Rational Design of a Redox-Labeled Chiral Target for an Enantioselective Aptamer-Based Electrochemical Binding Assay

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 mol. 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-L-Tym aptamer was demonstrated. The access to both enantiomeric tracer mols. 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.

Références

Titre
Rational Design of a Redox-Labeled Chiral Target for an Enantioselective Aptamer-Based Electrochemical Binding Assay
Type de publication
Article de revue
Année de publication
2014
Revue
Chemistry - A European Journal
Volume
20
Pagination
2953–2959
ISSN
1521-3765
Soumis le 8 septembre 2022