title: Effect of the water content on the retention and enantioselectivity of albendazole and fenbendazole sulfoxides using amylose-based chiral stationary phases in organic-aqueous conditions.
abstract: Four commercially available immobilized amylose-derived CSPs (Chiralpak IA-3, Chiralpak ID-3, Chiralpak IE-3 and Chiralpak IF-3) were used in the HPLC analysis of the chiral sulfoxides albendazole (ABZ-SO) and fenbendazole (FBZ-SO) and their in vivo sulfide precursor (ABZ and FBZ) and sulfone metabolite (ABZ-SO2 and FBZ-SO2) under organic-aqueous mode. U-shape retention maps, established by varying the water content in the acetonitrile- and ethanol-water mobile phases, were indicative of two retention mechanisms operating on the same CSP. The dual retention behavior of polysaccharide-based CSPs was exploited to design greener enantioselective and chemoselective separations in a short time frame. The enantiomers of ABZ-SO and FBZ-SO were baseline resolved with water-rich mobile phases (with the main component usually being 50-65% water in acetonitrile) on the IF-3 CSP and ethanol-water 100:5 mixture on the IA-3 and IE-3 CSPs. A simultaneous separation of ABZ (or FBZ), enantiomers of the corresponding sulfoxide and sulfone was achieved on the IA-3 using ethanol-water 100:60 (acetonitrile-water 100:100 for FBZ) as a mobile phase.
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy.
authors.forename: Sabrina
authors.initials: S
authors.lastname: Materazzo
authors.affiliation: Department of Drug Chemistry and Technologies, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
authors.forename: Simone
authors.initials: S
authors.lastname: Carradori
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy.
authors.forename: Rosella
authors.initials: R
authors.lastname: Ferretti
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy.
authors.forename: Bruno
authors.initials: B
authors.lastname: Gallinella
authors.affiliation: Department of Drug Chemistry and Technologies, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
authors.forename: Daniela
authors.initials: D
authors.lastname: Secci
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy. Electronic address: rcirilli@iss.it.
authors.forename: Roberto
authors.initials: R
authors.lastname: Cirilli
mesh_terms: D000097:Acetonitriles; D015766:Albendazole / Q000031:analogs & derivatives* / Q000737:chemistry; D000688:Amylose / Q000737:chemistry; D001562:Benzimidazoles; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D000431:Ethanol; D005273:Fenbendazole / Q000031:analogs & derivatives* / Q000737:chemistry; D000432:Methanol; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry; D013454:Sulfoxides / Q000737:chemistry*; D014867:Water
chemical_list: D000097:Acetonitriles; D001562:Benzimidazoles; D013440:Sulfides; D013450:Sulfones; D013454:Sulfoxides; D014867:Water; D000431:Ethanol; D005273:Fenbendazole; D000688:Amylose; D015766:Albendazole; C027186:albendazole sulfoxide; C011030:oxfendazole; D000432:Methanol; C032159:acetonitrile
keywords: Albendazole; Chiral sulfoxides; Enantiomer separation; Fenbendazole; Organic–aqueous mobile phase; Polysaccharide chiral stationary phase