Use of Selected Topological Indexes for Evaluation of Lipophilicity of Steroid Compounds Investigated by RP-HPTLC

Abstract

The selected steroid compounds (androsterone, epi-androsterone, dehydroepi-androsterone, testosterone, stigmasterol, β-sitosterol, estradiol, hydrocortisone, and cholesterol) were investigated with the use reversed phase high performance thin layer chromatography on RP18W plates (#1.14296, E. Merck), using methanol–water, acetonitrile–water in different volume compositions as a mobile phases. The chromatographic parameters of lipophilicity (RMW) of the studied steroids were determined. Topological indexes based on the adjacency matrix: Gutman (M, Mν), Randic (oχν, 1χν, oχν, and 1χν), based on distance matrix: Rouvray (R), Wiener (W), and Pyka (A, oB, and 1B), and also based on information theory (ISA and ĪSA) and theoretical partition coefficients (Alog Ps, IAlog P, Clog P, log PKowwin, xlog P, and miLog P) for investigated steroids were calculated. It was found that lipophilicity determined chromatographically (RMW) correlated best with topological indices oχν, 1χν, R, W, A, and 1B. However, theoretical partition coefficient values (Alog Ps, IAlog P, Clog P, log PKowwin, xlog P, and miLog P) correlated best with topological index ĪSA.