Pyridoxal Based Fluorescent Chemosensor for Detection of Copper(II) in Solution With Moderate Selectivity and Live Cell Imaging (original) (raw)
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Sensors and Actuators B: Chemical, 2014
The commercially available 2, 3-diaminophenazine, 1, 2-diamino-anthraquinone and 2, 4dinitrophenylhydrazine (S1-S3) act as a colorimetric, fluorescent probes for selective detection of Cu 2+ ions in aqueous medium over other metal ions. In presence of Cu 2+ , S1 shows fluorescent turn-off by the paramagnetic effect. S2 and S3 with Cu 2+ ions show fluorescent turn-on due to the inhibition of photoinduced electron transfer mechanism. The fluorescent probes S1-S3 detect Cu 2+ ions in aqueous solution at nanomolar levels. Theoretical calculations were employed to understand the sensing mechanism of the sensors towards Cu 2+. S1, S2 and S3 were further applied for biological imaging to confirm that it can be used as a fluorescent probe for monitoring Cu 2+ in living cells, and demonstrated its value in practical applications such as environmental and biological systems.
Selective fluorescence detection of Cu2+ in aqueous solution and living cells
Journal of Luminescence, 2014
A rhodamine B semicarbazide 3 was synthesized by the reaction of rhodamine B acid chloride 2 with hydrazine carboxamide hydrochloride under reflux with triethyl amine in acetonitrile. It was used as selective fluorescent and colorimetric sensor for visual detection of Cu 2 þ over competitive ions (Fe 3 þ , Fe 2 þ , Cr 3 þ , Cd 2 þ , Pb 2 þ , Zn 2 þ , Hg 2 þ , Co 2 þ , Ni 2 þ , Ca 2 þ , Mg 2 þ , Ag 2 þ , Mn 2 þ , Sr 2 þ , Cs 2 þ , Na þ , K þ , Li þ ) in aqueous methanol (1:1, v/v), exhibiting a fast response time, less than few second and a detection limit of 1.6 Â 10 À 7 mol/L at neutral pH. The proposed sensing system can be successfully applicable for determination of Cu 2 þ in waste water samples showing turn on fluorescence response and for further monitoring of intracellular Cu 2 þ levels in living cells with high sensitivity and selectivity at micro molar level concentrations using confocal fluorescence spectroscopy. The synthesis of probe 3 was confirmed by 1 H NMR, 13 C NMR and mass spectrometric analysis.
A novel fluorescent chemosensor 9,10-Diphenyl-7H-benzo [d,e]imidazo[2,1-a]isoquinolin-7-one (BIDQ-1), which exhibits rapid colorimetric and fluorimetric response for copper ions over other competitive metal ions under mild conditions has been synthesized easily by a simple one pot condensation method. On addition of Cu(II), BIDQ-1 shows a distinct color change from yellow to green, thus permitting the probe to be used for naked eye detection of Cu(II). The new fluorescent probe exhibits a turn-on fluorescence response towards Cu 2+ under physiological conditions with high sensitivity and selectivity. The turn-on fluorescence behaviour of BIDQ-1 with Cu(II) was found to be via an intramolecular charge transfer (ICT) mechanism, by TD-DFT calculations. The probe was found to be applicable for imaging intracellular Cu 2+ in living cells.
Dalton Transactions
A new thioimidazole derivative of coumarin appended with salicylyl imine (L) has been synthesized and characterized. The L has been found to selectively recognize Cu2+ among the biologically relevant metal ions studied. The chemosensing behavior of the L has been demonstrated through fluorescence, absorption, visual fluorescent color changes, ESI MS and 1H NMR titrations. The chemosensor L showed selectivity toward Cu2+ by switch on fluorescence among the 14 metal ions studied with a detection limit of 1.5 µM. The complex formed between L and Cu2+ is found to be 1:1 on the basis of absorption and fluorescence titrations and was confirmed by ESI MS. DFT and TDDFT calculations were performed in order to demonstrate the structure of L and [CuL] and electronic properties of chemosensor L and their copper complex. This highly fluorescing [CuL] complex has been used to recognize sulphide selectively among the other allied anions. Microstructural features of L and its Cu2+ complex have bee...
