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Among the various methods exploitable to determine 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 cholesterol 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 (1)H-(13)C, (1)H-(31)P, and (1)H-(29)Si cross-polarization magic-angle-spinning nuclear magnetic resonance (CP MAS NMR) spectroscopy. Its chromatographic behavior has been studied by classical classification tests for RPLC columns. Despite its low surface coverage, the material produced exhibits high shape selectivity, possibly due to the organization of the grafted moieties.

The properties of four cholesteric bonded stationary phases differing in the nature of the spacer and the end-capping were assessed using simple chromatographic tests based on the retention of nonpolar compounds and of planar or nonplanar probe solutes. All cholesteric columns showed a hydrophobicity close to that of conventional octadecyldimethylsilyl (ODS) materials. Non-end-capped cholesteric bonded phases showed greater selectivity than ODS ones and both end-capped cholesteric bonded phases exhibit behavior intermediate between that of the non-end-capped original material and that of the ODS bonded phase.