Design, synthesis and biological evaluation of a novel Cu 2+ -selective fluorescence sensor for bio-detection and chelation (original) (raw)
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Coumarin-Based Dual Chemosensor for Colorimetric and Fluorescent Detection of Cu2+ in Water Media
A novel coumarin derivative (5) was synthesized and used as a colorimetric and fluorescent probe for selective detection of Cu 2+ ions in the presence of other metal ions, with the detection limits of 5.7 and 4.0 ppb, respectively. Cu 2+ ion reacts with probe 5 to form a 1:1 stoichiometry complex, resulting in a remarkable redshift of absorption maximum from 460 to 510 nm, as well as almost completely quenching fluorescence intensity of probe 5 at the wavelength of 536 nm. These changes can be distinctly observed by naked eyes. In addition, the working pH range of probe 5 is wide and suitable for physiological conditions, thus probe 5 may be used for detection of Cu 2+ ions in living cells. The stable structures of probe 5 and its 1:1 complex with Cu 2+ ion were optimized at the PBE0/6-31+G(d) level of theory. The presence and characteristics of bonds in compounds were studied through atoms in a molecule and natural bond orbital analysis. The formation of the complex led to a strong transfer of electron density from probe 5 as a ligand to Cu 2+ ion, resulting in breaking the π-electron conjugated system, which is the cause of fluorescence quenching and color change of 5-Cu 2+ complex.
Journal of Luminescence, 2018
A potential fluorescent probe, N'-acetyl-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy] acetohydrazide (HMC1) was designed on the basis of photoinduced electron transfer (PET) and synthesized using cheap starting materials. HMC1 was found to be highly efficient as a Cu 2+ ion quencher with a detection limit of 0.64 μM (~ 40 ppb). The binding mode of HMC1 towards Cu 2+ was evaluated by 1 H-NMR, LC-MS and FT-IR techniques. In addition, cellular imaging studies further exhibited that HMC1 could be used an intracellular turn-off fluorescent chemosensor for Cu 2+ in living cells.
Design and synthesis of a new coumarin-based ‘turn-on’ fluorescent probe selective for Cu+2
Tetrahedron Letters, 2012
The novel coumarin-based 'turn-on' fluorescent probe (E)-3-(2,5-dimethoxybenzylideneamino)-7hydroxy-2H-chromen-2-one (MGM) was designed, synthesized, and characterized. This compound shows high selectivity for Cu +2 , combined with a large fluorescence enhancement upon binding to Cu 2+ . Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu 2+ complex formed is 2:1. Preliminary studies employing epifluorescence microscopy demonstrated that Cu +2 could be imaged in human neuroblastoma SH-SY5Y cells treated with MGM.
A highly sensitive and selective fluorescent sensor for Cu 2+ ion in water medium is reported using 4-((benzo[d]thiazol-2ylthio)methyl)-5,7-dihydroxy-2H-chromen-2-one (1) included β-cyclodextrin, as probe. The fluorogenic supramolecule has displayed good selectivity and affinity towards Cu 2+ ions over other cations after examining in biological systems having intracellular Cu 2+ ions, especially in cultured HeLa cells using fluorescence microscopic imaging. The lowest detection limit of Cu 2+ ions observed using this probe is as low as 2.52×10 -10 M. The observed on-off fluorescence with the periodic addition of Cu 2+ ion is explained via an Intramolecular Charge Transfer mechanism (ICT) and the inclusion of 1 in βcyclodextrin is characterised by 1 H-NMR molecular modeling studies. The results show that the present β-CD:1 system, studied in HeLa cells, can be potentially used in monitoring the biological functions of Cu 2+ ions.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019
We have constructed a new coumarin based fluorescence probe BENZPYR with ICT character through condensation of N, N-diethylamino-3-acetyl coumarin with 2hydrazinobenzothiazole. The absorbance and fluorescence spectral characteristics of BENZPYR revealed that the chemosensor can specifically detect for Cu 2+ ions over other different metal ions and the lowest limit of detection was found in nano molar range. The turn off sensor of BENZPYR is related to chelation enhanced quenching (CHEQ) and intramolecular charge transfer (ICT) processes were serve as excellent fluorescent detection of Cu 2+ ions in DMF medium. Fluorescence microscopy experiments revealed that probe BENZPYR may have application as a fluorophore to detect the Cu 2+ in living cells. The simulated DFT analysis of electronic and structural properties and also UV−vis absorption spectra are in well accordance with the experimental UV−vis absorption spectra.
A TPA-caged precursor of (imino)coumarin for “turn-on” fluorogenic detection of Cu+
Analytica Chimica Acta, 2016
In situ formation of (imino)coumarin scaffolds are strategized to achieve reactive fluorogenic probes for Cu þ. The new strategy is verified by a representative CP1 as a probe for fluorescent sensing and imaging of Cu þ. CP1 shows selective "turn-on" fluorescent signal for the detection of Cu þ. CP1 shows low cytotoxicity and can monitor labile copper pools at cellular level.
2012
Department of Chemistry, University of Calcutta, 92, Acharya Prafulla Chandra Road, Kolkata-700 009, India E-mail : ardchem@caluniv .ac. in, ardas66@rediffmail.com Manuscript received 13 September 2011, accepted 16 December 2011 A new series of coumarin based metal ion sensors have been prepared devising a green protocol involving ethyl-(L)-lactate as a polar solvent. These compounds either selectively bind with specific transitional metal ions or form complexes with specific photophysical character when subjected to absorption spectroscopy. The derived Schiff's bases quantitatively bind with metal ions to form 1 : 1 complexes making them a useful tool for qualitative estimation of metal ions in biological as well as organic systems.
Sensors, 2014
Two new coumarin-based "turn-off" fluorescent probes, (E)-3-((3,4dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu 2+ and Fe 3+ ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin (3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10 −5 M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu 2+ and Fe 3+ ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.