Rapid GSH detection and versatile peptide/protein labelling to track cell penetration using coumarin-based probes

Li, Xue; Yu, Dehao; Sun, Jing; Guan, Liangyu; Xie, Cheng‐Zhi; Luo, Wei; Jia, Yuanyuan; Tian, Junyu; Fan, Heli; Sun, Huabing

doi:10.1039/d2an01510b

Cited by 16 publications

(4 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In recent years, remarkable progress has been made in the construction of biothiol fluorescent probes [4,[17][18][19]. Many reported fluorescent probes can be responded to biothiols in cells, tissues, and a variety of amino acids.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

Deng,

Huang,

Feng

et al. 2024

Molecules

View full text Add to dashboard Cite

Monitoring the level of biothiols in organisms would be beneficial for health inspections. Recently, 3-(2′-nitro vinyl)-4-phenylselenyl coumarin as a fluorescent probe for distinguishing the detection of the small-molecule biothiols cysteine/homocysteine (Cys/Hcy) and glutathione (GSH) was developed. By introducing 4-phenyselenium as the active site, the probe CouSeNO2/CouSNO2 was capable of detecting Cys/Hcy and GSH in dual fluorescence channels. Theoretical insights into the fluorescence sensing mechanism of the probe were provided in this work. The details of the electron excitation process in the probe and sensing products under optical excitation and the fluorescent character were analyzed using the quantum mechanical method. All these theoretical results would provide insight and pave the way for the molecular design of fluorescent probes for the detection of biothiols.

show abstract

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

Deng,

Huang,

Feng

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

“…Bioconjugation has been remarkably developed for protein modulation with diverse functionalities, emerging as one of the most powerful tools for biological analysis and clinical diagnosis. − Fluorescent proteins (FPs) such as green fluorescent protein (GFP) have been utilized to fuse with proteins of interest (POIs) for visualizing the localization, trafficking, and interactions of POIs. − However, FPs suffer from the potential perturbation to native protein expression and function . Organic fluorophores, such as coumarins, are well known for bioimaging and biosensing − because of their bright fluorescence and modifiable backbones. − To date, fluorogen-conjugated POIs have gained much attention by covalent or noncovalent incorporation of organic fluorescent dyes onto protein structure, − which renders a POI fluorescent without compromising its function. − Fluorescent versions of POIs provide a spatiotemporal method for the study of protein functions, trapping, and dynamics. ,− Nevertheless, it is still challenging to construct a fluorophore-fused POI with multiple-stimuli-mediated fluorescence responses in vitro and in cells.…”

Section: Introductionmentioning

confidence: 99%

Coumarin-Conjugated Macromolecular Probe for Sequential Stimuli-Mediated Activation

Jiang,

Li,

Ren

et al. 2023

Bioconjugate Chem.

View full text Add to dashboard Cite

Protein bioconjugation has emerged as one of the most valuable tools for the development of protein-based biochemical assays. Here, we report a fluorescent macromolecular material, RF16_Halo, in which the coumarin derivative RF16 is specifically conjugated onto HaloTag protein to achieve a dual-stimuli-mediated fluorescence response. RF16 is first obtained by installing a H 2 O 2 -sensitive boron cage onto the C7 hydroxy moiety of the coumarin fluorophore with a HaloTag ligand attaching to the pH-labile 1,3dioxane moiety. Upon stimulation, RF16_Halo exhibits a sequential fluorescence response to H 2 O 2 /pH at both liquid and solid interfaces. The fluorescence of the RF16_Halo-based protein film increases linearly toward H 2 O 2 with a higher sensitivity when compared with that of RF16. Subsequently, the H 2 O 2 -cleaved RF16_Halo presents a pH-dependent fluorescence decrease under acidic conditions. Such a stimulus-responsive fluorescence "off−on−off" multimode enables RF16_Halo to be applied as a sequential logic circuit. In addition, we evaluate the fluorescence labeling ability of RF16 to intracellular IRE1_Halo protein and demonstrate that RF16 containing the HaloTag ligand could be precisely retained in cells to track IRE1_Halo protein. Hence, we provide a unique structural design strategy to construct a fluorescence dual-responsive macromolecular probe for information encryption and protein tracking in cells.

show abstract

“…The coumarin ring is an important fluorescent skeleton that has been widely employed in dyes and biofluorescent labels. − Discovering novel fluorescent probe is crucial for the development of integrated diagnostic and therapeutic reagents against diseases. − Therefore, we investigated the photophysical properties of compounds 5q and 5s . Initially, the ultraviolet absorption spectra of compounds 5q (40 μM in THF) and 5s (40 μM in THF) were evaluated.…”

mentioning

confidence: 99%

Synthesis of Quinolinoneylnitrones and Coumarinylnitrones via a Cascade Hydroamination and Aza-MBH-Type Reaction

Zhang,

Wang,

Long

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

Nitrones are quite useful intermediates and have been broadly applied in organic synthesis, drug discovery, and photochemistry research. Many functional nitrones have been successfully prepared using various strategies. In this work, an efficient method for synthesizing novel quinolinoneylnitrone and coumarinylnitrone derivatives was developed. Preliminary mechanistic research suggests that this protocol included a cascade hydroamination and aza-MBH-type reaction.

show abstract

Rapid GSH detection and versatile peptide/protein labelling to track cell penetration using coumarin-based probes

Abstract: Biothiols play essential roles in balancing redox state and modulating cellular functions. Fluorescent probes for monitoring/labelling biothiols often suffer from slow reaction rates, strong background fluorescence and cytotoxic byproducts release....

Cited by 16 publications

References 47 publications

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

Theoretical Investigation of a Coumarin Fluorescent Probe for Distinguishing the Detection of Small-Molecule Biothiols

Coumarin-Conjugated Macromolecular Probe for Sequential Stimuli-Mediated Activation

Synthesis of Quinolinoneylnitrones and Coumarinylnitrones via a Cascade Hydroamination and Aza-MBH-Type Reaction

Contact Info

Product

Resources

About