Dalton Transactions
A new coumarin-appended thioimidazole-linked imine conjugate, viz. L has been synthesized and characterized. The L has been found to 10 recognize Cu2+ selectively among a wide range of biologically relevant metal ions. The chemosensing behavior of the L has been demonstrated through fluorescence, absorption, visual fluorescent color changes, ESI-MS and 1H NMR titrations. The chemosensor L showed selectivity toward Cu2+ by switch on fluorescence among the metal ions studied with a detection limit of 1.53 μM. The complex formed between L and Cu2+ is found to be 1:1 on the basis of absorption and fluorescence titrations and was confirmed by ESIMS. DFT and TDDFT calculations were performed in order to demonstrate the structure of L and [CuL] and electronic properties of chemosensor L and their copper complex. This highly fluorescent [CuL] complex has been used to recognize sulphide selectively among the other allied anions. Microstructural features of L and its Cu2+ complex have been in...
Journal of Photochemistry and Photobiology A: Chemistry, 2018
A new pyrene based chemosensor 1 exhibited high selectivity towards Copper (II) ions, with live cell imaging. Highlights The conveniently Pyrene motif Schiff base derivative was designed and synthesized. The chemosensor exhibited enhanced fluorescence intensity in the presence of Cu 2+ ions in human physiological conditions. The stoichiometric ratio between chemosensor 1 and Cu 2+ were examined by Job's plot method.
RSC Advances, 2013
A new turn-on Cu 2+ fluorescent sensor (CST) having a trehalose moiety, which confers a relatively large solubility in water, has been synthesized. The chemosensor is therefore suitable for studies in aqueous solution. Full potentiometric and UV-vis characterization evidence that at physiological pH CST forms with Cu 2+ a species with a 1 : 1 stoichiometry allowing for a straightforward correlation between CST response and copper(II) concentration. The presence of the trehalose unit does not negatively affect the selectivity of CST for Cu 2+ over a series of metal ions of interest as proven by fluorescence measurements. The novel chemosensor, tested in differentiated neuroblastoma SH-SY5Y cells, is able to detect Cu 2+ in the extracellular region, as well as to track copper transfer processes upon cell stimulation induced by cellular depolarization. ; Fax: +39 051 20 9 9456; Tel: +39 051 20 9 9481 † Electronic supplementary information (ESI) available: NMR spectra, species distribution diagram of the proton complexes of CST, UV-vis of CST, inuence of the pH on the uorescence emission of CST and uorescence response of CST to some selected anions. See
Tetrahedron Letters, 2010
Schiff base sensor 1, containing naphthalene and naphthalimide fluorophores with separate and distinct emission wavelengths, showed good selectivity for Cu(II) over other tested physiological and environmentally important cations through changes in its fluorescence spectra in THF/H 2 O (9:1) HEPES buffered solution. By taking the ratiometric change of the emissions at 435 nm (naphthalene-Schiff base) and 510 nm (naphthalimide) good linearity was observed in the 0-10 lM range. The enhancement of the 435 nm emission upon binding Cu 2+ was attributed to a prevention of the rapid C@N isomerisation that otherwise leads to non-radiative decay, while the quenching of the naphthalimide emission was attributed to electron transfer between the excited naphthalimide fluorophore and the redox active Cu 2+ .
Chemosensors play important roles in cation and anion recognition in biological, industrial, and environmental processes. Although many efforts have been made to develop artificial fluorescent receptors for Cu2+ and S2−, their applications in the detection in bulk solutions are limited. In this work, we report a novel fluorescence chemosensor (NL) based on the 7-nitrobenz-2-oxa-1,3-diazole (NBD) fluorophore for the quantification of Cu2+ and S2− in single intact cells. NL specifically binds to Cu2+ in the presence of other competing cations, and evident changes in UV-vis and fluorescence spectra in HEPES buffer are noticed. Based on the displacement approach, the selective sense S2− with the in situ generated NL-Cu2+ ensemble gives a remarkable recovery of fluorescence and UV-vis absorption spectra. The detection limits of NL for Cu2+ and NL-Cu2+ for S2− were estimated to be 1.6 nM and 0.17 μM, respectively. NL and the resultant complex NL-Cu2+ exhibit low cytotoxicity and cell-membrane permeability, which makes them capable of Cu2+ and S2− imaging and quantification in living MDA-MB-231 cells.