaffolds provide a proof of concept on the manipulation of molecular interactions, which forms a universal molecular tool for the design of new biosensing strategies.

| S-EPMC5911820 | biostudies-literature

Synthesis and structure of push-pull merocyanines based on barbituric and thio-barbituric acid.

Project description:Two compounds, 1,3-diethyl-5-{(2E,4E)-6-[(E)-1,3,3-tri-methyl-indolin-2-yl-idene]hexa-2,4-dien-1-yl-idene}pyrimidine-2,4,6(1H,3H,5H)-trione or TMI, C25H29N3O3, and 1,3-diethyl-2-sulfanyl-idene-5-[2-(1,3,3-tri-methyl-indolin-2-yl-idene)ethyl-idene]di-hydro-pyrimidine-4,6(1H,5H)-dione or DTB, C21H25N3O2S, have been crystallized and studied. These compounds contain the same indole derivative donor group and differ in their acceptor groups (in TMI it contains oxygen in the para position, and in DTB sulfur) and the length of the π-bridge. In both materials, mol-ecules are packed in a herringbone manner with differences in the twist and fold angles. In both structures, the mol-ecules are connected by weak C-H⋯O and/or C-H⋯S bonds.

| S-EPMC6727061 | biostudies-literature

CRISPR/Cas-mediated "one to more" lighting-up nucleic acid detection using aggregation-induced emission luminogens.

Project description:CRISPR diagnostics are effective but suffer from low signal transduction efficiency, limited sensitivity, and poor stability due to their reliance on the trans-cleavage of single-stranded nucleic acid fluorescent reporters. Here, we present CrisprAIE, which integrates CRISPR/Cas reactions with "one to more" aggregation-induced emission luminogen (AIEgen) lighting-up fluorescence generated by the trans-cleavage of Cas proteins to AIEgen-incorporated double-stranded DNA labeled with single-stranded nucleic acid linkers and Black Hole Quencher groups at both ends (Q-dsDNA/AIEgens-Q). CrisprAIE demonstrates superior performance in the clinical nucleic acid detection of norovirus and SARS-CoV-2 regardless of amplification. Moreover, the diagnostic potential of CrisprAIE is further enhanced by integrating it with spherical nucleic acid-modified AIEgens (SNA/AIEgens) and a portable cellphone-based readout device. The improved CrisprAIE system, utilizing Q-dsDNA/AIEgen-Q and SNA/AIEgen reporters, exhibits approximately 80- and 270-fold improvements in sensitivity, respectively, compared to conventional CRISPR-based diagnostics. We believe CrisprAIE can be readily extended as a universal signal generation strategy to significantly enhance the detection efficiency of almost all existing CRISPR-based diagnostics.

| S-EPMC11450156 | biostudies-literature

Synthesis and Tetraphenylethylene-Based Aggregation-Induced Emission Probe for Rapid Detection of Nitroaromatic Compounds in Aqueous Media.

Project description:Tetraphenylethylene (TPE) can be used to construct fluorescent probes with typical aggregation-induced emission (AIE) behavior for next-generation sensing applications. McMurry coupling and Suzuki cross coupling strategies provided the desired sensor thiophene-substituted tetraphenylethylene (THTPE). The synthesized TPE analogues were characterized by NMR spectroscopy and mass spectrometry. Maximum AIE of THTPE was observed in 90% water (H2O/THF) content due to extensive formation of aggregates. The AIE properties of THTPE have been utilized for facile detection of nitroaromatic compounds (NACs) (1.0 nM) through a fluorescence quenching mechanism. A paper strip adsorbed with the AIE-based THTPE fluorophore is developed for rapid and convenient detection of NAC-based analytes. Further, interaction of THTPE with analytes is also studied via Gaussian software at the DFT/B3LYP/6-31G(d) level of theory. Interaction energy, frontier molecular orbitals (FMOs), and non-covalent interaction (NCI) analyses are studied by using the same method. Computational results revealed that nitrobenzene (NB) has the strongest interaction while 1,3-dinitrobenzene (DNB) exhibits the least interaction with the sensor molecule. These computational results clearly demonstrate good agreement with experimental data.

| S-EPMC8495881 | biostudies-literature

Synthesis of Novel Biocompatible Thienopyrimidine Chromophores with Aggregation-Induced Emission Sensitive to Molecular Aggregation.

