Direct electrochemistry of horseradish peroxidase immobilized on electrografted 4-ethynylphenyl film via click chemistry

Qin, Ran; Peng, Ru; Liang, Cong; Ye, Siqiu; Xian, Yuezhong; Zhang, Wenjing; Jin, Litong

doi:10.1016/j.aca.2011.04.035

Cited by 24 publications

(21 citation statements)

References 45 publications

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“…21 The modification of proteins with azide groups was for example used to immobilize horseradish peroxidase on gold 22 or screenprinted carbon electrodes. 23 Inversely, azide was immobilized on a self-assembled monolayer and used to bind a protein previously derivatized with acetylene groups.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of Cysteine-Tagged Proteins on Electrode Surfaces by Thiol–Ene Click Chemistry

Lin

Vilà

Klein

et al. 2016

ACS Appl. Mater. Interfaces

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Thiol-ene click chemistry can be exploited for the immobilization of cysteine-tagged dehydrogenases in an active form onto carbon electrodes (glassy carbon and carbon felt). The electrode surfaces have been first modified with vinylphenyl groups by electrochemical reduction of the corresponding diazonium salts generated in situ from 4-vinylaniline. The grafting process has been optimized in order to not hinder the electrochemical regeneration of NAD(+)/NADH cofactor and soluble mediators such as ferrocenedimethanol and [Cp*Rh(bpy)Cl](+). Having demonstrated the feasibility of thiol-ene click chemistry for attaching ferrocene moieties onto those carbon surfaces, the same approach was then applied to the immobilization of d-sorbitol dehydrogenases with cysteine tag. These proteins can be effectively immobilized (as pointed out by XPS), and the cysteine tag (either 1 or 2 cysteine moieties at the N terminus of the polypeptide chain) was proven to maintain the enzymatic activity of the dehydrogenase upon grafting. The bioelectrode was applied to electroenzymatic enantioselective reduction of d-fructose to d-sorbitol, as a case study.

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Section: Introductionmentioning

confidence: 99%

Immobilization of Cysteine-Tagged Proteins on Electrode Surfaces by Thiol–Ene Click Chemistry

Lin

Vilà

Klein

et al. 2016

ACS Appl. Mater. Interfaces

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“…147 The mild conditions required for the anchoring of the entities by click chemistry make it a very convenient method for the immobilization of biological material, mainly for the development of biosensors. This way has led to the elaboration of DNA (or aptamer), 129,[161][162][163][164] enzyme, 114,141,165,166 non enzymatic protein, 167 peptide 136 or amino acid 168 -modified surfaces.…”

Section: Click Chemistrymentioning

confidence: 99%

“…starting from an azide platform) since about 2/3 of the reactions are based on the immobilization of redox groups (27 refs out of 40 against 22 refs out of 34 in the previous paragraph). The remaining 13 studies deal with the immobilization of bio-entities, [162][163][164][165][166]168 small organic molecules 158,177,178 or polymers 173 (or the initiator allowing polymerization from the surface 175,176 ).…”

Section: Click Chemistrymentioning

confidence: 99%

“…Whether they are carried out in one direction or another (azide surface and alkyne in solution, or the opposite), the couplings are made under similar operating conditions. Cupper(I) is always used as a reaction catalyst (directly added, 134,148,162,173,175 or formed in situ from cupper(II) and a reducing agent 85,105,[113][114][115]119,[121][122][123][124]127,128,132,135,139,140,142,147,149,157,158,160,[163][164][165][166]168,177,178 or electrochemically generated 137,176 ). The most common option relies on the combined use of copper(II) sulfate and ascorbic acid (or sodium ascorbate, usually in excess) as reducing agent.…”

Section: Click Chemistrymentioning

confidence: 99%

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A post-functionalization toolbox for diazonium (electro)-grafted surfaces: review of the coupling methods

2021

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“…In this context, click chemistry has been used as a versatile tool for different electrode materials functionalization using a variety of methodologies [13]. The characteristics and application of the recent configurations reported are summarized in Table 1 [10,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40]. In the following sections they are discussed according to the different functionalization strategies.…”

Section: Preparation Of Electrochemical Platformsmentioning

confidence: 99%

Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

Yáñez‐Sedeño

González‐Cortés

Campuzano

et al. 2019

Sensors

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Proper functionalization of electrode surfaces and/or nanomaterials plays a crucial role in the preparation of electrochemical (bio)sensors and their resulting performance. In this context, copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has been demonstrated to be a powerful strategy due to the high yields achieved, absence of by-products and moderate conditions required both in aqueous medium and under physiological conditions. This particular chemistry offers great potential to functionalize a wide variety of electrode surfaces, nanomaterials, metallophthalocyanines (MPcs) and polymers, thus providing electrochemical platforms with improved electrocatalytic ability and allowing the stable, reproducible and functional integration of a wide range of nanomaterials and/or different biomolecules (enzymes, antibodies, nucleic acids and peptides). Considering the rapid progress in the field, and the potential of this technology, this review paper outlines the unique features imparted by this particular reaction in the development of electrochemical sensors through the discussion of representative examples of the methods mainly reported over the last five years. Special attention has been paid to electrochemical (bio)sensors prepared using nanomaterials and applied to the determination of relevant analytes at different molecular levels. Current challenges and future directions in this field are also briefly pointed out.

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Direct electrochemistry of horseradish peroxidase immobilized on electrografted 4-ethynylphenyl film via click chemistry

Cited by 24 publications

References 45 publications

Immobilization of Cysteine-Tagged Proteins on Electrode Surfaces by Thiol–Ene Click Chemistry

Immobilization of Cysteine-Tagged Proteins on Electrode Surfaces by Thiol–Ene Click Chemistry

A post-functionalization toolbox for diazonium (electro)-grafted surfaces: review of the coupling methods

Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

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