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Thermodynamics of transfer and partition of 3,5-diamino-1-phenyl-1,2,4-triazole in the 1-octanol/water biphasic system

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Abstract

In this paper, we focus for the first time on thermodynamics of transfer of 3,5-diamino-1-phenyl-1,2,4-triazole (DAPT) from water to liquid 1-octanol which is considered in pharmaceutical chemistry as an appropriate model of a lipid-like environment for studying a passive membrane transport of various drugs. The enthalpies of solution of DAPT have been determined calorimetrically in both solvents at 298.15, 308.15 and 328.15 K. The partition coefficients (P) have been obtained in the 1-octanol/water biphasic system at 298.15 and 328.15 K using a classical isothermic saturation method. Standard thermodynamic functions of DAPT transfer from water to a lipid-like phase have been calculated via the Gibbs–Helmholtz equation using the temperature dependence of the standard enthalpies of solution and the partition coefficient at the reference temperature of 298.15 K. We have found that the enthalpic term favours the solute transfer both at lower and elevated temperatures, whereas the entropic one contributes in the opposite manner. The free energy of transfer remains negative for all the temperature range studied indicating rather appreciable affinity of a potential drug towards a lipid-like environment. The comparison of the experimental and calculated P values indicates that our approach is able to predict with a good accuracy the behaviour of the 1,2,4-triazole derivatives for the physiological temperature range.

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Acknowledgements

This work was supported by the Russian Science Foundation (Grant 18-73-00217).

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Authors and Affiliations

  1. G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1, Academicheskaya str., Ivanovo, Russia, 153045

    Andrey V. Kustov & Nataliya L. Smirnova

  2. Institute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, 7, Sheremetevsky av., Ivanovo, Russia, 153000

    Tatyana V. Kustova

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  1. Andrey V. Kustov
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  2. Nataliya L. Smirnova
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  3. Tatyana V. Kustova
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Correspondence to Andrey V. Kustov.

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Kustov, A.V., Smirnova, N.L. & Kustova, T.V. Thermodynamics of transfer and partition of 3,5-diamino-1-phenyl-1,2,4-triazole in the 1-octanol/water biphasic system. J Therm Anal Calorim 147, 1513–1517 (2022). https://doi.org/10.1007/s10973-020-10513-4

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