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https://doi.org/10.5599/admet.760

Estimation of the octanol-water distribution coefficient of basic compounds by a cationic microemulsion electrokinetic chromatography system

Alejandro Fernández-Pumarega ; Departament d’Enginyeria Química i Química Analítica and Institut de Biomedicina (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain
Belén Martín-Sanz ; Departament d’Enginyeria Química i Química Analítica and Institut de Biomedicina (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain
Susana Amézqueta orcid id orcid.org/0000-0001-8976-467X ; Departament d’Enginyeria Química i Química Analítica and Institut de Biomedicina (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain
Elisabet Fuguet ; Departament d’Enginyeria Química i Química Analítica and Institut de Biomedicina (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain
Marti Rosés ; Departament d’Enginyeria Química i Química Analítica and Institut de Biomedicina (IBUB), Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain


Puni tekst: engleski pdf 1.051 Kb

str. 98-112

preuzimanja: 293

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Sažetak

The octanol-water partition coefficient (Po/w), or the octanol-water distribution coefficient (Do/w) for ionized compounds, is a key parameter in the drug development process. In a previous work, this parameter was estimated through the retention factor measurements in a sodium dodecyl sulfate (SDS) - microemulsion electrokinetic chromatography (MEEKC) system for acidic compounds. Nonetheless, when ionized basic compounds were analyzed, undesirable ion pairs were formed with the anionic surfactant and avoided a good estimation of log Do/w. For this reason, an alternative MEEKC system based on a cationic surfactant has been evaluated to estimate Po/w or Do/w of neutral compounds and ionized bases. To this end, it has been characterized through the solvation parameter model (SPM) and compared to the octanol-water partition system. Results pointed out that both systems show a similar partition behavior. Hence, the log Po/w of a set of neutral compounds has been successfully correlated against the logarithm of the retention factor (log k) determined in this MEEKC system. Then, the log Do/w of 6 model bases have been estimated at different pH values and they have been compared to data from the literature, determined by the reference shake-flask and potentiometric methods. Good agreement has been observed between the literature and the estimated values when the base is neutral or partially ionized (up to 99 % of ionization).

Ključne riječi

Lipophilicity; log Po/w; log Do/w; MEEKC; ionized bases; solvation parameter model; microemulsion; system surrogation

Hrčak ID:

235015

URI

https://hrcak.srce.hr/235015

Datum izdavanja:

4.3.2020.

Posjeta: 732 *