Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Flavone-based ESIPT ratiometric chemodosimeter for detection of cysteine in living cells.

ABSTRACT: We have designed and synthesized a novel ratiometric fluorescent chemodosimeter MHF-based ESIPT process for specific detection of cysteine among the biological thiols. The probe MHF shows very weak blue fluorescence under UV excitation. Upon addition of cysteine (Cys), the reaction of Cys with MHF induces acrylate hydrolysis, thereby enabling the ESIPT process to shift the weak blue emission to a strong green emission with about 20-fold enhancement. We utilized (1)H NMR spectra to elucidate the fluorescence sensing mechanism. Moreover, the cellular imaging experiment indicated the MHF possessed excellent selectivity, low cytotoxicity, and desirable cell permeability for biological applications.

SUBMITTER: Liu B

PROVIDER: S-EPMC3985879 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Flavone-based ESIPT ratiometric chemodosimeter for detection of cysteine in living cells.

Liu Bin B Wang Junfeng J Zhang Ge G Bai Ruke R Pang Yi Y

ACS applied materials & interfaces 20140306 6

We have designed and synthesized a novel ratiometric fluorescent chemodosimeter MHF-based ESIPT process for specific detection of cysteine among the biological thiols. The probe MHF shows very weak blue fluorescence under UV excitation. Upon addition of cysteine (Cys), the reaction of Cys with MHF induces acrylate hydrolysis, thereby enabling the ESIPT process to shift the weak blue emission to a strong green emission with about 20-fold enhancement. We utilized (1)H NMR spectra to elucidate the ...[more]

PMID: 24571859

Similar Datasets

The sensing mechanism of a flavone-based ESIPT fluorescent chemodosimeter for selective recognition towards fluoride: a theoretical.

Project description:The sensing mechanism of 3-hydroxyflavone-based (3-HF) fluorescent chemodosimeter 3-triisopropylsilylflavone (3-TPSF) for detecting fluoride (F-) has been theoretically investigated. The calculated Laplacian bond order confirms that the Si-O bond of 3-TPSF is the reaction site of F-. The free energy barrier of 18.33 kcal mol-1 indicates that F-triggered desilylation reaction can occur and then form the anionic state of 3-HF (3-HF-) with a fluorescence peak at 545 nm. 3-HF- captures H+ of the mixed aqueous medium to be transformed into 3-HF with an intramolecular hydrogen bond (O1-H⋯O2). The energy barrier of 1.86 kcal mol-1 in the S1 state obtained from the constructed potential energy curves confirms that the excited state intramolecular proton transfer (ESIPT) in 3-HF occurs to form a tautomer structure, which produces a long-wavelength emission of 549 nm. The fluorescence emitted from both 3-HF- and 3-HF agrees with the experimental value of 530 nm appearing after adding F-. Charge transfer analyses indicate that the extent of intramolecular charge transfer in 3-HF- is more intense than that of 3-TPSF, which induces a large Stokes shift of 180 nm. Therefore, the sensing mechanism is attributed to the combination of a large charge transfer feature and ESIPT that are caused by desilylation reaction. The significant fluorescence change makes 3-TPSF a chemodosimeter for detecting F-.

| S-EPMC8979047 | biostudies-literature

An ESIPT-Based Ratiometric Fluorescent Probe for Highly Sensitive and Rapid Detection of Sulfite in Living Cells.

Project description:The novel ratiometric fluorescent probe HPQRB with an ESIPT effect based on Michael addition for highly sensitive and fast detection of sulfite in living HepG2 cells is reported. HPQRB can be easily synthesized by a two-step condensation reaction. HPQRB has a large emission shift (Δλ=116 nm), which is beneficial for fluorescence imaging research, and its sulfite-responsive site is based on a rhodamine-like structure with the emission peak at 566 nm, which decreases with increasing sulfite concentration. and its HPQ structure always has an ESIPT effect throughout the reaction process, keeping the emission peak at 450 nm as a self-reference. In particular, HPQRB has high selectivity for sulfite and responds quickly (within 30 s) with a low detection limit (44 nM). Furthermore, HPQRB has been successfully used for fluorescence imaging of sulfite in HepG2 cells, demonstrating the superior ability to detect sulfite under physiological conditions.

| S-EPMC6779067 | biostudies-literature

A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells.

Project description:Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play a key role in an extensive range of physiological processes and biological functions. Therefore, the selective and sensitive detection of intracellular thiols is important for revealing cellular function. In this study, ethyl 2-(4-(acryloyloxy)-3-formylphenyl)-4-methylthiazole-5-carboxylate (NL-AC) was designed and synthesized as a colorimetric and ratiometric fluorescent probe that can be utilized to rapidly, sensitively and selectively detect biothiols in physiological media. The fluorescence intensity of this probe using the three target biothiols at a concentration of 20 equiv. of the probe increased by approximately 6~10-fold in comparison to that without the biothiols in aqueous solution. The limits of detection (LOD) for Cys, Hcy and GSH were 0.156, 0.185, and 1.838 μM, respectively. In addition, both 1H-NMR and MS analyses suggested the mechanism of fluorescence sensing to be excited-state intramolecular proton transfer (ESIPT). The novel colorimetric and ratiometric probe is structurally simple and offers detection within 20 min. Furthermore, this probe can be successfully applied in bioimaging. The results indicate high application potential in analytical chemistry and diagnostics.

| S-EPMC5491497 | biostudies-literature

A seminaphthofluorescein-based fluorescent chemodosimeter for the highly selective detection of cysteine.

