Separação Enantiosseletiva Da Oxibutinina: Uma Investigação Teórica E Experimental

Abstract

ENANTIOSELECTIVE SEPARATION OF OXYBUTYNIN: A THEORETICAL AND EXPERIMENTAL INVESTIGATION. In this work, we have studied both experimentally and theoretically the oxybutynin chiral discrimination. According to the main results, the enantioseparation of oxybutynin was efficiently achieved by high performance liquid chromatography in normal phase using the Chiralpak® AD column, which has amylose tris (3,5‐dimethylphenylcarbamate) as a chiral selector. The energetic and structural parameters obtained via density functional theory calculations pointed out the chiral discrimination as well as the enantiomeric elution order of oxybutynin, thus explaining, at molecular level, the experimental data. Finally, the strength of the hydrogen bonds played a key role in the discrimination between the oxybutynin diastereomeric complexes formed.

Repositioning Oxybutynin Hydrochloride: State of the Art in Synthesis, Mode of Action, Metabolism, and Formulations

“…Although high-performance thin-layer chromatography has been cited [33], enantiomers of oxybutynin have been generally separated by high-performance liquid chromatography. The silica-based support of the columns was covalently bonded to ovomucoid [34] or, more often, coated with polysaccharides such as amylose-tris(3,5-dimethylphenylcarbamate) [35,36] or cellulose-tris(4-methylbenzoate) [37]. Also reported and noteworthy is the use of β-cyclodextrin derivatives, essentially hydroxypropyl-β-cyclodextrin, as chiral selectors for the separation by high-performance liquid chromatography [38] as well as by electrophoresis [39], liquid-liquid reactive extraction [40], and recycling high-speed counter-current chromatography [41].…”

Theoretical study of the chiral separation process of atenolol and carvedilol β-blocker drugs

“…In this context, aiming to provide an auxiliary analysis to the chiral separation by HPLC as well as assisting to explain at the molecular level the EEO, computational studies have been reported in an attempt to comprehend the molecular properties involved in the formation of DCs, providing relevant information on the electronic structures and thermodynamics properties related to the complexation process [6][7][8][9][10][11][12][13][14][15][16]. Recently, our research group has been successfully performed theoretical studies via Density Functional Theory (DFT) calculations regarding the enantioselective separation of three distinct chiral analytes [17][18][19]. In these works, we were able to elucidate and explain at the molecular level the experimental EEO.…”