Dual ion selective fluorescence sensor with potential applications in sample monitoring and membrane sensing

Kumawat, Lokesh Kumar; Asif, Mohammad; Gupta, Vinod Kumar

doi:10.1016/j.snb.2016.10.031

Cited by 16 publications

(7 citation statements)

References 54 publications

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“…Much of the literature surrounding anion sensors relies on a binding event that disrupts/enhances some type of electron transfer mechanism such as photoinduced electron transfer (PET), internal charge transfer (ICT), excited state intramolecular proton transfer (ESIPT), fluorescence resonance energy transfer (FRET), etc. to yield a measurable fluorescence response (de Silva et al, 1997; Wu et al, 2011; Fan et al, 2013; Lee et al, 2015; Kumawat et al, 2017; Sedgwick et al, 2018). Some more recent reports take advantage of aggregation induced emission (AIE) (Hong et al, 2011), whereby recognition of an anion causes aggregation of the sensor thereby reducing molecular rotation and inducing large fluorescence perturbations (Peng et al, 2009; Ma et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Squaramide—Naphthalimide Conjugates as “Turn-On” Fluorescent Sensors for Bromide Through an Aggregation-Disaggregation Approach

et al. 2019

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The syntheses of two new squaramide-naphthalimide conjugates ( SQ1 and SQ2 ) are reported where both compounds have been shown to act as selective fluorescence “turn on” probes for bromide in aqueous DMSO solution through a disaggregation induced response. SQ1 and SQ2 displayed a large degree of self-aggregation in aqueous solution that is disrupted at increased temperature as studied by 1 H NMR and Scanning Electron Microscopy (SEM). Moreover, the fluorescence behavior of both receptors was shown to be highly dependent upon the aggregation state and increasing temperature gave rise to a significant increase in fluorescence intensity. Moreover, this disaggregation induced emission (DIE) response was exploited for the selective recognition of certain halides, where the receptors gave rise to distinct responses related to the interaction of the various halide anions with the receptors. Addition of F − rendered both compounds non-emissive; thought to be due to a deprotonation event while, surprisingly, Br − resulted in a dramatic 500–600% fluorescence enhancement thought to be due to a disruption of compound aggregation and allowing the monomeric receptors to dominate in solution. Furthermore, optical sensing parameters such as limits of detection and binding constant of probes were also measured toward the various halides (F − , Cl − , Br − , and I − ) where both SQ1 and SQ2 were found to sense halides with adequate sensitivity to measure μM levels of halide contamination. Finally, initial studies in a human cell line were also conducted where it was observed that both compounds are capable of being taken up by HeLa cells, exhibiting intracellular fluorescence as measured by both confocal microscopy and flow cytometry. Finally, using flow cytometry we were also able to show that cells treated with NaBr exhibited a demonstrable spectroscopic response when treated with either SQ1 or SQ2 .

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Section: Introductionmentioning

confidence: 99%

Squaramide—Naphthalimide Conjugates as “Turn-On” Fluorescent Sensors for Bromide Through an Aggregation-Disaggregation Approach

et al. 2019

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“…S1). The dissociation constant (K d ) of this complex, as derived from the uorescence titration data using Benesi-Hildebrand equation [28,29], was 5.4 x 10 -6 mol L -1 (Fig. S2).…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of 3,3-bis(methylsulfanyl)-1-(pyridin-2-yl)prop-2-en-1-one (1) (225 mg, 1 mmol) [26] in pyridine (5 mL), guanidine carbonate (2) (270 mg, 1.5 mmol) was added and the mixture was re uxed for 5 h. The reaction mixture was poured into 100 mL of ice water, and the precipitate was collected by ltration, washed with water, and dried overnight. The product was recrystallized from methanol to give Benesi-Hidebrand plot [28,29].…”

