Doctoral School of the Medical University of Silesia in Katowice, Faculty of Pharmaceutical Sciences in Sosnowiec, 41-200 Sosnowiec, Poland.
Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, Poland.
Molecules. 2022 Dec 25;28(1):166. doi: 10.3390/molecules28010166.
This study aimed to evaluate the lipophilicity of a series substances lowering the concentration of uric acid in blood and anti-androgen drugs by thin-layer chromatography in reversed-phase systems (RP-TLC, RP-HPTLC) and computational methods. The chromatographic parameter of lipophilicity (R) of tested compounds was determined on three stationary phases, i.e., RP18F, RP18WF and RP2F, using ethanol-water, propan-2-ol-water and acetonitrile-water in various volume compositions as mobile phases. The chromatographic analysis led to determining the experimental value of the lipophilicity parameter for each of the tested compounds, including those for which the experimental value of the partition coefficient (logP) as a measure of lipophilicity is not well described in available databases, such as febuxostat, oxypurinol, ailanthone, abiraterone and teriflunomide. The chromatographic parameters of lipophilicity were compared with the logP values obtained with various software packages, such as AClogP, AlogPs, AlogP, MlogP, XlogP2, XlogP3, ACD/logP and logP. The obtained results indicate that, among selected chromatographic parameters of lipophilicity, both experimental and calculated logP values gave similar results, and these RP-TLC or RP-HPTLC systems can be successfully applied to estimate the lipophilicity of studied heterocyclic compounds belonging to two different pharmacological groups. This work also illustrates the similarity and difference existing between the tested compounds under study using the chemometric methods, such as principal component analysis (PCA) and cluster analysis (CA). In addition, a relatively new approach based on the sum of ranking differences (SRD) was used to compare the chromatographically obtained and theoretical lipophilicity descriptors of studied compounds.
本研究旨在通过反相薄层色谱法（RP-TLC、RP-HPTLC）和计算方法评估一系列降低血液尿酸浓度的亲脂性物质和抗雄激素药物。在三种固定相（RP18F、RP18WF 和 RP2F）上，使用乙醇-水、丙-2-醇-水和乙腈-水作为流动相，以不同的体积组成，测定了测试化合物的亲脂性（R）色谱参数。色谱分析确定了每种测试化合物的亲脂性参数的实验值，包括那些在可用数据库中无法很好描述的化合物，如非布司他、氧嘌呤醇、苦木酮、阿比特龙和特立氟胺。亲脂性的色谱参数与各种软件包（如 AClogP、AlogPs、AlogP、MlogP、XlogP2、XlogP3、ACD/logP 和 logP）获得的 logP 值进行了比较。所得结果表明，在所选择的亲脂性色谱参数中，实验和计算的 logP 值均给出了相似的结果，这些 RP-TLC 或 RP-HPTLC 系统可成功用于估计属于两个不同药理组的研究杂环化合物的亲脂性。这项工作还使用化学计量学方法（如主成分分析（PCA）和聚类分析（CA））说明了研究中测试化合物之间存在的相似性和差异。此外，还使用基于排序差异总和（SRD）的相对较新方法比较了研究化合物的色谱获得和理论亲脂性描述符。
