An Impedimetric Sensor Based on a Gold Electrode Functionalized with a Thiol Self‐Assembled Monolayer Modified by Terpyridine Ligands for the Detection of Free Gadolinium Ions

Mefteh, Wahid Ben; Touzi, Hassen; Bessueille, François; Chevalier, Yves; Kalfat, Rafik; Jaffrézic‐Renault, Nicole

doi:10.1002/elan.201400373

Cited by 9 publications

(6 citation statements)

References 32 publications

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“…Terpyridine forms coordination chelates of the tridentate pincer (claw-shaped) type, due to the presence of three conjugated nitrogen atoms in the molecule [ 21 , 22 ]. Tpy can provide stable chelation with various metal cations, including large-radius metal ions (e.g., Gd(III)), in an almost flat geometry [ 23 , 24 ]. The combination of two heterocycles, namely, porphyrins and terpyridines, makes them suitable for various photobiological applications, because of the valuable photophysical and coordination properties of the resulting conjugates.…”

Section: Introductionmentioning

confidence: 99%

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

et al. 2023

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This paper reports on the design and synthesis of new multifunctional porphyrin-based therapeutic agents for potential therapeutic and diagnostic applications. Zinc complexes of A3B-type meso-arylporphyrins containing OH- and COOH- groups were modified with chelating ligands based on 4′-(4-methylphenyl)-2,2′:6′,2″-terpyridine derivatives in high yields. Novel complexes with Gd(III), Fe(III) were obtained for these conjugates. Aggregation behaviour in solutions of different solubilisers was studied to inform the selection of the optimal solubilising platform for the porphyrins obtained; their photophysical and photochemical properties were also characterised. Micellar Pluronic F127 formulation was found to be the most effective solubiliser for stabilising the fluorescence-active monomolecular form of the photosensitisers (PS). In vitro cytotoxicity of the compounds was studied on the HEP-2 cell line with and without irradiation for 1.5 and 24 h. As a result, the IC50 of compounds 12 and 14 at an irradiation dose of 8.073 J/cm2 was shown to be 1.87 ± 0.333 and 1.4 ± 0.152 μM, respectively; without irradiation, the compound had no toxic effect within the studied concentration range (1.5 h). A test for the inhibition of metabolic cooperation or promoter activity was also performed for the abovementioned compounds, showing the efficacy and safety of the conjugates obtained. Preliminary data have indicated the high potential of the new type of PS to be promising molecular theranostic agents.

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Section: Introductionmentioning

confidence: 99%

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

et al. 2023

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“…Voltammetric detection of gadolinium was achieved by the impregnation of nano-sized Gd(III)-imprinted polymer in carbon paste electrodes [ 33 ]. Impedimetric detection of gadolinium was obtained by the modification of gold electrodes with terpyridine ligands [ 34 ]. In this work, 2-methylpyridine-substituted cyclam (bis-N-MPyC) as a tetraazamacrocycle was used as a recognition molecule for the detection of gadolinium.…”

Section: Introductionmentioning

confidence: 99%

Detection of Gadolinium with an Impedimetric Platform Based on Gold Electrodes Functionalized by 2-Methylpyridine-Substituted Cyclam

Touzi

Chevalier

Martin

et al. 2021

Sensors

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Gadolinium is extensively used in pharmaceuticals and is very toxic, so its sensitive detection is mandatory. This work presents the elaboration of a gadolinium chemical sensor based on 2-methylpyridine-substituted cyclam thin films, deposited on gold electrodes, using electrochemical impedance spectroscopy (EIS). The 2-methylpyridine-substituted cyclam (bis-N-MPyC) was synthesized in three steps, including the protection of cyclam by the formation of its CH2-bridged aminal derivative; the product was characterized by liquid 1H and 13C NMR spectroscopy. Spin-coated thin films of bis-N-MPyC on gold wafers were characterized by means of infrared spectroscopy in ATR (Attenuated Total Reflectance) mode, contact angle measurements and atomic force microscopy. The impedimetric chemical sensor was studied in the presence of increasing concentrations of lanthanides (Gd3+, Eu3+, Tb3+, Dy3+). Nyquist plots were fitted with an equivalent electrical circuit including two RC circuits in series corresponding to the bis-N-MPyC film and its interface with the electrolyte. The main parameter that varies with gadolinium concentration is the resistance of the film/electrolyte interface (Rp), correlated to the rate of exchange between the proton and the lanthanide ion. Based on this parameter, the detection limit obtained is 35 pM. The bis-N-MPyC modified gold electrode was tested for the detection of gadolinium in spiked diluted negative urine control samples.

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“…They have been investigated for their potential applications in materials research, polymer science, nanotechnology, catalysis, medicine, and light-to-energy conversion. [2][3][4][5][6][7][8] Among the various terpyridine ligands, a few coumarincontained terpyridines and/or their complexes have been reported to exhibit prominent properties and are used as fluorescent chemosensors or molecular energy transfer switch. [9][10][11] In recent years, we have been engaging in the synthesis of novel coumarin derivatives and investigation of their fluorescent properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel coumarin-based terpyridine ligands and their Zn(II) complexes

Wang

Yue

Deng

2020

Journal of Chemical Research

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Two novel mononuclear Zn(II) complexes, [ZnL1Cl2] (1) (L1=( E)-3-(4-(2,2′:6′,2″-tripyridyl)-4′-styryl)-7-diethylaminocoumarin) and [ZnL2Cl2] (2) (L2=3-(4-(2,2′:6′,2″-tripyridyl)-4′-phenylimine)-7-diethylaminocoumarin), were obtained by the solvothermal method from ZnCl2 and coumarin-based terpyridine ligands. The complexes were characterized by spectroscopic methods and single-crystal X-ray diffraction. The Zn2+ in the complexes is coordinated by three nitrogen atoms of the terpyridine ligand and two chloride anions, forming a distorted trigonal bipyramidal environment. Moreover, the UV–Vis absorption and emission spectra of the ligands and complexes in diluted dichloromethane solutions were measured.

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An Impedimetric Sensor Based on a Gold Electrode Functionalized with a Thiol Self‐Assembled Monolayer Modified by Terpyridine Ligands for the Detection of Free Gadolinium Ions

Cited by 9 publications

References 32 publications

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

Design of A3B-Porphyrin Conjugates with Terpyridine as Potential Theranostic Agents: Synthesis, Complexation with Fe(III), Gd(III), and Photodynamic Activity

Detection of Gadolinium with an Impedimetric Platform Based on Gold Electrodes Functionalized by 2-Methylpyridine-Substituted Cyclam

Synthesis and characterization of novel coumarin-based terpyridine ligands and their Zn(II) complexes

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