Many studies have shown that glutathione (GSH) and cysteine (Cys) / homocysteine (Hcy) levels are interrelated in biological systems. To unravel the complicated biomedical mechanisms by which GSH and Cys/Hcy are involved in various disease states, probes that display distinct signals in response to GSH and Cys/Hcy are highly desirable. In this work, we report a rhodol thioester () that responds to GSH and Cys/Hcy with distinct fluorescence emissions in neutral media. Probe reacts with Cys/Hcy to form the corresponding deconjugated spirolactam via a tandem native chemical ligation (NCL) reaction. This intramolecular spirocyclization leads to the "quinone - phenol" transduction of rhodol dyes, and an excited-state intramolecular proton transfer (ESIPT) process between the phenolic hydroxyl proton and the aromatic nitrogen in the benzothiazole unit occurs upon photoexcitation, thus affording 2-(2'-hydroxyphenyl) benzothiazole (HBT) emission (454 nm). In the case of the tripeptide GSH, only transthioesterification takes place removing the intramolecular photo-induced electron transfer (PET) process caused by the electron deficient 4-nitrobenzene moiety giving rise to a large fluorescence enhancement at the rhodol emission band (587 nm). The simultaneous detection of GSH and Cys/Hcy is attributed to the significantly different rates of intramolecular S,N-acyl shift of their corresponding thioester adducts derived from . The utility of probe has been demonstrated in various biological systems including serum and cells.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4074921 | PMC |
| http://dx.doi.org/10.1039/C4SC00308J | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A new pyranopyrazole based colorimetric chemosensor for the selective recognition of biothiols: applications in real samples.
Anal Methods
December 2024
Bio-organic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India.
Here, we present the development of a pyranopyrazole-based chemosensor (P1) that serves as a reliable colorimetric chemosensor for the identification of biothiols, namely glutathione (GSH), homocysteine (Hcy), and cysteine (Cys). We extensively studied the interaction of P1 with several amino acids (Cys, Ala, His, Ile, Leu, Lys, Ser, Trp, Val, Pro, Phe, Arg) and other biothiols (Hcy and GSH) using colorimetric methods and UV-visible spectroscopy. The results indicated that P1 endures a visible color change in the presence of biothiols, rendering it a practical tool for detection.
View Article and Find Full Text PDFUnravelling the recent advancement in fluorescent probes for detection against reactive sulfur species (RSS) in foodstuffs and cell imaging.
Food Chem
February 2025
Institute for Advanced Study, Shenzhen University, Shenzhen 518060, PR China. Electronic address:
Sulfur-containing representative HSO/SO, HS, and biothiols (Cys, Hcy, and GSH) present in food items and biological organisms have raised substantial global concerns about food safety due to their reactivity and potential health implications. Adhering to international health standards is essential for these compounds; in particular, plenty of challenges exist in ensuring product quality in the beverage industry. Many fluorescent probes are being employed in various spectroscopic techniques and have developed rapidly to selectively detect sulfur-related species in food products and bio-sensing for cell imaging.
View Article and Find Full Text PDFA mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe for biothiols with large Stokes shift based on thiol-chromene click reaction.
Org Biomol Chem
November 2024
MOE Key Laboratory for Cellular Dynamics, Hefei National Center for Physical Sciences at Microscale, University of Science and Technology of China, Hefei 230026, PR China.
In this study, a carbazole-based mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe 1 for biothiols based on the thiol-chromene click reaction was subtly designed and synthesized. Upon interaction with biothiols (Cys, Hcy and GSH), the absorption of 1 shifted from 496 nm to 388 nm, while its fluorescence spectrum shifted from 650 nm to 530 nm. These transformations were accompanied by a visible color change from pink to colorless under visible light and from red to green when observed under a 365 nm UV lamp, which can be attributed to the click reaction of biothiols with the α,β-unsaturated ketone of the chromene moiety, subsequent pyran ring-opening and phenol formation as well as 1,6-elimination of a -hydroxybenzyl moiety yielding 2.
View Article and Find Full Text PDFFluorescent discrimination of cysteine, homocysteine, and glutathione in urine samples using a novel seleno-BODIPY probe.
J Mater Chem B
November 2024
BIOSCOPE Research Group, LAQV-REQUIMTE, Department of Chemistry, NOVA-FCT, NOVA University Lisbon, 2829-516 Caparica, Portugal.
Biothiols, such as cysteine (Cys), glutathione (GSH), and homocysteine (Hcy), play crucial roles in various physiological processes and serve as biomarkers for oxidative stress and redox homeostasis. Their structural similarities, however, pose significant challenges in selective detection and quantification, limiting the availability of suitable probes. Here, we report the design and synthesis of a novel ratiometric fluorescent sensor based on a seleno-BODIPY (Se-BODIPY) derivative, enabling rapid discrimination and quantification of Cys, Hcy, and GSH with low detection limits (Cys = 0.
View Article and Find Full Text PDFDual-Channel fluorescent detection of Biothiols: A novel probe for Distinguishing Cysteine, Homocysteine, Glutathione, and N-Acetylcysteine in cellular environments.
Spectrochim Acta A Mol Biomol Spectrosc
February 2025
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China. Electronic address:
Article Synopsis
- Biothiols like cysteine (Cys), homocysteine (Hcy), glutathione (GSH), and N-acetylcysteine (NAC) are similar in structure but serve different biological functions, and their imbalance is linked to various diseases.
- The study developed a novel dual-channel fluorescent probe, CNTC, that can effectively differentiate Cys from Hcy, GSH, and NAC using distinct fluorescent signals (blue for Cys, green for others).
- CNTC demonstrated quick reaction times and sensitive detection limits for each biothiol, and was successfully used for imaging these compounds in live cells, making it a valuable tool for studying their biological significance.
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!