Intracellular application and logic gate behavior of a ‘turn off-on-off’ type probe for selective detection of Al3+ and F− ions in pure aqueous medium (original) (raw)
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A naphthalene based sulfonamide Schiff base, (E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-N-(5methylisoxazol-3-yl)benzenesulfonamide (HL) has been found to be a flourescence turn-on probe for selective detection of Al 3+ in aqueous system. Structure of the probe has been established by FTIR, 1 H NMR, mass spectra and X-ray single crystal study. The probe has shown 24 times flourescence enhancement in presence of Al 3+ . The limit of detection (LOD) obtained by 3s method is 33.2 nM. The probable co-ordination environment of L-Al 2+ complex has been supported by mass spectral data and DFT computational study. By TD-DFT calculation UV-Vis spectra of HL and L-Al 2+ complex has been predicted and that has well correlated with experimental data. Cell imaging study reveals that the probe can be used for the intracellular detection of Al 3+ in cultured Vero cell. Antimicrobial activity of HL has also been evaluated and probable mode of binding inside the DHPS cavity has been predicted by docking study. This sensor is unique with reference to two other predecessors because of its biocompatibility of sulfonamide derivative and nonmutagenicity.
Journal of Luminescence, 2019
A new 2-hydroxynaphthalen based Schiff base colorimetric and fluorescence chemosensor, H 2 L {(E)-4-((2-hydroxynaphthalen-1-yl)methyleneamino)benzoic acid}, for selective sensing of Al 3+ ions has been synthesized and characterize by different physico-chemical and spectroscopic techniques. The probe shows enhanced fluorescence and significant color change from bright yellow to colorless in the presence of Al 3+ ions in methanol-water (9:1 v/v) solution, without interference from other metal ions. The binding mode of H 2 L with Al 3+ was studied by UV-vis, fluorescence titration, job's plot analysis, and ESI-MS. The probe acts as a bidentate ligand and interacts with Al 3+ ions with a binding constant of K b = 1.546 × 10 5 M-1. The limit of detection for Al 3+ is found to be 6.4 × 10 −7 M. The cytotoxicity of the probe has been evaluated by MTT assay on MCF-7 cell line, indicating more than 92% cell viability in the concentration range of 1.25-50 μM with no serious cytotoxicity on cells. Live cell imaging study clearly indicates that the 2 accumulation of Al 3+ in living cells can be detected by H 2 L.
A simple and smart chemosensor (DSA) has been developed using Schiff base ligand for highly sensitive and selective colorimetric detection of Al 3 + / Cu 2 + in partial aqueous DMSO mixture (1:1) as a solvent medium. It showed a rapid fluorescence response (~ 10 Sec) with Al 3 + as greenish yellow from weak orange fluorescence while, Cu 2 + ions affords yellow colour from fade orange colour and it can be sensed even by naked eyes. Besides showing great selectivity, the probe gives a lower sensitivity of 20 nM for Al 3 + and 0.27 mM for Cu 2 + in the fluorescence and UV-vis. spectral studies respectively. The solid state colorimetric and fluorescence changes of the probe were examined in silica supported TLC plates. The sensing mechanism of the proposed probe in the presence of Al 3 + and Cu 2 + was determined with the support of a job's plot, 1 H-NMR, ESI-Mass and theoretical (DFT) analysis. Based on the observed results from the absorbance and fluorescence spectroscopic studies, a logic circuit was designed with the combination of OR, NOT and AND logic gates. Moreover, the probe DSA has been employed for live cell imaging to detect Al 3 + ions in C6 glioma cells and it showed a good cell permeability and efficiency in the detection of Al 3 + ions.
Acta Chimica Slovenica
Six different Schiff bases to be used as turn-on fluorescent probes based on photoinduced electron transfer (PET) mechanism for the recognition of aluminum ions were successfully synthesized and characterized. The binding abilities of synthesized compounds with different metal cations were investigated by absorption and emission spectra. From the spectrophotometric experiments, it were seen that compound SK-1 displayed an excellent fluorescence response towards targeted aluminum ions probably due to its suitable chelating structure. Furthermore, such compound SK-1 also showed high sensitivity and selectivity response towards aluminum ions over other competing ions. In addition, the potential biological applications of SK-1 to detect aluminum ions in living cells were also investigated and results showed that fluorescence sensor SK-1 could be a promising probe for determining and/or monitoring aluminum ions in both biological and/or chemical samples.
Inorganica Chimica Acta, 2017
The interaction of L with Al 3+ results bright blue fluorescence under UV radiation and the fluorescence intensity enhances by ca. 40 times. The 1:1 interaction between L and Al 3+ has been established from spectroscopic data as well as from DFT calculations. Snapping of photo induced electron transfer (PET) prevailed in L, due to interaction with Al 3+ , is responsible for the fluorescence intensity enhancement. The detection limit and binding constant of L towards Al 3+ is 10-5 M and 10 5.14 M-1 respectively. L is applicable for determination of Al 3+ in bovine serum albumin and for live cell imaging. The Al 3+ :L complex acts as PO 4 3ion sensor by fluorescent "on-off" mode over the anions-F-, Br-, I-, NO 3-, HF 2-, SCN-, CH 3 COOand HCO 3 2-.L is found to exhibit INHIBIT logic gate behaviour with PO 4 3and Al 3+ as inputs.
