title: Rational design of a redox-labeled chiral target for an enantioselective aptamer-based electrochemical binding assay.
abstract: A series of redox-labeled L-tyrosinamide (L-Tym) derivatives was prepared and the nature of the functional group and the chain length of the spacer were systematically varied in a step-by-step affinity optimization process of the tracer for the L-Tym aptamer. The choice of the labeling position on L-Tym proved to be crucial for the molecular recognition event, which could be monitored by cyclic voltammetry and is based on the different diffusion rates of free and bound targets in solution. From this screening approach an efficient electroactive tracer emerged. Comparable dissociation constants Kd were obtained for the unlabeled and labeled targets in direct or competitive binding assays. The enantiomeric tracer was prepared and its enantioselective recognition by the corresponding anti-D-Tym aptamer was demonstrated. The access to both enantiomeric tracer molecules opens the door for the development of one-pot determination of the enantiomeric excess when using different labels with well-separated redox potentials for each enantiomer.
authors: ITODYS, UMR 7086 CNRS, Université Paris Diderot, Sorbonne Paris Cité, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France).
authors: Julie
authors: J
authors: Moreau
authors: Lylian
authors: L
authors: Challier
authors: Noémie
authors: N
authors: Lalaoui
authors: François
authors: F
authors: Mavré
authors: Vincent
authors: V
authors: Noël
authors: Benoît
authors: B
authors: Limoges
authors: Bernd
authors: B
authors: Schöllhorn
authors: Claire
authors: C
authors: Fave
mesh_terms: D052157:Aptamers, Nucleotide / Q000737:chemistry*; D001667:Binding, Competitive; D004058:Diffusion; D004563:Electrochemistry; D019075:Electrophoresis, Capillary; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D052157:Aptamers, Nucleotide; D009841:Oligonucleotides; C036387:tyrosinamide; D014443:Tyrosine
keywords: aptamers; chirality; electrochemistry; enantioselectivity; redox labeling