Thiolated Chiral Naphthalene Diimide Derivatives as Effective Selectors of the β‐Blocker Atenolol Enantiomers

Abstract

Atenolol β‐blocker drug (ATN) to treat hypertension and cardiovascular disorders such as angina pectoris is manufactured commercially in a racemic form, while only its (S)‐enantiomer shows selective β1‐blocking activity. Here, a new axially chiral thiolated naphthalene diimide derivatives (HS‐BIN‐NDI) for the rapid, simple, and sensitive detection of ATN enantiomers is presented. The Surface Plasmon Resonance (SPR) and Atomic Force Microscopy (AFM) experiments show that interactions between a chiral selector and a chiral analyte occur only when their configurations are opposite. The extensive computational simulations support this finding. The association coefficient determined by SPR is high (105‐106 M−1 s−1) and indicates that the interactions are electrostatic. The analytical utility of atropisomeric HS‐BIN‐NDIs is proven, and the voltammetric sensors designed to determine ATN enantiomers are constructed. The developed sensors are characterized by a wide analytical operating range from 5.0·10−3 to 1.0 µm, nanomolar detection limit, high selectivity, and a long lifetime. Several additives like urea, creatinine, glucose, human albumin, and hemoglobin do not affect ATN sensing.