title: Application of 3 μm particle-based amylose-derived chiral stationary phases for the enantioseparation of potential histone deacetylase inhibitors.
abstract: 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.
authors: Istituto Superiore di Sanità, Dipartimento del Farmaco, Rome, Italy.
authors: Rosella
authors: R
authors: Ferretti
authors: Antonello
authors: A
authors: Mai
authors: Bruno
authors: B
authors: Gallinella
authors: Leo
authors: L
authors: Zanitti
authors: Sergio
authors: S
authors: Valente
authors: Roberto
authors: R
authors: Cirilli
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D000813:Anilides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D002934:Cinnamates / Q000737:chemistry; D002942:Circular Dichroism; D056572:Histone Deacetylase Inhibitors / Q000737:chemistry / Q000302:isolation & purification*; D007700:Kinetics; D008863:Microspheres; D010316:Particle Size; D048448:Phenylcarbamates / Q000737:chemistry*; D016062:Porosity; D011487:Protein Conformation; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000438:Alcohols; D000813:Anilides; D002934:Cinnamates; D056572:Histone Deacetylase Inhibitors; D048448:Phenylcarbamates; C080033:Chiralpak AD; D000688:Amylose