A chromatographic study on the retention behavior of the amylose tris(3‐chloro‐5‐methylphenylcarbamate) chiral stationary phase under aqueous conditions

Abstract

In this study, the retention properties of the immobilized polysaccharide-derived Chiralpak IG-3 chiral stationary phase under aqueous-organic conditions were investigated. A systematic evaluation of the retention factors of the enantiomers of the chiral sulfoxide oxfendazole, endowed with anthelmintic activity and selected as test compound, was carried out changing progressively the water content in hydro-organic eluents containing methanol, ethanol or acetonitrile. From the results obtained with acetonitrile/water mobile phases and the associated retention plots, clear U-shape retention dependencies, indicative of the interplay of both hydrophilic interaction liquid chromatography and reversed-phase modes, were highlighted. A U-turn point of retention mechanism was recorded in correspondence of the acetonitrile/water 100:40 v/v mobile phase. Retention was significantly affected by small percentages of trifluoroacetic acid or diethylamine additives incorporated in the mobile phase. It is worth emphasizing that the basic additive was more effective in reducing retention in the reversed-phase region, while the action of acid additive was more pronounced in the hydrophilic interaction liquid chromatography region. Finally, either in the transition from hydrophilic interaction liquid chromatography to reversed-phase conditions or after additive addition, the enantioselectivity did not vary significantly.

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

“…In recent developments, one (immobilized) column can operate in normal-, reverse-phase, and polar-organic modes as well as in HILIC mode and several types of columns are also available with a smaller particle size (3 µm). It provides new application possibilities [ 29 ]. Many new articles on chiral drug separation mention the use of polysaccharide-based CSPs.…”

Screening of Benzimidazole-Based Anthelmintics and Their Enantiomers as Repurposed Drug Candidates in Cancer Therapy

“…In the present study, a 250 mm × 10 mm i.d. Chiralpak IG column [33,34] was employed, in order to optimize and isolate multi-milligram quantities of enantiopure forms of ricobendazole (as also previously reported for oxfendazole). The chromatograms depicted in Figure 3 are representative of increasing amounts of ricoben-dazole (RBZ) resolved in a single chromatographic run.…”

Enantioselective HPLC analysis of escitalopram oxalate and its impurities using a cellulose‐based chiral stationary phase under normal‐ and green reversed‐phase conditions

“…The rising cost of organic solvents and the expense associated with their disposal or recycling, as well as their toxicity, has become a determining factor in inducing pharmaceutical industries to take a greener approach in developing analytical methods dedicated to establishing purity and assay of drugs [17][18][19][20][21].…”