Project description:A fluorescent chemodosimeter for cysteine detection was developed based on a tandem conjugate addition and intramolecular cyclization reaction. The method exhibited an excellent selectivity for cysteine over other biothiols such as homocysteine and glutathione.

| S-EPMC3386612 | biostudies-literature

A Novel Dicyanoisophorone-Based Ratiometric Fluorescent Probe for Selective Detection of Cysteine and Its Bioimaging Application in Living Cells.

Project description:A selective and ratiometric turn-on fluorescent probe was designed and synthesized by using a novel dicyanoisophorone-based derivative and acrylate moiety. The probe displayed high stability and good selectivity to cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). It also exhibited rapid response to Cys within 180 s. Most importantly, the fluorescence intensity ratio at 590 and 525 nm (I590/I525) was linearly dependent on the Cys concentration in the range from 0 to 40 μM and the detection limit calculated to be 0.48 μM. This probe was also applied for bioimaging of intracellular Cys in living HeLa cells with low cytotoxicity.

| S-EPMC6017397 | biostudies-literature

ESIPT-Based Photoactivatable Fluorescent Probe for Ratiometric Spatiotemporal Bioimaging.

Project description:Photoactivatable fluorophores have become an important technique for the high spatiotemporal resolution of biological imaging. Here, we developed a novel photoactivatable probe (PHBT), which is based on 2-(2-hydroxyphenyl)benzothiazole (HBT), a small organic fluorophore known for its classic luminescence mechanism through excited-state intramolecular proton transfer (ESIPT) with the keto form and the enol form. After photocleavage, PHBT released a ratiometric fluorophore HBT, which showed dual emission bands with more than 73-fold fluorescence enhancement at 512 nm in buffer and more than 69-fold enhancement at 452 nm in bovine serum. The probe displayed a high ratiometric imaging resolution and is believed to have a wide application in biological imaging.

| S-EPMC5087472 | biostudies-literature

A novel ratiometric AIEE/ESIPT probe for palladium species detection with ultra-sensitivity.

Project description:Existing fluorescent probes for palladium (Pd) species detection have revealed their vulnerabilities, such as low sensitivity, poor anti-interference ability and long reaction time. In order to develop a faster and more accurate detection method for palladium species at extremely low concentrations, in this study, we designed a novel ratiometric AIEE/ESIPT probe (HPNI-1) based on the Tsuji-Trost reaction for Pd. According to the data obtained, the probe was able to detect Pd species with an ultra-high anti-interference ability (Pd : other metals = 1 : 1000), rapid detection time (within 2 minute) and ratiometric fluorescent signal changes with a 1.34 nM detection limit. This study not only proves that existing methods can be improved but also provides future prospects for HPNI-1 as one of the greatest probes for Pd species detection.

| S-EPMC9070796 | biostudies-literature

ESIPT Fluorescence Probe Based on Double-Switch Recognition Mechanism for Selective and Rapid Detection of Hydrogen Sulfide in Living Cells.

Project description:A novel fluorescence probe, HBTSeSe, was designed and synthesized for the detection of H2S with a double-switch mechanism of a broken diselenide bond followed by thiolysis of ether. Then, 2-(2'-hydroxyphenyl)benzothiazole (HBT) was released as fluorophore, which has large Stokes shift based on the excited state intramolecular proton transfer process. The probe responded selectively and rapidly to H2S, with the fluorescence increased by 47-fold immediately after the addition of H2S. HBTSeSe was able to detect H2S in the cytoplasm, specifically in cell imaging experiments. The results also showed that H2S was produced in the immune response of RAW264.7 cells activated by phorbol-12-myristate-13-acetate.

| S-EPMC6648457 | biostudies-literature

A FRET-Based Near-Infrared Fluorescent Probe for Ratiometric Detection of Cysteine in Mitochondria.

Project description:We report a near-infrared fluorescent probe A for the ratiometric detection of cysteine based on FRET from a coumarin donor to a near-infrared rhodamine acceptor. Upon addition of cysteine, the coumarin fluorescence increased dramatically up to 18-fold and the fluorescence of the rhodamine acceptor decreased moderately by 45 % under excitation of the coumarin unit. Probe A has been used to detect cysteine concentration changes in live cells ratiometrically and to visualize fluctuations in cysteine concentrations induced by oxidation stress through treatment with hydrogen peroxide or lipopolysaccharide (LPS). Finally, probe A was successfully applied for the in vivo imaging of Drosophila melanogaster larvae to measure cysteine concentration changes.

| S-EPMC6676905 | biostudies-literature

An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO<sup>-</sup> in living cells.

Project description:Based on ESIPT, we designed and synthesized a naphthalimide chemosensor N-CBT for selectively visualizing endo/exogenous peroxynitrite (ONOO-) in living cells. The incorporation of 2-benzothiazoleacetonitrile offers N-CBT a rare pre-existing eight-membered ring hydrogen bonding configuration, which is able to generate two types of emission of naphthalimide. Confirmed by calculation results, fast proton transfer from the hydroxyl group to the carbonyl group occurs along with excited-state energy transfer via the intramolecular H-bond, leading to a tautomeric transformation from the excited enol form to the excited keto form. In aqueous solution, the formation of intermolecular hydrogen bonding with water perturbs ESIPT and destroys the stable planar construction. By breaking the cyano carbon-carbon double bond in the presence of ONOO-, green fluorescence can be regenerated efficiently. As a result, 34-fold fluorescence enhancement at 518 nm was observed in response, and it showed a good linear relationship in the range of 1 to 14 μM with a detection limit of 37 nM. Subsequently, N-CBT was applied in visualizing cellular ONOO-, and it demonstrated great potential in selectively visualizing endo/exogenous peroxynitrite (ONOO-) in living cells.

| S-EPMC9077266 | 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