Electrochemical Properties of Glutathione Monolayer on Mercury Surface

Fang, Cheng; Zhou, Xingyao

doi:10.1002/1521-4109(200205)14:10<711::aid-elan711>3.0.co;2-7

Cited by 9 publications

(5 citation statements)

References 14 publications

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“…The molecule has a multitude of physiological functions, such as redox-buffering, detoxification, and antioxidant activity. Furthermore, GSH is cheap, which makes it an attractive candidate for surface and electrode modification − and the synthesis of monolayer-protected nanoparticles. − Glutathione-modified gold surfaces were for example used for specific protein binding. , Copper(II) and lanthanide(III) ions were found to bind strongly to glutathione-modified gold electrodes. ,, The affinity for the ions was assigned to the carboxylic acid groups and depended on pH . On the basis of voltammetry and electrochemical quartz crystal microbalance (EQCM) investigations, it was furthermore proposed that during the redox process of Cu 2+ /Cu + the glutathione monolayer could rearrange …”

Section: Introductionmentioning

confidence: 99%

“…The molecule has a multitude of physiological functions, 9 such as redoxbuffering, detoxification, and antioxidant activity. Furthermore, GSH is cheap, which makes it an attractive candidate for surface and electrode modification [10][11][12][13][14][15][16][17][18][19][20][21][22][23] and the synthesis of monolayer-protected nanoparticles. [24][25][26] Glutathione-modified gold surfaces were for example used for specific protein binding.…”

Section: Introductionmentioning

confidence: 99%

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l-Glutathione Chemisorption on Gold and Acid/Base Induced Structural Changes: A PM-IRRAS and Time-Resolved in Situ ATR-IR Spectroscopic Study

2005

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Adsorption of the tripeptide L-glutathione (γ-glu-cys-gly) on gold surfaces was investigated by polarization modulation infrared reflection absorption spectroscopy (PM-IRRAS) and attenuated total reflection (ATR) infrared spectroscopy. PM-IRRAS was used to study ex situ the adsorbate layer prepared from aqueous solutions at different pH, whereas ATR-IR was applied to study in situ adsorption from ethanol in the presence and absence of acid and base. ATR-IR was furthermore combined with modulation spectroscopy in order to investigate the reversible changes within the adsorbate layer induced by acid and base stimuli, respectively. The molecule is firmly anchored on the gold surface via the thiol group of the cys part. However, the ATR-IR spectra in ethanol indicate a further interaction with the gold surface via the carboxylic acid group of the gly part of the molecule, which deprotonates upon adsorption. Hydrochloric acid readily protonates the two acid groups of the adsorbed molecule. During subsequent ethanol flow the acid groups deprotonate again, a process which proceeds in two distinct steps: a fast step associated with the deprotonation of the acid in the glu part of the molecule and a considerably slower step associated with deprotonation of the acid in the gly moiety. The latter process is assisted by the interaction of the corresponding acid group with the surface. The spectra furthermore indicate a rearrangement of the hydrogen bonding network within the adsorbate layer upon deprotonation. Depending on the protonation state during adsorption of Lglutathione, the response toward identical protonation-deprotonation stimuli is significantly different. This is explained by the ionic state-dependent shape of the molecule, as supported by density functional theory calculations. The different shapes of the individual molecules during layer formation thus influence the structure of the adsorbate layer.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

l-Glutathione Chemisorption on Gold and Acid/Base Induced Structural Changes: A PM-IRRAS and Time-Resolved in Situ ATR-IR Spectroscopic Study

2005

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“…The molecule has a multitude of physiological functions, 72 such as redox buffering, detoxification, and antioxidant activity. Furthermore, GSH is cheap, which makes it an attractive candidate for surface and electrode modification [73][74][75][76][77][78][79][80][81][82][83][84][85][86] and the synthesis of monolayer protected nanoparticles. 54,87,88 GSH SAMs undergo reversible conformational changes induced by acid and base stimuli.…”

Section: Attenuated Total Reflection Infrared Spectroscopymentioning

confidence: 99%

Probing chiral interfaces by infrared spectroscopic methods

Bieri

Gautier

Bürgi

2007

Phys. Chem. Chem. Phys.

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Biological homochirality on earth and its tremendous consequences for pharmaceutical science and technology has led to an ever increasing interest in the selective production, the resolution and the detection of enantiomers of a chiral compound. Chiral surfaces and interfaces that can distinguish between enantiomers play a key role in this respect as enantioselective catalysts as well as for separation purposes. Despite the impressive progress in these areas in the last decade, molecular-level understanding of the interactions that are at the origin of enantiodiscrimination are lagging behind due to the lack of powerful experimental techniques to spot these interactions selectively with high sensitivity. In this article, techniques based on infrared spectroscopy are highlighted that are able to selectively target the chiral properties of interfaces. In particular, these methods are the combination of Attenuated Total Reflection InfraRed (ATR-IR) with Modulation Excitation Spectroscopy (MES) to probe enantiodiscriminating interactions at chiral solid-liquid interfaces and Vibrational Circular Dichroism (VCD), which is used to probe the structure of chirally-modified metal nanoparticles. The former technique aims at suppressing signals arising from non-selective interactions, which may completely hide the signals of interest due to enantiodiscriminating interactions. Recently, this method was successfully applied to investigate enantiodiscrimination at self-assembled monolayers of chiral thiols on gold surfaces. The nanometer size analogues of the latter--gold nanoparticles protected by a monolayer of a chiral thiol--are amenable to VCD spectroscopy. It is shown that this technique yields detailed structural information on the adsorption mode and the conformation of the adsorbed thiol. This may also turn out to be useful to clarify how chirality can be bestowed onto the metal core itself and the nature of the chirality of the latter, which is manifested in the metal-based circular dichroism activity of these nanoparticles.

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“…Thanks to its SH group, GSH has been studied by polarographic methods [54][55][56][57]. Nowadays, it is possible to observe the marked increase of interest in an electrochemical study of thiol compounds including glutathione [39,58,59], first of all, due to the suggestion and development of new sensors, biosensors and biochips [36,[60][61][62][63][64][65][66][67]. One of the interesting ability of glutathione is to bind number of biologically active molecules including heavy metals via SH groups [68][69][70].…”

Section: Cyclic Voltammograms Of Gsh Gssg and Gsnomentioning

confidence: 99%

“…Recently, we have observed the electrochemical behaviour of glutathione (GSH and GSSG) on the hanging mercury drop electrode in the presence of borate buffer and have studied the influence of tris(2-carboxyethyl)phosphine (TCEP) as a reducing agent by cyclic voltammetry [50]. This method does not require any derivatization reagent and even oxidized glutathione may be detected simultaneously [50,64]. Here we applied this technique for the analysis of GSH, GSSG and GSNO.…”

Section: Cyclic Voltammograms Of Gsh Gssg and Gsnomentioning

confidence: 99%