Vanillinyl thioether Schiff base as a turn-on fluorescence sensor to Zn2+ ion with living cell imaging

Patra, Chiranjit; Bhanja, Anup Kumar; Sen, Chandana; Ojha, Durbadal; Chattopadhyay, Debprasad; Mahapatra, Ambikesh; Sinha, Chittaranjan

doi:10.1016/j.snb.2016.01.021

Cited by 59 publications

(11 citation statements)

References 48 publications

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“…Herein we report, a diformyl thioether based fluorescent chemosensor, H 2 ‐SAP , prepared by simple Schiff base condensation procedure ( Scheme S1 ) which displays selective fluorescence sensitivity towards Zn 2+ by chelation enhancement fluorescence effect (CHEF) process in presence of large number of ions and could identify Zn 2+ in nM level, much lower than so far reported results . The composition of the complex formed between Zn 2+ and H 2 ‐SAP has been supported by spectroscopic data (Mass, Job's plot) and single crystal X‐ray crystallography.…”

Section: Introductionmentioning

confidence: 70%

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A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

et al. 2019

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3,3′‐((1Z,1′Z)‐(((Propane‐1,3‐diylbis(sulfanediyl))bis(2,1‐phenylene))bis(azanyyldiene))bis(methanylylidene))bis(2‐hydroxy‐5‐methylbenzaldehyde) (H2‐SAP), characterized by different spectroscopic data, exhibits yellow emission (λem, 560 nm) when binds with Zn2+ in H2O‐MeOH (1:9 v/v, HEPES buffer, pH 7.4) in a mixture of seventeen biologically important other metal ions. The limit of detection (LOD) is 9.0 nM which is far below the World Health Organization (WHO) recommended data. The composition of the complex, 1:1 Zn2+:SAP2−, is supported by Job's plot, ESI‐MS and single crystal X‐Ray crystallographic structure. Intracellular Zn2+ ion is detected in Vero Cells (African Green Monkey Kidney) by using the probe, H2‐SAP, in the cell lines under fluorescence microscope. The probe has successfully been applied to recover Zn2+ in surface water.

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Section: Introductionmentioning

confidence: 70%

“…have successfully been used. Our group is also engaged in the design of vanillinyl thioether Schiff base, diformyl thioether Schiff base …”

Section: Introductionmentioning

confidence: 99%

A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

et al. 2019

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“…However, no significant interference is seen ( Figure S15 ) except for Cu 2+ and Fe 3+ ion due paramagnetic quenching of Fe 3+ (d 5 )/ Cu 2+ (d 9 ). The limit of detection (LOD) for Zn 2+ has been calculated for all these sensors and the value lays from 2.2 to 12.3 nM ( Figure S16 ) (using 3σ method) which is far below the WHO recommended value of Zn 2+ in drinking water (76 μM) and are also lower than some reported Schiff base derivatives of Zn 2+ ion sensor ( Table S1 ) . The binding constant also calculated from Benesi–Hildebrand equation ([(F max ‐ F 0 )/(F ‐F 0 )] vs. 1/[ Zn 2+ ]) and the value fall in the range from 3.3 to 7.06 ×10 4 M −1 ( Figure S17 ).…”

Section: Resultsmentioning

confidence: 93%

Effect of ‐OMe Substituent on Salicylaldehyde Schiff Base to Influence the Zn²⁺ Sensitivity and the Cancer Cell Line Imaging

