Electrochemistry of a ferrocene-grafted cell-penetrating peptide

Messina, Pierluca; Hallais, Géraldine; Labbé, Éric; Béranger, Marie; Chassaing, Gérard; Lavielle, Solange; Mansuy, Christelle; Buriez, Olivier; Amatore, Christian

doi:10.1016/j.electacta.2012.06.119

Cited by 4 publications

(5 citation statements)

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“…26 For these reasons, it has been widely exploited as an electrochemical tag for the characterization of the electron conduction properties of proteins and peptides. 27 The aim of this work is to prove that peptides comprising two Adt residues: (i) can be stably linked to a gold surface with their main chain parallely-oriented with respect to the substrate and (ii) are able to position tagged probes at a close distance to the surface. The preliminary results of a part of this work have been reported.…”

Section: Introductionmentioning

confidence: 99%

Peptide flatlandia: a new-concept peptide for positioning of electroactive probes in proximity to a metal surface

et al. 2015

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A helical hexapeptide was designed to link in a rigid parallel orientation to a gold surface. The peptide sequence of the newly synthesized compound is characterized by the presence of two 4-amino-1,2-dithiolane-4-carboxylic acid (Adt) residues (positions 1 and 4) to promote a bidentate interaction with the gold surface, two L-Ala residues (positions 2 and 5) and two-aminoisobutyric acid (Aib) residues (positions 3 and 6) to favor a high population of the 310-helix conformation. Furthermore, a ferrocenoyl (Fc) probe was inserted at the N-terminus to investigate the electronic conduction properties of the peptide. X-Ray photoelectron spectroscopy and scanning tunneling microscopy techniques were used to characterize the binding of the peptide to the gold surface and the morphology of the peptide layer, respectively. Several electrochemical (cyclic voltammetry, chronoamperometry, square wave voltammetry) techniques were applied to analyze the electrochemical activity of the Fc probe, along with the influence of the peptide 3D-structure and the peptide layer morphology on electron transfer processes.

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Section: Introductionmentioning

confidence: 99%

Peptide flatlandia: a new-concept peptide for positioning of electroactive probes in proximity to a metal surface

et al. 2015

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“…Though fluorescence-based techniques are the most commonly exploited approaches to detect these peptides [30,31], electrochemical methods may also be of great analytical interest. In this context, we recently reported on the modification of a cationic CPP with a ferrocenyl unit [32]. However, these experiments required large CPP amounts (milliliter electrochemical cell and millimetric sized electrodes).…”

Section: Electrochemical Detection Of a High Value-added Moleculementioning

confidence: 99%

Three-electrode analytical and preparative electrochemistry in micro-volume hanging droplets

Jimenez

Challier

Pisa

et al. 2015

Electrochemistry Communications

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“…In 2012, we established that a cationic CPP could be modified with a redox probe such as ferrocene so as to allow its electrochemical detection. [24] In this work, ferrocene-labelled peptides could be detected at a micromolar concentration, exhibiting the characteristic voltammetric wave of the ferrocene probe. In these conditions, the faradaic signal displayed a poor resolution due to the small diffusion rate of the peptide.…”

Section: Introductionmentioning

confidence: 77%

“…Supported BLMs may afford an adequate electrochemical interface to explore the passage of redox species from the solution to the electrode surface (and vice versa) across the membrane. In 2012, we established that a cationic CPP could be modified with a redox probe such as ferrocene so as to allow its electrochemical detection [24] . In this work, ferrocene‐labelled peptides could be detected at a micromolar concentration, exhibiting the characteristic voltammetric wave of the ferrocene probe.…”

Section: Introductionmentioning

confidence: 96%

Interaction of Redox Probes and Ferrocene‐labelled Peptides with Lipid Bilayers Observed at Lipid Bilayer‐Modified Electrodes

et al. 2021

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Glassy carbon electrodes (GCE) modified by a bilayer of phospholipids (BLM) have been used to monitor the passage of redox probes and ferrocene-labelled peptides across lipid membranes of an anionic (DOPG) or a zwitterionic (globally neutral DPhPC) phospholipid. The gel-phase neutral DPhPC showed a strong association with neutral probes like ferrocene methanol but expelled positively or negatively charged species, as observed on cyclic voltammograms. Anionic DOPG under-went a strong electrostatic interaction with the positively charged hexaamine ruthenium(III) complex, leading to aggregates that caused swelling and destructuration of the BLM. With positively charged ferrocene-tagged peptides, DOPGmodified GCE allowed the observation of cyclic voltammograms exhibiting both a potential shift with respect to bare GCE and increased peak intensity, accounting for the slow but favored partition of the peptides between the BLM and the solution.

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Electrochemistry of a ferrocene-grafted cell-penetrating peptide

Cited by 4 publications

References 50 publications

Peptide flatlandia: a new-concept peptide for positioning of electroactive probes in proximity to a metal surface

Peptide flatlandia: a new-concept peptide for positioning of electroactive probes in proximity to a metal surface

Three-electrode analytical and preparative electrochemistry in micro-volume hanging droplets

Interaction of Redox Probes and Ferrocene‐labelled Peptides with Lipid Bilayers Observed at Lipid Bilayer‐Modified Electrodes

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