Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds
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<sub...
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| Format: | Article |
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/1/166 |
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| author | Dawid Wardecki Małgorzata Dołowy Katarzyna Bober-Majnusz Josef Jampilek |
| author_facet | Dawid Wardecki Małgorzata Dołowy Katarzyna Bober-Majnusz Josef Jampilek |
| author_sort | Dawid Wardecki |
| collection | DOAJ |
| description | 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<sub>MW</sub>) of tested compounds was determined on three stationary phases, i.e., RP18F<sub>254</sub>, RP18WF<sub>254</sub> and RP2F<sub>254</sub>, 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<sub>exp</sub>) 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<sub>KOWWIN</sub>. 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. |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T03:29:49Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-af1176be71214d0191ad58999d519f192023-12-03T14:57:01ZengMDPI AGMolecules1420-30492022-12-0128116610.3390/molecules28010166Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering CompoundsDawid Wardecki0Małgorzata Dołowy1Katarzyna Bober-Majnusz2Josef Jampilek3Doctoral School of the Medical University of Silesia in Katowice, Faculty of Pharmaceutical Sciences in Sosnowiec, 41-200 Sosnowiec, PolandDepartment of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, PolandDepartment of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, PolandDepartment of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 842 15 Bratislava, SlovakiaThis 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<sub>MW</sub>) of tested compounds was determined on three stationary phases, i.e., RP18F<sub>254</sub>, RP18WF<sub>254</sub> and RP2F<sub>254</sub>, 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<sub>exp</sub>) 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<sub>KOWWIN</sub>. 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.https://www.mdpi.com/1420-3049/28/1/166heterocycleslipophilicityTLCanti-androgensblood uric acid lowering compoundsprincipal component analysis |
| spellingShingle | Dawid Wardecki Małgorzata Dołowy Katarzyna Bober-Majnusz Josef Jampilek Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds Molecules heterocycles lipophilicity TLC anti-androgens blood uric acid lowering compounds principal component analysis |
| title | Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds |
| title_full | Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds |
| title_fullStr | Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds |
| title_full_unstemmed | Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds |
| title_short | Comparative Study of the Lipophilicity of Selected Anti-Androgenic and Blood Uric Acid Lowering Compounds |
| title_sort | comparative study of the lipophilicity of selected anti androgenic and blood uric acid lowering compounds |
| topic | heterocycles lipophilicity TLC anti-androgens blood uric acid lowering compounds principal component analysis |
| url | https://www.mdpi.com/1420-3049/28/1/166 |
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