Section: Synthesis Of 4-(methylsulfanyl)-6-(pyridin-2-yl)pyrimidin-2-amine (3)mentioning

confidence: 99%

Selective Cadmium Fluorescence Probe Based on Bis-heterocyclic Molecule and its Imaging in Cells

et al. 2021

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Fluorescence probes that selectively image cadmium are useful for detecting and tracking the amount of Cd 2+ in cells and tissues. In this study, we designed and synthesized a novel Cd 2+ uorescence probe based on the pyridine-pyrimidine structure, 4-(methylsulfanyl)-6-(pyridin-2-yl)pyrimidin-2-amine (3), as a low-molecular-weight uorescence probe for Cd 2+ . Compound could successfully discriminate between Cd 2+ and Zn 2+ and exhibited a highly selective turn-on response toward Cd 2+ over biologically related metal ions. The dissociation constant and detection limit of 5.4 x 10 − 6 mol L − 1 and 4.4 × 10 − 7 mol L − 1 , respectively, were calculated using uorescence titration experiments. Studies with closely related analogs showed that the bis-heterocyclic moiety of acted as both a coordination site for Cd 2+ and a uorophore. Further, the methylsulfanyl group of compound is essential for achieving selective and sensitive Cd 2+ detection. Fluorescence microscopy studies using living cells revealed that the cell membrane permeability of compound is su cient to detect intracellular Cd 2+ . These results indicate that novel bis-heterocyclic molecule has considerable potential as a uorescence probe for Cd 2+ in biological applications.

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“…Job’s plot was used to investigate the binding stoichiometries of 3a,b , 4a,b , and 5a,b to Zn 2+ . The dissociation constant ( K d ) values were investigated by the following Benesi–Hildebrand plot [19,20]. 1/( F – F 0 ) = 1/{ K a ( F max – F 0 )[Zn 2+ ] n } + 1/( F max – F 0 ) where F is the fluorescence intensity, F 0 is the fluorescence intensity without Zn 2+ , and F max is the fluorescence in addition of excess Zn 2+ .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of a Novel Pyrazine–Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells

Hagimori

Taniura

Mizuyama

et al. 2019

Sensors

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A small extent of endogenous labile zinc is involved in many vital physiological roles in living systems. However, its detailed functions have not been fully elucidated. In this study, we developed a novel biheteroaryl-based low molecular weight fluorescent sensor, 3-(phenylsulfonyl)-pyrazine–pyridone (5b), and applied it for the detection of endogenous labile zinc ions from lung cancer cells during apoptosis. The electron-withdrawing property of the sulfonyl group between the phenyl ring as an electron donor and the pyridone ring as a fluorophore inhibited the intramolecular charge transfer state, and the background fluorescence of the sensor was decreased in aqueous media. From the structure–fluorescence relationship analysis of the substituent effects with/without Zn2+, compound 5b acting as a sensor possessed favorable properties, including a longer emission wavelength, a large Stokes shift (over 100 nm), a large fluorescence enhancement in response to Zn2+ under physical conditions, and good cell membrane permeability in living cells. Fluorescence imaging studies of human lung adenocarcinoma cells (A549) undergoing apoptosis revealed that compound 5b could detect endogenous labile zinc ions. These experiments suggested that the low molecular weight compound 5b is a potential fluorescence sensor for Zn2+ toward understanding its functions in living systems.

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Dual ion selective fluorescence sensor with potential applications in sample monitoring and membrane sensing

Cited by 16 publications

References 54 publications

Squaramide—Naphthalimide Conjugates as “Turn-On” Fluorescent Sensors for Bromide Through an Aggregation-Disaggregation Approach

Squaramide—Naphthalimide Conjugates as “Turn-On” Fluorescent Sensors for Bromide Through an Aggregation-Disaggregation Approach

Selective Cadmium Fluorescence Probe Based on Bis-heterocyclic Molecule and its Imaging in Cells

Synthesis of a Novel Pyrazine–Pyridone Biheteroaryl-Based Fluorescence Sensor and Detection of Endogenous Labile Zinc Ions in Lung Cancer Cells

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