Electroanalytical exploitation of quinone–thiol interactions: application to the selective determination of cysteine

Hignett, Geraldine; Threlfell, Sarah; Wain, Andrew J.; Lawrence, Nathan S.; Wilkins, Shelley J.; Davis, James A.; Compton, Richard G.; Cardosi, Marco F.

doi:10.1039/b008616i

Cited by 70 publications

(43 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Square wave voltammetric techniques allowed electrochemical processes due to the unreacted orthoquinone and the accumulated adduct species to be resolved such that the latter could be effected as a means of quantifying cysteine [95]. A second reaction process relying upon the reaction of various quinone structures with cysteine has also been detailed [26]. It was found that through analysing the electrochemical reduction sweep that the quinone and the quinone-cysteine reduction peaks were spatially resolved.…”

Section: Derivatization Detectionmentioning

confidence: 99%

Electrochemical Determination of Thiols: A Perspective

et al. 2002

Self Cite

View full text Add to dashboard Cite

Monitoring thiol concentrations within physiological fluids has risen to considerable importance within the biomedical communities as our appreciation of the various roles that these compounds can perform has increased. Their utilization as biomarkers for numerous clinical conditions has prompted considerable interest in the development of analytical protocols that enable speedy measurements to be made. As such, a large number of procedures have arisen. This perspective highlights the contexts where physiological thiol measurements are required and describes the basis of many of the current electrochemical approaches to their determination. The collation of information from a broad range of sources covering the major electrochemical approaches (direct, indirect, and post column/capillary detection) has been achieved and the salient points of each technique critically appraised. The various characteristics and limitations of the systems are compared and contrasted with the analytical parameters (matrix, methodology, detection limit etc) from each major grouping tabulated to aid direct comparison.

show abstract

Section: Derivatization Detectionmentioning

confidence: 99%

Electrochemical Determination of Thiols: A Perspective

et al. 2002

Self Cite

View full text Add to dashboard Cite

show abstract

“…23 Therefore, many researches have been focused on the determination of cysteine in pharmaceuticals, urine, serum, and plasma. [24][25][26][27][28][29] Although HPLC 26 and electrochemical analyses 27 are versatile for determining cysteine, they require expensive equipment. Spectrophotometry 28,29 and flourometry, 30 which are rather ubiquitous techniques, are alternatives, but their poor selectivity and laborious procedures have limited their application.…”

Section: Introductionmentioning

confidence: 99%

Simple and Selective Sensing of Cysteine Using Gold Nanoparticles Conjugated with a Thermoresponsive Copolymer Having Carboxyl Groups

et al. 2007

View full text Add to dashboard Cite

We describe a simple, yet selective cysteine sensor based on gold nanoparticles (AuNPs) conjugated with thermoresponsive copolymers, the carboxyl groups of which are incorporated. Copolymer-conjugated AuNPs, used as the cysteine sensor, in a solution form sediment when cysteine is added. Heating followed by cooling the solution induces phase transitions of the thermoresponsive copolymers, resulting in an acceleration of sedimentation of the copolymer-conjugated AuNPs. The absorbance of supernatants at 520 nm, which are ascribed to a surface plasmon band of discrete AuNPs, decays with increasing concentration of cysteine. Sedimentation of the copolymer-conjugated AuNPs is specific to cysteine. The addition of other popular amino acids, or ascorbic acid, causes no sedimentation of the AuNPs. The relationship between the absorbance of the supernatant at 520 nm and the cysteine concentration provides a sigmoidal profile at a concentration range between 1 × 10 -6 to 6 × 10 -6 mol dm -3 . The determination of cysteine in a supplement is achieved using an inflection point on the sigmoidal profiles.

show abstract

“…As 89.3% of human proteins and 17% of their tryptic peptides possess at least one cysteine [59], the proposed methodology was targeted toward cysteine mass tagging. Based on recent works on the electrochemical detection of sulfides [60,61], thiols [62], and cysteine [63,64] with quinone derivatives, we focused on the potential use of electrogenerated benzoquinones (coming from the oxidation of hydroquinones) able to react specifically with cysteine residues during electrospray mass spectrometric measurements. We present below a review of the different steps of the development of on-line electrochemical probes for cysteine mass tagging, from the proof of principle [65] to the elucidation of the tagging reaction mechanism [66], characterization of the microspray design influence on the tagging process [67], search for an optimal electrochemical probe [68], and final application to protein identification [69].…”

mentioning

confidence: 99%

Generation of mass tags by the inherent electrochemistry of electrospray for protein mass spectrometry

Roussel

Dayon

Lion

et al. 2004

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

We present herein a review of our work on the on-line electrochemical generation of mass tags toward cysteine residues in peptides and proteins. Taking advantage of the inherent electrochemical nature of electrospray generated from a microfabricated microspray emitter, selective probes for cysteine were developed and tested for on-line nonquantitative mass tagging of peptides and proteins. The nonquantitative aspect of the covalent tagging thus allows direct counting of free cysteines in the mass spectrum of a biomolecule through additional adduct peaks. Several substituted hydroquinones were investigated in terms of electrochemical properties, and their usefulness for on-line mass tagging during microspray experiments were assessed with L-cysteine, peptides, and intact proteins. Complementarily, numerical simulations were performed to properly understand the respective roles of mass transport, kinetics of electrochemical-chemical reactions, and design of the microspray emitter in the mass tagging overall efficiency. Finally, the on-line electrochemical tagging of cysteine residues was applied to the analysis of tryptic peptides of purified model proteins for protein identification through peptide mass fingerprinting. (J Am Soc Mass Spectrom 2004, 15, 1767-1779

show abstract

Electroanalytical exploitation of quinone–thiol interactions: application to the selective determination of cysteine

Cited by 70 publications

References 44 publications

Electrochemical Determination of Thiols: A Perspective

Electrochemical Determination of Thiols: A Perspective

Simple and Selective Sensing of Cysteine Using Gold Nanoparticles Conjugated with a Thermoresponsive Copolymer Having Carboxyl Groups

Generation of mass tags by the inherent electrochemistry of electrospray for protein mass spectrometry

Contact Info

Product

Resources

About