QSRR analysis of retention behavior of androstane-3-oxime derivatives in diverse RP-UHPLC systems

A series of eighteen novel androstane-3-oxime derivatives with picolyl and picolinylidene functional groups has been evaluated from different aspects of their properties. Their significant anticancer activity against various types of cancer cells has been confirmed. Also, their lipophilicity has been evaluated by applying different chromatographic systems. As a result of conducted reversed-phase ultra-high performance liquid chromatography analysis, a database of quantitatively comparable and precise chromatographic lipophilicity measures (logk parameters) of the considered androstane-3-oxime derivatives was formed. The main aim of the present study is to evaluate, rank and correlate those parameters with in silico molecular properties (descriptors) in order to better understand their behavior in various chromatographic systems, and thereby provide insight into the retention behavior of steroidal derivatives. Another aim was to develop quantitative structure-retention relationship (QSRR) models to enable predictive modeling of chromatographic behavior in different mobile and stationary phases. The ranking of the compounds was performed by the sum of ranking differences (SRD) approach, and the QSRR modeling was performed applying multiple linear regression (MLR). The resulting models demonstrated strong predictive performance, stressing the strength of linear approach and highlighting the role of lipophilicity, topology and electronic properties in retention mechanisms.