et al. 2019

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Functional group of a molecule monitors the chemical selectivity and the structure regulates the rate of the reaction. Thus, structure‐function relation controls the overall sensitivity of the chemosensor. In this work, three congeneric Schiff bases with common amine, 2,2/‐(propane‐1,2‐diylbis(oxy))dianiline with methoxy substituted Salicylaldehyde are synthesised and have been used to examine the selectivity and sensitivity to the metal ions in 9:1 (v/v) acetonitrile/water (10 mM HEPES buffer, pH 7.4) medium. The probes display prominent fluorescence turn‐on emission when bonded with Zn2+ over sixteen other metal ions with very low limit of detection (LOD), 2.2 to 12.3 nM. Structure with bulkiness has low sensitivity to Zn2+ which may be due to steric crowding about the binding centres of the chelating motif. The selectivity for Zn2+ ion may ascribe to chelation enhancement of fluorescence (CHEF) effect. The probes are characterized by 1H and 13C NMR, IR, HR‐MS and elemental analysis. The metal: ligand ratio of the Zn(II)‐complexes follows 1:1 molar ratio and has been established by Job's plot, Benesi–Hildebrand plot and HR‐MS data. All the probes have been successfully applied to the detection of intracellular Zn2+ ion in Human liver cancer cell line, HepG2.

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“…The association constant (Ka) for Zn 2+ with the probe QS was estimated as 1.36 × 10 4 M −1 from fluorescence titration exploiting the Benesi‐Hildebrand equation (Figure b) . In addition, the detection limits (LOD) of QS towards Zn 2+ was estimated for 2.70 × 10 −8 M based on the definition by 3δ/slope (Figure S5), which met the limit for drinking water according to the WHO standard (46 μM) and pointed to the high detection sensitivity compared with other fluorescent probes. The fluorescence emission changes could be explained that probe QS combined with Zn 2+ reinforced the intramolecular charge transfer (ICT), resulting in red shift of the spectrum, the formation of a rigid structure of the molecule, inhibiting the non‐radiative transition caused by C=N isomerization and the CHEF (chelation enhanced fluorescence effect) process, so that the fluorescence was enhanced.…”

Section: Resultsmentioning

confidence: 99%

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

Chang

Bai

et al. 2019

Applied Organom Chemis

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A novel fluorescent probe 5‐(diethylamino)‐2‐(((2‐(hydroxymethyl)quinolin‐8‐yl)imino)methyl)phenol (QS) was synthesized by condensation reaction of 8‐aminoquinoline derivative and 4‐(diethylamino)salicylaldehyde. It was found that the probe QS was capable of high selectivity and sensitivity about specific color and fluorescence changes towards Zn2+ ion in EtOH‐H2O (v/v = 4/1, 0.01 M, Tris–HCl buffer, pH = 7.30) solution. The interaction of QS with Zn2+ ion illustrated a “turn‐on” fluorescence response at 550 nm (λex: 458 nm), moreover, after the subsequent addition of inorganic phosphate (Pi) into the solution above, a “turn‐off” fluorescence response was observed. The sensing ability of the probe QS towards Zn2+ was confirmed by fluorescence titration, UV–Vis titration and HRMS analysis. Besides, the intracellular sensing behavior of QS with Zn2+ and Pi were captured in living PC12 cells. The limit of detection (LOD) for Zn2+ and Pi sensing was found to be 0.03 μM and 0.08 μM, respectively.

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Vanillinyl thioether Schiff base as a turn-on fluorescence sensor to Zn2+ ion with living cell imaging

Cited by 59 publications

References 48 publications

A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

Effect of ‐OMe Substituent on Salicylaldehyde Schiff Base to Influence the Zn²⁺ Sensitivity and the Cancer Cell Line Imaging

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

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Vanillinyl thioether Schiff base as a turn-on fluorescence sensor to Zn2+ ion with living cell imaging

Cited by 59 publications

References 48 publications

A Phenyl Thioether‐Based Probe: Zn2+ Ion Sensor, Structure Determination and Live Cell Imaging†

A Phenyl Thioether‐Based Probe: Zn2+ Ion Sensor, Structure Determination and Live Cell Imaging†

Effect of ‐OMe Substituent on Salicylaldehyde Schiff Base to Influence the Zn2+ Sensitivity and the Cancer Cell Line Imaging

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

Contact Info

Product

Resources

About

A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

A Phenyl Thioether‐Based Probe: Zn²⁺ Ion Sensor, Structure Determination and Live Cell Imaging^†

Effect of ‐OMe Substituent on Salicylaldehyde Schiff Base to Influence the Zn²⁺ Sensitivity and the Cancer Cell Line Imaging