A Comparative Study of the Lipophilicity of Metformin and Phenformin
The results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP...
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6613 |
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| author | Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz |
| author_facet | Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz |
| author_sort | Małgorzata Dołowy |
| collection | DOAJ |
| description | The results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP) and reversed-phase (RP) TLC systems. The retention parameters (R<sub>F</sub>, R<sub>M</sub>) obtained under different chromatographic conditions, i.e., various stationary and mobile phases in the NP-TLC and RP-TLC systems, were used to determine the lipophilicity parameter (R<sub>MW</sub>) of metformin and phenformin. This study confirms the poor lipophilicity of both metformin and phenformin. It can be stated that the optimization of chromatographic conditions, i.e., the kind of stationary phase and the composition of mobile phase, was needed to obtain the reliable value of the chromatographic lipophilicity parameter (R<sub>MW</sub>) in this study. The fewer differences in the R<sub>MW</sub> values of both biguanide derivatives were ensured by the RP-TLC system composed of RP2, RP18, and RP18W plates and the mixture composed of methanol, propan-1-ol, and acetonitrile as an organic modifier compared to the NP-TLC analysis. The new calculation procedures for logP of drugs based on topological indices <sup>0</sup>χ<sup>ν</sup>, <sup>0</sup>χ, <sup>1</sup>χ<sup>ν</sup>, M, and M<sup>ν</sup> may be a certain alternative to other algorithms as well as the TLC procedure performed under optimized chromatographic conditions. The knowledge of different lipophilicity parameters of the studied biguanides can be useful in the future design of novel and more therapeutically effective metformin and phenformin formulations for antidiabetic and possible anticancer treatment. Moreover, the topological indices presented in this work may be further used in the QSAR study of the examined biguanides. |
| first_indexed | 2024-03-10T05:56:17Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:56:17Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e580766168184b329f3c02582ddd49e32023-11-22T21:23:56ZengMDPI AGMolecules1420-30492021-10-012621661310.3390/molecules26216613A Comparative Study of the Lipophilicity of Metformin and PhenforminMałgorzata Dołowy0Josef Jampilek1Katarzyna Bober-Majnusz2Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellonska 4, 41-200 Sosnowiec, PolandDepartment of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 842 15 Bratislava, SlovakiaDepartment of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellonska 4, 41-200 Sosnowiec, PolandThe results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP) and reversed-phase (RP) TLC systems. The retention parameters (R<sub>F</sub>, R<sub>M</sub>) obtained under different chromatographic conditions, i.e., various stationary and mobile phases in the NP-TLC and RP-TLC systems, were used to determine the lipophilicity parameter (R<sub>MW</sub>) of metformin and phenformin. This study confirms the poor lipophilicity of both metformin and phenformin. It can be stated that the optimization of chromatographic conditions, i.e., the kind of stationary phase and the composition of mobile phase, was needed to obtain the reliable value of the chromatographic lipophilicity parameter (R<sub>MW</sub>) in this study. The fewer differences in the R<sub>MW</sub> values of both biguanide derivatives were ensured by the RP-TLC system composed of RP2, RP18, and RP18W plates and the mixture composed of methanol, propan-1-ol, and acetonitrile as an organic modifier compared to the NP-TLC analysis. The new calculation procedures for logP of drugs based on topological indices <sup>0</sup>χ<sup>ν</sup>, <sup>0</sup>χ, <sup>1</sup>χ<sup>ν</sup>, M, and M<sup>ν</sup> may be a certain alternative to other algorithms as well as the TLC procedure performed under optimized chromatographic conditions. The knowledge of different lipophilicity parameters of the studied biguanides can be useful in the future design of novel and more therapeutically effective metformin and phenformin formulations for antidiabetic and possible anticancer treatment. Moreover, the topological indices presented in this work may be further used in the QSAR study of the examined biguanides.https://www.mdpi.com/1420-3049/26/21/6613metforminphenforminlipophilicitytopological indiceslogP |
| spellingShingle | Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz A Comparative Study of the Lipophilicity of Metformin and Phenformin Molecules metformin phenformin lipophilicity topological indices logP |
| title | A Comparative Study of the Lipophilicity of Metformin and Phenformin |
| title_full | A Comparative Study of the Lipophilicity of Metformin and Phenformin |
| title_fullStr | A Comparative Study of the Lipophilicity of Metformin and Phenformin |
| title_full_unstemmed | A Comparative Study of the Lipophilicity of Metformin and Phenformin |
| title_short | A Comparative Study of the Lipophilicity of Metformin and Phenformin |
| title_sort | comparative study of the lipophilicity of metformin and phenformin |
| topic | metformin phenformin lipophilicity topological indices logP |
| url | https://www.mdpi.com/1420-3049/26/21/6613 |
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