Project description:Biocompatible luminogens with aggregation-induced emission (AIE) have several applications in the biology field, such as in detecting biomacromolecules bioprobes and in bio-imaging. Due to their bioactivities and light-emitting properties, many heterocyclic compounds are good candidates for such applications. However, heterocyclic π-conjugated systems with AIE behavior remain rare as strong intermolecular π-π interactions usually quench their emission. In this work, new thienopyrimidine heterocyclic compounds were synthesized and their structures were verified by elemental analysis and Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. The photophysical properties of some compounds were investigated in the solution and solid states. Density functional theory calculations were also performed to confirm the observed photophysical properties of the compounds. The studied dyes displayed AIE properties with spectral shapes related to the aggregate structure and a quantum yield up to 10.8%. The emission efficiency of the powder is attributed to the incorporation of multiply rotatable and twisted aryl groups to the fused heterocyclic moieties. The dyes also showed high thermal stability and potent antimicrobial activities against numerous bacterial and fungal strains. Additionally, the cytotoxicity of the new compounds was evaluated against the Caco-2 cell line, and molecular docking was used to investigate the binding conformation of the most effective compound with the MNK2 enzyme. Therefore, the presented structures may potentially be used for bioapplications.

| S-EPMC7689934 | biostudies-literature

Four-layer folding framework: design, GAP synthesis, and aggregation-induced emission.

Project description:The design and synthesis of a type of [1 + 4 + 2] four-layer framework have been conducted by taking advantage of Suzuki-Miyaura cross-coupling and group-assisted purification (GAP) chemistry. The optimized coupling of double-layer diboronic esters with 1-bromo-naphth-2-yl phosphine oxides resulted in a series of multilayer folding targets, showing a broad scope of substrates and moderate to excellent yields. The final products were purified using group-assisted purification chemistry/technology, achieved simply by washing crude products with 95% EtOH without the use of chromatography and recrystallization. The structures were fully characterized and assigned by performing X-ray crystallographic analysis. UV-vis absorption, photoluminescence (PL), and aggregation-induced emission (AIE) were studied for the resulting multilayer folding products.

| S-EPMC10450629 | biostudies-literature

Multiplex detection of miRNAs based on aggregation-induced emission luminogen encoded microspheres.

Project description:Herein, we report a multiplex detection platform based on a suspension array with aggregation-induced emission luminogen (AIEgen) barcodes for simultaneous quantitative measurement of let-7b-5p, miR-16-5p and miR-19b-3p, which are associated with gastric cancer. A detection strategy by using a flow cytometer is proposed, which utilizes AIEgen-encoded microspheres to quantify the target miRNAs, and phycoerythrin as a fluorescence reporter on the detection probes to provide quantitative signals. This multiplex assay shows good specificity for recognizing single base mismatch, and possesses excellent sensitivity with limits of detection (LODs) ranging from 0.43 to 0.76 nM for the three miRNAs. The approach could be extended to the simultaneous detection of more target miRNAs by designing specific detection probes and increasing the number of fluorescence barcodes. We could foresee it holding great potential in future laboratory research and clinical applications due to its flexibility, strong multiplexed ability and good detection performance.

| S-EPMC9076168 | biostudies-literature

A novel aggregation-induced enhanced emission aromatic molecule: 2-aminophenylboronic acid dimer.

Project description:Aggregation-induced enhanced emission (AIEE) molecules have significant applications in optoelectronics, biomedical probes and chemical sensors, and large amounts of AIEE molecules have been reported since the concept of AIEE was proposed. Most aromatic AIEE molecules have complex structures consisting of multiple aromatic rings and/or polycyclic skeletons. In this study, we find that 2-aminophenylboronic acid (2-APBA) with a simple structure is highly emissive in the solid state. Further studies reveal that 2-APBA exists in a dimeric form, and the 2-APBA dimer is a novel AIEE molecule. The underlying AIEE mechanism is that the 2-APBA dimeric units aggregate through intermolecular interactions to produce highly ordered molecular packing without the presence of π-π stacking interactions that would lead to aggregation-caused quenching. Furthermore, the 2-APBA dimer aggregates could reversibly transform into its non-fluorescent monomer form driven by new kinds of dynamic covalent B-N and B-O bonds, illustrating its good potential in molecular recognition, nanogating, chemo/bio-sensing and controlled drug release.

| S-EPMC8480421 | 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