Cationic red-emitting probes for the rapid and selective detection of SO<sub>2</sub> derivatives in aqueous and cellular environments

Jana, Palash; Patel, Nishaben; Soppina, Virupakshi; Kanvah, Sriram

doi:10.1039/c8nj04669g

Cited by 30 publications

(9 citation statements)

References 39 publications

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“…Upon treating the dye-incubated cells with two different concentrations of sulfite SO3 2− (0.3 mM and 30 mM), a decrease in emission in the 630-720 nm range followed by an increase of emission in the 430-510 nm range is observed, indicating the exogenous detection of sulfite. The sulfite was also generated endogenously, and similar observations were noted with the decrease in emission intensity 49 .…”

Section: Sensing Of Sulfitesupporting

confidence: 68%

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Functional α-Cyanostilbenes: Sensing to Imaging

Dahiwadkar

Kaloo

Kanvah³

2023

Synlett

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In recent years, there has been considerable interest in cyanostilbenes due to their unique photophysical properties. The compounds emit light when aggregating, commonly called aggregation-induced emission (AIE). This remarkable feature makes cyanostilbenes ideal for various sensing applications, especially in aqueous environments. The detection of various analytes, such as metal ions and nitroaromatic compounds, has been accomplished using these compounds through various sensing mechanisms from chelation-enhanced fluorescence to fluorescence quenching. Furthermore, cyanostilbenes have shown great promise in biological imaging applications and have been employed for intracellular imaging, tracking, and targeting of sub-cellular organelles. The development and utilization of cyanostilbenes can significantly impact advancing sensing and imaging technologies in both analytical and biological fields. This potential stems from the unique properties of cyanostilbenes, such as their AIE characteristic, which sets them apart from other compounds and makes them highly useful for various applications. Further exploration and development of cyanostilbenes could lead to the creation of novel sensing and imaging technologies with wide-ranging applications in both academic and industrial settings

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Section: Sensing Of Sulfitesupporting

confidence: 68%

“…The coumarin pyridinium scaffold with a nitrile group 59 and 60 on the double bond was utilized by our group to detect sulfite through a Michael addition reaction 49 . The molecules are characterized by strong donor moieties, N, N diethylamine, or Julolidine groups, with a pyridinium acceptor.…”

Section: Sensing Of Sulfitementioning

confidence: 99%

Functional α-Cyanostilbenes: Sensing to Imaging

Dahiwadkar

Kaloo

Kanvah³

2023

Synlett

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“…In order to mimic the effects of heat stroke in biological systems, MDA-MB-231 cells treated with PPy-Br (5 μM) were incubated at different temperatures (37,39,41,43, and 45 °C) for 90 min and images were captured (Figure S16a). The fluorescence intensity displayed no change below 39 °C.…”

Section: Heat Stroke Detection In Live Cellsmentioning

confidence: 99%

Cationic Donor–Two-Acceptor Dye–Graphene Quantum Dot Nanoconjugate for the Ratiometric Detection of Bisulfite Ions and Monitoring of SO₂ Levels in Heat-Stressed Cells

Hiremath

Thakuri

Joseph

et al. 2023

ACS Appl. Nano Mater.

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When the body temperature rises above 40.6 °C, heat stress in the cells causes mitochondrial damage. This damage can lead to apoptosis, multiple organ failure, and even death. The dysregulation of SO 2 levels in the mitochondria is linked to this heat stress, and its detection may act as an early indicator of heat stroke. Graphene quantum dots (GQDs), a common class of zerodimensional carbon-based fluorescent nanomaterials, have shown immense potential as sensory probes, and it is a prospective candidate for monitoring SO 2 levels in living cells. Herein, we report a combination of a donor−two acceptor (D2A) red-emissive di-picolinium salt (PPy-Br) and hydroxy-functionalized graphene quantum dots (GQDs-OH) as the fluorescence resonance energy transfer (FRET)-based ratiometric sensor for bisulfite ions detection in aqueous media. The dye-GQD nanoconjugate displays excellent photostability and good aqueous dispersibility allowing the monitoring of SO 2 levels in living cells during heat stress. The PPy-Br:GQD nanoconjugate is indifferent to a large number of cations, anions, or biologically relevant species and displays a detection limit of 36 nM for the solution phase detection of bisulfite. PPy-Br is biocompatible with human cell lines and endocytoses into the cells to ensure monitoring of SO 2 levels in the mitochondrial milieu. PPy-Br-treated human breast cancer cells displayed a gradual decrease in fluorescence at temperatures above 40 °C, indicating an increase in SO 2 levels in heat-stressed cells. The PPy-Br:GQDs sensing conjugate is efficient in the real-time monitoring of intracellular SO 2 levels and demonstrates enough prospects for further explorations as a diagnostic kit for heat stroke monitoring.

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“…The probes showed strong potential for the exo - and endo -genous detection of SO 3 2− in hepatic McA-RH7777 cells with no cytotoxicity. 108 The possible reason for the SO 3 2− detecting mechanism is the strong electron-deficient nature of the pyridinium quaternary cation and the cyano moiety in a single molecular framework makes the CC bond more labile toward the sulfite anions through Michael addition. The sensing mechanism was validated using NMR and mass spectrometry.…”

Section: Chemical Sensingmentioning

confidence: 99%

α-Cyanostilbene: a multifunctional spectral engineering motif

Paramasivam

Kanvah

2022

Phys. Chem. Chem. Phys.

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Cationic red-emitting probes for the rapid and selective detection of SO₂ derivatives in aqueous and cellular environments

Abstract: Reaction based rapid detection of trace quantities of sulfite.

Cited by 30 publications

References 39 publications

Functional α-Cyanostilbenes: Sensing to Imaging

Functional α-Cyanostilbenes: Sensing to Imaging

Cationic Donor–Two-Acceptor Dye–Graphene Quantum Dot Nanoconjugate for the Ratiometric Detection of Bisulfite Ions and Monitoring of SO₂ Levels in Heat-Stressed Cells

α-Cyanostilbene: a multifunctional spectral engineering motif

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Cationic red-emitting probes for the rapid and selective detection of SO2 derivatives in aqueous and cellular environments

Abstract: Reaction based rapid detection of trace quantities of sulfite.

Cited by 30 publications

References 39 publications

Functional α-Cyanostilbenes: Sensing to Imaging

Functional α-Cyanostilbenes: Sensing to Imaging

Cationic Donor–Two-Acceptor Dye–Graphene Quantum Dot Nanoconjugate for the Ratiometric Detection of Bisulfite Ions and Monitoring of SO2 Levels in Heat-Stressed Cells

α-Cyanostilbene: a multifunctional spectral engineering motif

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Cationic red-emitting probes for the rapid and selective detection of SO₂ derivatives in aqueous and cellular environments

Cationic Donor–Two-Acceptor Dye–Graphene Quantum Dot Nanoconjugate for the Ratiometric Detection of Bisulfite Ions and Monitoring of SO₂ Levels in Heat-Stressed Cells