The versatility of pyrene and its derivatives on sp2 carbon nanomaterials for bioelectrochemical applications

Holzinger, Michael; Cosnier, Serge; Buzzetti, Paulo Henrique M.

doi:10.1016/j.synthmet.2022.117219

Cited by 10 publications

(3 citation statements)

References 58 publications

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“…40,41 Specifically, pyrene and its analogues can π-stack onto graphene and carbon nanotubes. 42 This approach was first leveraged to create self-assembled layers of nucleic acid aptamers onto fluorescence resonance energy transfer-based sensors (FRETs). 43 The resulting sensors achieved continuous molecular monitoring inside a flow chamber over measurement periods of minutes (Figure 2B).…”

Section: ■ Strategies Based On Self-assemblymentioning

confidence: 99%

“…Carbon probes are already in use for electrophysiological and neurotransmitter measurements in the brain, but have not been extensively used for affinity-based continuous molecular monitoring. Here, I highlight the use of the anchoring group pyrene to self-assemble oligonucleotides on carbon electrodes (Figure A). , Specifically, pyrene and its analogues can π-stack onto graphene and carbon nanotubes . This approach was first leveraged to create self-assembled layers of nucleic acid aptamers onto fluorescence resonance energy transfer-based sensors (FRETs) .…”

Section: Strategies Based On Self-assemblymentioning

confidence: 99%

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Beyond the Gold–Thiol Paradigm: Exploring Alternative Interfaces for Electrochemical Nucleic Acid-Based Sensing

Arroyo-Currás

2024

ACS Sens.

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Nucleic acid-based electrochemical sensors (NBEs) use oligonucleotides as affinity reagents for the detection of a variety of targets, ranging from small-molecule therapeutics to whole viruses. Because of their versatility in molecular sensing, NBEs are being developed broadly for diagnostic and biomedical research applications. Benchmark NBEs are fabricated via selfassembly of thiol-based monolayers on gold. Although robust for rapid prototyping, thiol monolayers suffer from limitations in terms of stability under voltage modulation and in the face of competitive ligands such as thiolated molecules naturally occurring in biofluids. Additionally, gold cannot be deployed as an NBE substrate for all biomedical applications, such as in cases where molecular measurements coupled to real-time, under-the-sensor tissue imaging is needed. Seeking to overcome these limitations, the field of NBEs is pursuing alternative ligands and electrode surfaces. In this perspective, I discuss new interface fabrication strategies that have successfully achieved NBE sensing, or that have the potential to allow NBE sensing on conductive surfaces other than gold. I hope this perspective will provide the reader with a fresh view of how future NBE interfaces could be constructed and will serve as inspiration for the pursuit of collaborative developments in the field of NBEs.

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Section: ■ Strategies Based On Self-assemblymentioning

confidence: 99%

Section: Strategies Based On Self-assemblymentioning

confidence: 99%

Beyond the Gold–Thiol Paradigm: Exploring Alternative Interfaces for Electrochemical Nucleic Acid-Based Sensing

Arroyo-Currás

2024

ACS Sens.

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“…To this end, the fluorescent and hydrophobic carboxylic acid 1-pyrenebutyric acid, 10 , was selected (Figure ). Pyrene is not only a popular fluorophore, its ability to pi-stack onto graphitic carbon surfaces means that this functional group is frequently appended to biomolecules and designer polymers in order to fabricate electrochemical sensors and devices. − Notably, the Sulfo-NHS-ester of 1-pyrenebutyric acid is not commercially available.…”

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confidence: 99%

Crossing the Solubility Rubicon: 15-Crown-5 Facilitates the Preparation of Water-Soluble Sulfo-NHS Esters in Organic Solvents

Yates,

Miles,

Spicer

et al. 2023

Bioconjugate Chem.

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The Sulfo-NHS ester is a mainstay reagent for facilitating amide bond formation between carboxylic acids and amine functionalities in water. However, the preparation of Sulfo-NHS esters currently requires hydrophobic carboxylic acids, which are poorly water-soluble, to first be reacted with the Nhydroxysulfosuccinimide sodium salt, which is insoluble in organic solvents. The mutually incompatible solvation requirements thus complicate the synthesis of Sulfo-NHS esters. As a simple, rapid, and cost-effective solution to this problem, we report that the use of 15-crown-5 to complex the sodium cation of Nhydroxysulfosuccinimide sodium salt circumnavigates these solvation incompatibility issues by rendering the N-hydroxysulfosuccinimide salt soluble in organic solvents, resulting in a cleaner esterification reaction and thus improved yields of activated ester product. We also demonstrate that the resultant "crowned" Sulfo-NHS-ester remains water-soluble and is no less reactive than its classic "uncrowned" Sulfo-NHS counterpart when used in bioconjugation reactions between protein amine-functionalities and hydrophobic carboxylic acids.

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Chemically modifying electrodes—a classical tool box

Sterin,

Tverdokhlebova,

Smutok

et al. 2024

J Solid State Electrochem

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The versatility of pyrene and its derivatives on sp2 carbon nanomaterials for bioelectrochemical applications

Cited by 10 publications

References 58 publications

Beyond the Gold–Thiol Paradigm: Exploring Alternative Interfaces for Electrochemical Nucleic Acid-Based Sensing

Beyond the Gold–Thiol Paradigm: Exploring Alternative Interfaces for Electrochemical Nucleic Acid-Based Sensing

Crossing the Solubility Rubicon: 15-Crown-5 Facilitates the Preparation of Water-Soluble Sulfo-NHS Esters in Organic Solvents

Chemically modifying electrodes—a classical tool box

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