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Application of 3μm particle-based amylose-derived chiral stationary phases for the enantioseparation of potential histone deacetylase inhibitors

2011; Elsevier BV; Volume: 1218; Issue: 46 Linguagem: Inglês

10.1016/j.chroma.2011.09.052

1873-3778

Rosella Ferretti, Antonello Mai, Bruno Gallinella, Leo Zanitti, Sérgio Valente, Roberto Cirilli,

Molecular spectroscopy and chirality

In this work, we report on the difference in performance of the two 3 μm particle-based Chiralpak IA-3 and Chiralpak AD-3 chiral stationary phases (CSPs) in the direct resolution of four racemic cinnamyl 2-aminoanilides, endowed with histone deacetylase inhibitory activity. The 3 μm CSPs were explored to determine if they could provide an effective resolution of enantiomers in presence of alcoholic eluents such as pure methanol, ethanol and 2-propanol. Temperature variable enantioselective HPLC and subsequent van't Hoff analysis were performed. In most of cases the van't Hoff plots were found to show a non-linear behaviour. The knowledge of the enantiomeric elution order associated with the data coming from enantioselective HPLC permitted to advance some hypothesis about the groups involved in chiral recognition mechanism.