Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

Wu, Xiaolei; Shu, Hai; Zhou, Baojing; Geng, Yougliang; Bao, Xiaofeng; Zhu, Jing

doi:10.1016/j.snb.2016.06.161

Cited by 22 publications

(4 citation statements)

References 51 publications

(50 reference statements)

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“…In both cases this may reflect reduced nucleophilicity [ 41 , 42 ]. To our delight, the sensor showed no affinity toward cysteine, an observation consistent with other reported GSH mechanistic sensors [ 11 , 13 , 37 ]. Competition assays were also carried out to determine the selectivity of sensor 1 for GSH in the presence of a competing analyte.…”

Section: Resultssupporting

confidence: 89%

“…This is consistent with the formation of the SP isomer, possibly by a conjugate addition of GSH to 1-MC followed by cyclisation, as outlined in Figure 4 . GSH is known to undergo conjugate addition, and this has been used as the basis of a number of sensors [ 11 , 13 , 37 ]. The solution was irradiated with UV light (λ = 365 nm) to switch the sensor back to the more colored MC isomer, with a re-appearance of the absorption in the region of 512–522 nm.…”

Section: Resultsmentioning

confidence: 99%

“…γ-Glutamyl-cysteinyl-glycine (GSH) is the most abundant thiol in biological systems [ 1 , 2 ], with a central role in critical cellular functions including redox regulation and cellular signalling [ 3 , 4 , 5 , 6 , 7 ]. Current strategies for its sensing include high performance liquid chromatography [ 8 ], gas chromatography-mass spectrometry [ 9 ], electro-chemical assays [ 10 ] , and spectroscopic detection using fluorescent chemosensors [ 11 , 12 , 13 ]. Typical fluorescent ‘turn on’ chemosensors function as reaction-based probes, binding to GSH irreversibly with a high sensitivity and selectivity [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

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A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione

et al. 2017

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γ-Glutamyl-cysteinyl-glycine (GSH) plays a critical role in maintaining redox homeostasis in biological systems and a decrease in its cellular levels is associated with diseases. Existing fluorescence-based chemosensors for GSH acts as irreversible reaction-based probes that exhibit a maximum fluorescence (‘turn-on’) once the reaction is complete, regardless of the actual concentration of GSH. A reversible, reaction-based ‘turn-off’ probe (1) is reported here to sense the decreasing levels of GSH, a situation known to occur at the onset of various diseases. The more fluorescent merocyanine (MC) isomer of 1 exists in aqueous solution and this reacts with GSH to induce formation of the ring-closed spiropyran (SP) isomer, with a measurable decrease in absorbance and fluorescence (‘turn-off’). Sensor 1 has good aqueous solubility and shows an excellent selectivity for GSH over other biologically relevant metal ions and aminothiol analytes. The sensor permeates HEK 293 cells and an increase in fluorescence is observed on adding buthionine sulfoximine, an inhibitor of GSH synthesis.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione

et al. 2017

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“…Derivatives of maleic anhydride inhibit cell viability and induce apoptosis, probably through decreasing mitochondrial GSH levels [8,9]. Through in silico studies, it has been proposed that 3,5dimaleamylbenzoic acid (C1) and 3,5-dimaleimylbenzoic acid (C2), both derivatives of maleic anhydride, are highly selective for the SH group of GSH through conjugation reactions towards the 1,2-addition carbonyl group and have relatively high selectivity towards the ole nic carbons by 1,4-Michael-type addition [10,11]. In the search for new alternative treatments, it is proposed that for cancer cell-targeted treatment, pharmacological agents that have pro-oxidant effects mediated by increasing the generation of ROS at the cytosolic level or by abrogating the antioxidant defense system in tumor cells should be considered.…”

Section: Introductionmentioning

confidence: 99%

Synergistic Inhibitory Effect of Maleic Anhydride Derivatives and Quercetin on Cervical Cancer Cells Mediated by Attenuating Cell Survival through Modification of the GSH System

Torres

Millán-Casarrubias

Monroy-Ramírez

et al. 2021

Preprint

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Oxidative stress is considered apromotive factor in cervical cancer progression. Agents that decrease cellular GSH levels have been reported to modulate the proliferation rate of cancer cells. To explore a new therapeutic candidate for cervical cancer, we evaluated the effects of combined administration of a maleic anhydride derivative and quercetin on a human cervical cancer-derived (HeLa) cell line and human epithelial cell lines (HaCaT, THLE-3 and cultured primary cells). The combinatorial treatment sensitizes tumor cells through significant decreases in ROS and GSH levels, inducing apoptotic cell death, which was probably induced by disruption of cellular redox homeostasis. In addition, S-phase cell cycle arrest, decreased cell migration and clear evidence of changes in cytoskeletal actin and core morphology were observed in HeLa cells at 24 and 48 h after treatment. In an in vivo model, we observed an increase in the survival time of animals given the combination treatment, as well as tumor inhibition. Therefore, current data suggest that this alteration in the cellular redox state mediated through coadministration of established agentsmay be a promising chemotherapeutic approach.

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Two‐photon Dye‐Based Fluorogenic Organic Nanoparticles as Intracellular Thiols Sensors

Dal Pra,

Daniel,

Recher

et al. 2024

Small Methods

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Optical bioimaging is an ever‐growing field that benefits both from the fast progress of optical instrumentation and modalities, and from the development of light‐emitting probes. The efficacy of molecular fluorescent dyes is crucial, yet hindered by limited brightness and hydrophilicity. Addressing these challenges, self‐stabilized fluorogenic organic nanoparticles only made of pure dyes (dFONs) are introduced in this work. Comprising thiol‐sensitive fluorogenic chromophores, these dFONs exhibit enhanced brightness exclusively in the presence of biological thiols, notably glutathione, overcoming the need for water‐solubilizing moieties. Importantly, these nanoparticles demonstrate large fluorescence and one‐ and two‐photon brightness, enabling sensitive bioimaging of intracellular thiols at micromolar concentrations. Notably, only the pristine fluorogenic nanoparticles can penetrate the cells and does not require to wash the cells before imaging, emphasizing their unique role as dye carriers, fluorogenic probes and ease of use. This work highlights the transformative potential of dFONs in advancing optical bioimaging, paving the way for the use of dFONs not just as tracers, but also now as biosensors and ultimately in the future as biomarkers.

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Design and synthesis of a new rhodamine B-based fluorescent probe for selective detection of glutathione and its application for live cell imaging

Cited by 22 publications

References 51 publications

A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione

A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione

Synergistic Inhibitory Effect of Maleic Anhydride Derivatives and Quercetin on Cervical Cancer Cells Mediated by Attenuating Cell Survival through Modification of the GSH System

Two‐photon Dye‐Based Fluorogenic Organic Nanoparticles as Intracellular Thiols Sensors

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