Cholesteric bonded stationary phases for high performance liquid chromatography II: synthesis, physico-chemical characterization and chromatographic behavior of a phospho-cholesteric bonded support. A new way to mimic drug/membrane interactions?
Résumé
Among the various methods exploitable to deter- mine the bioavailability of drugs, reversed-phase liquid chromatography (RPLC) appears to be suited to creation of patterns of prediction. In this context a new stationary phase was designed in this work to reproduce, in terms of chemical structure, as accurately as possible, the main elements of cellular membranes; which include phospholipids and cho- lesterol molecules. An efficient synthetic pathway was developed to prepare ligands that contain a phosphate head, a long alkyl chain chemically bonded to silica, and a cholesteric moiety, in order to mimic both hydrophilic and hydrophobic interactions, and "membrane-like" organization, respectively. The new stationary phase was characterized by Fourier- transform infra red (FTIR) and 1H-13C, 1H-31P, and 1H-29Si cross-polarization magic-angle-spinning nuclear magnetic resonance (CP MAS NMR) spectroscopy. Its chromato- graphic behavior has been studied by classical classification tests for RPLC columns. Despite its low surface coverage, thematerial produced exhibits high shape selectivity, possibly due to the organization of the grafted moieties.
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