Abstract The retention behavior, lipophilicity of 16,17-secoestrone derivatives and efficiency in the separation of halogenated derivatives by HPLC with pentafluorophenyl-propyl stationary phase (F5) were studied. Methanol-water (MeOH-W) and acetonitrile-water (ACN-W) were used as mobile phases in proportions according to nomograph of iso-eluotropic binary solvent mixtures. Since mobile phase ACN-W was more effective eluent, the retention behavior of 16,17-secoesterone derivatives has further been evaluated, with water content increasing in increments of 5%. The retention constants log k for mobile phases MeOH-W and ACN-W, have been compared by applying Student’s paired t-test and Fisher’s F-test to determine the applicability of the nomograph to this column. Linear correlations were obtained between parameters log k0 and log P, as well as φ0 and log P, for both MeOH-W and ACN-W eluents. Compared with log k0, the hydrophobicity index φ0 proved to be better parameter for lipophylicity estimation of these compounds. According to the separation efficacy of individual components, as well as mixtures of halogenated secoestone compounds, chromatographic columns can be placed in the following order: C18> F5> C8. This result is of huge importance for the field of synthesis, purification and characterization of novel biologically and pharmacologically active compounds and steroids among them. Graphical Abstract

中文翻译：

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HPLC 亲脂性测定和分离具有生物活性的 16,17-secoesterone 衍生物的新挑战——使用五氟苯基-丙基色谱柱

摘要 研究了16,17-癸烯雌酮衍生物的保留行为、亲脂性和使用五氟苯基-丙基固定相(F5) HPLC 分离卤代衍生物的效率。甲醇-水 (MeOH-W) 和乙腈-水 (ACN-W) 用作流动相，其比例根据各向异性二元溶剂混合物的列线图。由于流动相 ACN-W 是更有效的洗脱液，因此进一步评估了 16,17-secoesterone 衍生物的保留行为，其中水含量以 5% 的增量增加。流动相 MeOH-W 和 ACN-W 的保留常数 log k 已通过应用 Student 配对 t 检验和 Fisher F 检验进行比较，以确定列线图对该色谱柱的适用性。在参数 log k0 和 log P 之间获得线性相关性，以及 φ0 和 log P，适用于 MeOH-W 和 ACN-W 洗脱液。与 log k0 相比，疏水性指数 φ0 被证明是这些化合物亲脂性评估的更好参数。根据单个组分的分离效果，以及卤代辅石化合物的混合物，色谱柱可按以下顺序排列：C18>F5>C8。这一结果对于合成、纯化和表征新的具有生物和药理活性的化合物和类固醇的领域具有重要意义。图形概要 以及卤化secoestone化合物的混合物，色谱柱可以按以下顺序放置：C18> F5> C8。这一结果对于合成、纯化和表征新的具有生物和药理活性的化合物和类固醇的领域具有重要意义。图形概要 以及卤化secoestone化合物的混合物，色谱柱可以按以下顺序放置：C18> F5> C8。这一结果对于合成、纯化和表征新的具有生物和药理活性的化合物和类固醇的领域具有重要意义。图形概要