Self-assembly of pyridine-modified lipoic acid derivatives on gold and their interaction with thyroxine (T4)

Willem Martin Albers (Corresponding Author), Roberto Milani (Corresponding Author), Kirsi Tappura, Tony Munter, G. Resnati, Pierangelo Metrangolo

Research output: Contribution to journalArticleScientificpeer-review

1 Citation (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)3500-3513
Number of pages14
JournalInternational Journal of Molecular Sciences
Volume14
Issue number2
DOIs
Publication statusPublished - 2013
MoE publication typeA1 Journal article-refereed

Fingerprint

lipoic acid
thyroxine
Thioctic Acid
Thyroxine
Gold
Pyridine
Self assembly
self assembly
pyridines
Ligands
gold
Derivatives
Acids
ligands
Buffers
Surface Plasmon Resonance
Surface plasmon resonance
buffers
interactions
surface plasmon resonance

Keywords

  • thyroxine
  • self-assembly
  • imprinting
  • noncovalent interactions
  • Surface Plasmon Resonance (SPR)

Cite this

Albers, Willem Martin ; Milani, Roberto ; Tappura, Kirsi ; Munter, Tony ; Resnati, G. ; Metrangolo, Pierangelo. / Self-assembly of pyridine-modified lipoic acid derivatives on gold and their interaction with thyroxine (T4). In: International Journal of Molecular Sciences. 2013 ; Vol. 14, No. 2. pp. 3500-3513.
@article{39d71e95a1e24a488ce66338d63bb61e,
title = "Self-assembly of pyridine-modified lipoic acid derivatives on gold and their interaction with thyroxine (T4)",
abstract = "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.",
keywords = "thyroxine, self-assembly, imprinting, noncovalent interactions, Surface Plasmon Resonance (SPR)",
author = "Albers, {Willem Martin} and Roberto Milani and Kirsi Tappura and Tony Munter and G. Resnati and Pierangelo Metrangolo",
note = "Project code: 70722 Halosense Project code: 75656 Project code: 77282",
year = "2013",
doi = "10.3390/ijms14023500",
language = "English",
volume = "14",
pages = "3500--3513",
journal = "International Journal of Molecular Sciences",
issn = "1661-6596",
publisher = "MDPI",
number = "2",

}

Self-assembly of pyridine-modified lipoic acid derivatives on gold and their interaction with thyroxine (T4). / Albers, Willem Martin (Corresponding Author); Milani, Roberto (Corresponding Author); Tappura, Kirsi; Munter, Tony; Resnati, G.; Metrangolo, Pierangelo.

In: International Journal of Molecular Sciences, Vol. 14, No. 2, 2013, p. 3500-3513.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Self-assembly of pyridine-modified lipoic acid derivatives on gold and their interaction with thyroxine (T4)

AU - Albers, Willem Martin

AU - Milani, Roberto

AU - Tappura, Kirsi

AU - Munter, Tony

AU - Resnati, G.

AU - Metrangolo, Pierangelo

N1 - Project code: 70722 Halosense Project code: 75656 Project code: 77282

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - thyroxine

KW - self-assembly

KW - imprinting

KW - noncovalent interactions

KW - Surface Plasmon Resonance (SPR)

U2 - 10.3390/ijms14023500

DO - 10.3390/ijms14023500

M3 - Article

VL - 14

SP - 3500

EP - 3513

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

SN - 1661-6596

IS - 2

ER -