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Direct separation of albendazole sulfoxide enantiomers by liquid chromatography on a chiral column deriving from (S)‐ N ‐(3,5‐dinitrobenzoyl)tyrosine: application to enantiomeric assays on plasma samples
Author(s) -
Lienne M.,
Caude M.,
Rosset R.,
Tambuté A.,
Delatour P.
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010208
Subject(s) - chemistry , enantiomer , chromatography , albendazole , chiral column chromatography , sulfoxide , chiral derivatizing agent , high performance liquid chromatography , organic chemistry , medicine , surgery
The direct enantiomeric resolution of albendazole sulfoxide (SOABZ), an anthelmintic drug belonging to the benzimidazole class, is reported on a chiral stationary phase (CSP) synthesized by covalent binding of (S)‐ N ‐(3,5‐dinitrobenzoyl)tyrosine‐ O ‐(2‐propen‐1‐yl) methyl ester on a γ‐mercaptopropylsilanized silica gel. A comparison with the resolution achieved on commercially available Pirkle‐type CSPs obtained from N ‐(3,5‐dinitrobenzoyl) derivatives of (R)‐phenyglycine or (S)‐phenylalanine is described. Some structurally related chiral sulfoxides including oxfendazole (SOFBZ) are also studied. Optimization of the mobile phase nature and composition is investigated showing that a hexane–dioxane–ethanol ternary mixture affords an almost baseline resolution ( R s = 1.25); however, in this case, albendazole sulfone (SO 2 ABZ) is eluted between the two sulfoxide enantiomers; accordingly, a hexane–ethanol mobile phase would be preferred for biological samples containing both metabolites. The influence of temperature on the resolution is depicted with a hexane–ethanol mobile phase. Finally, application to the enantiomeric assays of SOABZ in plasmatic extracts of rat, sheep, bovin, and man after oral administration of albendazole (sulfoxidized to SOABZ and SO 2 ABZ) is reported. Some distortions in the enantiomeric ratios are evidenced depending on the species.