A Cyclodextrin Self-Assembled Monolayer (SAM) Based Surface Plasmon Resonance (SPR) Sensor for Enantioselective Analysis of Thyroxine

Shahgaldian, Patrick; Hegner, Martin; Pieles, Uwe

doi:10.1007/s10847-005-0248-3

Cited by 21 publications

(15 citation statements)

References 23 publications

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“…To our opinion, the most elegant application of these systems is their use for building nanoscale molecular printboards [62]. We used these self-assembled monolayers (SAMs) to build a SPR-based sensor, able to discriminate between enantiomers of thyroxine[56]. In Figure 4 are presented binding sensograms obtained for d - and l -enantiomers of thyroxine, molecular formula and apparent affinity constants for varying proportions of each enantiomer.…”

Section: Cyclodextrins For Chiral Sensingmentioning

confidence: 99%

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Shahgaldian

Pieles

2006

Sensors

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123

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Abstract:In view of the chiral nature of many bio-molecules (and all bio-macromolecules), most of therapeutically active compounds which target these molecules need to be chiral and "good handed" to be effective. In addition to asymmetric synthetic and separation methodologies, enantioselective chemical sensors, able to distinguish between two enantiomers of the same molecule, are of relevance. In order to design these sensing tools, two major classes of enantioselective layers have been developed. The first is based on molecularly imprinted polymers which are produced (polymerized) in the presence of their target, thus the polymeric material keep in "memory" the size and the shape of this molecule and the system could be used for sensing (not reviewed here). The second approach makes use of sensitive layers containing chiral macrocyclic receptors able of stereoselective molecular recognition; these receptors are mainly based on cyclodextrins. In this contribution, are reviewed achievements in the use of native or chemically modified cyclodextrins for chiral sensing purposes (at interfaces). Potentialities of other chiral macrocycles based on calixarenes, calix-resorcinarenes or crown-ethers as supramolecular receptors for enantioselective sensing are discussed.

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Section: Cyclodextrins For Chiral Sensingmentioning

confidence: 99%

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Shahgaldian

Pieles

2006

Sensors

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123

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“…Similar affinity results were reported by SPR measurement as well. 36 Such higher affinity difference is likely due to the deep inclusion of the hydrophobic part of thyroxine in the lipophilic cavity of the cyclodextrin skeleton such that the chiral center and the polar functions of thyroxine are segregated outside the macro cycle. 35 …”

Section: Resultsmentioning

confidence: 99%

Regenerative Electronic Biosensors Using Supramolecular Approaches

et al. 2013

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A supramolecular interface for Si nanowire FETs has been developed with the aim of creating regenerative electronic biosensors. The key to the approach are Si-NWs functionalized with β-Cyclodextrin (β-CD), to which receptor moieties can be attached with an orthogonal supramolecular linker. Here we demonstrate full recycling using the strongest biomolecular system known, streptavidin (SAv)-biotin. The bound SAv and the linkers can be selectively removed from the surface through competitive desorption with concentrated β-CD, regenerating the sensor for repeated use. An added advantage of β-CD is the possibility of stereoselective sensors, and we demonstrate here the ability to quantify the enantiomeric composition of chiral targets.

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“…With Surface Plasmon Resonance (SPR), the binding of T4 and its tri-iodinated analogue T3 can be studied in real time without the need for labeling [15]. …”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Pyridine-Modified Lipoic Acid Derivatives on Gold and Their Interaction with Thyroxine (T4)

Albers

Milani

Tappura

et al. 2013

IJMS

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Pyridyl derivatives of lipoic acid were prepared as ligands for the study of the interaction with thyroxine (T4). Thin self-assembled films of the ligands were prepared in 70% ethanol on gold and their interaction with T4 was studied by titration experiments in an aqueous buffer solution using Surface Plasmon Resonance (SPR). The thickness and refractive index of the ligand layers were calculated from SPR spectra recorded in two media, also allowing for surface coverage and the density of the layers to be estimated. Two ligands, a 4-pyridyl and a bis(2-hydroxyethyl) derivative of lipoic acid, were selected to investigate the feasibility for producing molecularly imprinted self-assembled layers on gold for T4. The methodology was to co-assemble T4 and the ligand onto the gold surface, elute the T4 from the layer under alkaline conditions, and study the rebinding of T4 to the layer. Multiple elution/rebinding cycles were conducted in different buffer solutions, and rebinding of T4 could be observed, with a moderate binding affinity that depended greatly on the solvent used. More optimal binding was observed in HBS buffer, and the affinity of the interaction could be slightly increased when the 4-pyridyl and bis(2-hydroxy-ethyl) derivatives of lipoic acid were combined in the imprinted layer.

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A Cyclodextrin Self-Assembled Monolayer (SAM) Based Surface Plasmon Resonance (SPR) Sensor for Enantioselective Analysis of Thyroxine

Cited by 21 publications

References 23 publications

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing

Regenerative Electronic Biosensors Using Supramolecular Approaches

Self-Assembly of Pyridine-Modified Lipoic Acid Derivatives on Gold and Their Interaction with Thyroxine (T4)

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