A probe, quinoline-2-carboxylic acid (4-oxo-4H-chromen-3-ylmethylene)-hydrazide, (HL), acts as selective and specific fluorogenic sensor to Al +3 in the visible light (435 nm) excitation in presence of biologically available large number of cations and emission appears at (em) 520 nm. The limit of detection (LOD) for Al +3 is 7.6 nM in aqueous medium which is less than 10 −3 times of WHO recommended data (7.41 mM). The Job's plot and mass spectral data support 1:1 composition of the complex [Al(HL)(OH)H 2 O](NO 3) 2. The strongly emissive complex turns off upon addition of F − and is detected at the level of (LOD) 7.4 nM. Thus, F − , a harmful water pollutant, could be identified at much lower level of WHO recommended toxic limit (3.68 M). The absorption and emission spectral features of HL and its Al +3-complex have been explained by DFT computation of optimized geometries and calculation of molecular functions. The devised receptor is non-toxic and has been used in detecting Al +3 in the intra-cellular region of African green monkey kidney cells (Vero cells) and exhibits an INHIBIT logic gate with Al +3 and F − as chemical inputs by monitoring the emission mode at 520 nm.
Inorganica Chimica Acta, 2014
The well known rhodamine framework offers an ideal model for the development of fluorescence enhanced chemosensors. Herein, a novel and simple molecule chemosensor, (E)-2-((benzo[d][1,3] dioxol-4-ylmethylene)amino)-3 0 ,6 0-bis(diethylamino)spiro[isoindoline-1,9 0-xanthen]-3-one (L), has been designed by combining a rhodamine B hydrazide and a benzo[d][1,3]dioxole-4-carbaldehyde in a single molecule to prove the selectivity and sensitivity for Al 3+ and Cr 3+ in a dual-channel mode (fluorescence emission and UV-Vis). The signal transduction occurred by the increase of conjugation in the ring-open form than in the ring-closed form. Furthermore, the chemosensor L could also be used as an imaging probe without cytotoxicity for uptake and detection of Al 3+ ion in HeLa cells.
Analyst, 2012
2-((Naphthalen-6-yl)methylthio)ethanol (HL) was prepared by one pot synthesis using 2mercaptoethanol and 2-bromomethylnaphthalene. It was found to be a highly selective fluorescent sensor for Al 3+ in the physiological pH (pH 7.0-8.0). It could sense Al 3+ bound to cells through fluorescence microscopy. Metal ions like Mn 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Ag + , Cd 2+ , Hg 2+ , Cr 3+ and Pb 2+ did not interfere. No interference was also observed with anions like Cl À , Br À , F À , SO 4 2À , NO 3 À , CO 3 2À , HPO 4 2À and SCN À . Experimentally observed structural and spectroscopic features of HL and its Al 3+ complex have been substantiated by computational calculations using density functional theory (DFT) and time dependent density functional theory (TDDFT).
ChemistryOpen, 2015
The development of novel selective probes with high sensitivity for the detection of Al(3+) is widely considered an important research goal due to the importance of such probes in medicine, living systems and the environment. Here, we describe a new fluorescent probe, N'-(4-diethylamino-2-hydroxybenzylidene)-2-hydroxybenzohydrazide (1), for Al(3+). Probe 1 was evaluated in a solution of acetonitrile/water (1:1 v/v). Compared with previously reported probes for Al(3+), probe 1 can be synthesized easily and in high yield. A Job plot confirmed that probe 1 is able to complex Al(3+) in a 1:1 ratio, and the binding constant was determined to be 4.25×10(8) m(-1). Moreover, the detection limit was as low as 6.7×10(-9) m, suggesting that probe 1 has a high sensitivity. Common coexistent metal ions, such as K(+), Co(2+), Ca(2+), Ba(2+), Ni(2+), Pb(2+), Hg(2+), Ce(2+), Zn(2+), Cd(2+), Fe(3+), showed little or no interference in the detection of Al(3+) in solution, demonstrating the high s...
ACS Omega
The synthesized Schiff base ligand 3-hydroxy-N′-(2hydroxy-3-methoxybenzylidene)-2-naphthohydrazide (H 2 NPV) is structurally characterized by single-crystal X-ray diffraction (XRD) and exhibits weak fluorescence in the excited state owing to the effect of excited-state-induced proton transfer (ESIPT). However, in the presence of Al 3+ , the ESIPT is blocked and chelation-enhanced fluorescence (CHEF) is induced because of complexation with the cations, resulting in turn-on emission for Al 3+. The probe H 2 NPV selectively detects Al 3+ among the various metal ions, and the detection limit is found to be 1.70 μM. The composition and modes of complex coordination were determined by spectroscopic, theoretical studies and molecular logic gate applications. Finally, DNA binding studies were performed by spectroscopic and calorimetric methods to elucidate possible bioactivity of H 2 NPV.