Chiral nanocomposite of sulfobutyl ether-β-cyclodextrin embedded in carbon nanofibers for enantioselective electrochemical discrimination of amlodipine, metoprolol and clenbuterol enantiomers

Abstract

A highly sensitive and selective electrochemical chiral sensor was developed based on the competitive supramolecular interaction of carbon nanofibers (CNFs) embedded sulfobutyl ether-β-cyclodextrin (SBE-β-CD) with optically active cationic drugs at glassy carbon electrode (GCE). The difference in intermolecular hydrogen bonding/stability constant/enantioselectivity coefficient and Gibbs free energy of anionic host SBE-β-CD with enantiomers of amlodipine (R-/S-AML), clenbuterol (R-/S-CBL) and metoprolol (R-/S-MET) as a guest paved the way for efficient discrimination. The proposed sensing platform (CNFs-SBE-β-CD/GCE) could recognize the aforementioned enantiomers based on the discernible difference of peak potential (S/R-AML (ΔEp = 135 mV), R/S-MET (ΔEp = 99 mV) and R/S-CBL (ΔEp = 111 mV). The binding mechanisms and thermodynamic study of the enantiospecific behavior have been investigated using the host-guest chemistry approach inside the nanocavity and results suggest that S-AML, R-MET, and R-CBL show stronger stability constants than their antipodes. Formation of the diastereomeric complex was taken as a measure of enantioselectivity and experimental results indicated that anionic SBE-β-CD is a better chiral ligand than neutral cyclodextrins. The fabricated sensor could be a useful low-cost electrochemical tool for molecular recognition of a variety of cationic species not only of drugs but also from other sources.