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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Autores principales:	Małgorzata Dołowy, Josef Jampilek, Katarzyna Bober-Majnusz
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	metformin phenformin lipophilicity topological indices logP Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/e580766168184b329f3c02582ddd49e3
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spelling	oai:doaj.org-article:e580766168184b329f3c02582ddd49e32021-11-11T18:35:04ZA Comparative Study of the Lipophilicity of Metformin and Phenformin10.3390/molecules262166131420-3049https://doaj.org/article/e580766168184b329f3c02582ddd49e32021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6613https://doaj.org/toc/1420-3049The 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.Małgorzata DołowyJosef JampilekKatarzyna Bober-MajnuszMDPI AGarticlemetforminphenforminlipophilicitytopological indiceslogPOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6613, p 6613 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	metformin phenformin lipophilicity topological indices logP Organic chemistry QD241-441
spellingShingle	metformin phenformin lipophilicity topological indices logP Organic chemistry QD241-441 Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz A Comparative Study of the Lipophilicity of Metformin and Phenformin
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.
format	article
author	Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz
author_facet	Małgorzata Dołowy Josef Jampilek Katarzyna Bober-Majnusz
author_sort	Małgorzata Dołowy
title	A Comparative Study of the Lipophilicity of Metformin and Phenformin
title_short	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_sort	comparative study of the lipophilicity of metformin and phenformin
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/e580766168184b329f3c02582ddd49e3
work_keys_str_mv	AT małgorzatadołowy acomparativestudyofthelipophilicityofmetforminandphenformin AT josefjampilek acomparativestudyofthelipophilicityofmetforminandphenformin AT katarzynabobermajnusz acomparativestudyofthelipophilicityofmetforminandphenformin AT małgorzatadołowy comparativestudyofthelipophilicityofmetforminandphenformin AT josefjampilek comparativestudyofthelipophilicityofmetforminandphenformin AT katarzynabobermajnusz comparativestudyofthelipophilicityofmetforminandphenformin
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A Comparative Study of the Lipophilicity of Metformin and Phenformin

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