The analysis of chromatographic behavior of homoandrostane derivatives in reversed-phase ultra-high performance liquid chromatography

Abstract

Homoandrostane derivatives, as compounds with significant bioactivity, were studied in terms of their chromatographic behavior in reversed-phase ultra-high performance liquid chromatography (RP-UHPLC). In the present study, five androstane derivatives from the series of homoandrostanes were analyzed, including: 3β-hydroxy-17-oxa-17a-homoandrost-5-en-16-one, 3β,5α-dihydroxy-17- oxa-17a-homoandrostane-6,16-dione, 17-oxa-5β,6β-epoxy-17a-homoandrostane-3,16-dione, 5α-hydroxy- 17-oxa-17a-homoandrostane-6,16-dione-3β-yl acetate and 3β-hydroxy-17-oxa-5α,6α-epoxy-Dhomoandrostan- 16-one. The compounds were analyzed by applying methanol-water mobile phases with different volume fractions of methanol, as a polar protic solvent, and logk0 parameters of each compound were determined. The outstanding correlations between in silico logP descriptors and logk0 parameters were obtained, as well as between in silico logD descriptors and logk0 parameters. The logk0 parameters are very well correlated with polar surface area (PSA) descriptor as well. The studied compounds and lipophilicity descriptors (including the chromatographic lipophilicity parameters - logk0) were clustered applying hierarchical cluster analysis (HCA) in the form of clustered heat map known as double dendrogram. Furthermore, the sum of ranking differences (SRD) method was used for the ranking of the lipophilicity measures of the analyzed homoandrostane derivatives so the most suitable lipophilicity measures of this series of compounds can be selected.

Keywords

• androstanes
• chromatography
• lipophilicity
• sum of ranking differences
• steroids