Evaluation of the suitability of chromatographic systems to predict human skin permeation of neutral compounds

Hidalgo-Rodríguez, Marta; Soriano-Meseguer, Sara; Fuguet, Elisabet; Ràfols, Clara; Rosés, Martı́

doi:10.1016/j.ejps.2013.04.005

Cited by 27 publications

(18 citation statements)

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“…The addition of the cosurfactant produced important differences between the mobility values obtained with or without it, although the reason for these differences has not been systematically studied. Taking into account that the retention factor of a substance in a given system is often used to estimate other of its properties, such as logPo/w [8][9][10][11] or biopartitioning parameters [20][21][22][23][24], it is very important to ensure it is determined correctly.…”

Section: Introductionmentioning

confidence: 99%

Determination of the retention factor of ionizable compounds in microemulsion electrokinetic chromatography

Fernández-Pumarega

Amézqueta

Fuguet

et al. 2019

Analytica Chimica Acta

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Determination of the retention factor of ionized compounds in microemulsion electrokinetic chromatography requires two mobility measurements at the same pH: one in the presence of the microemulsion and another in plain buffer. However, it has been observed that in some cases subtracting one mobility from another determined in a different medium leads to negative retention factors, which makes no sense from a chemical point of view. This indicates that there is some error in the process which has a direct impact when retention factors are used for further applications. Here, we evaluate how the components of the microemulsion confer different properties to the buffer medium, particularly varying the viscosity parameter (which is inversely related to mobility). Whereas sodium dodecyl sulfate, the surfactant used in the microemulsion, has little effect on the medium viscosity (only an increase of 5%-6%), the presence of 1-butanol, used as a stabilizer, increases it by around 30%. Meanwhile, heptane, which is used as an oil, provokes a slight decrease. Consequently, the mobilities obtained in the microemulsion system are shifted to higher values (less negative mobilities) compared to mobilities obtained in the aqueous buffer, and so one cannot be directly subtracted from the other. Since the microemulsion-buffer medium cannot be directly reproduced, we propose a correction that takes into account the variation of viscosities. This is determined from the electrophoretic mobility of the benzoate ion. As this ion does not interact with the microemulsion, the ratio of its mobilities (measured in plain buffer and microemulsion) is equivalent to the ratio of viscosities, and can be used as the correction factor for other measurements. Thus, mobilities in buffer and microemulsion media are placed on the same scale, overcoming the errors in retention factor determination.

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Section: Introductionmentioning

confidence: 99%

Determination of the retention factor of ionizable compounds in microemulsion electrokinetic chromatography

Fernández-Pumarega

Amézqueta

Fuguet

et al. 2019

Analytica Chimica Acta

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“…The EKC system was substantially different compared to systems based on, for example, the traditional octanol‐water partition coefficient and provided a basis for the prediction of skin penetration. In another study, Roses group compared HPLC, MEKC, and the octanol‐water partition coefficient for modeling skin penetration . They found that the best correlation of skin permeation of selected hormones and pesticides was achieved by HPLC on an RP‐18 column compared to the other systems including MEKC employing SDS or sodium taurocholate micelles.…”

Section: Separation and Analysis Of Small Molecules And Nonbiotechnolmentioning

confidence: 99%

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis

et al. 2014

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Since the introduction about 30 years ago, CE techniques have gained a significant impact in pharmaceutical analysis. The present review covers recent advances and applications of CE for the analysis of pharmaceuticals. Both small molecules and biomolecules such as proteins are considered. The applications range from the determination of drug-related substances to the analysis of counterions and the determination of physicochemical parameters. Furthermore, general considerations of CE methods in pharmaceutical analysis are described.

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“…Liquid chromatography is frequently used to investigate physicochemical properties and biological activity of solutes, including their skin permeability. The chromatographic techniques used to predict the ability of molecules to cross the skin barrier include normal and reversed-phase thin layer chromatography [ 21 , 22 ], immobilized artificial membrane (IAM) column chromatography [ 23 , 24 , 25 , 26 ], RP-18 column chromatography [ 24 , 25 ], column chromatography on a unique stationary phase based on immobilized keratin [ 27 ], and biopartitioning micellar chromatography (BMC) [ 28 , 29 , 30 ]. The skin permeability coefficient K p is connected with the chromatographic retention parameters log k or R M 0 (obtained for column and thin layer chromatography, respectively) via linear or reverse parabolic relationships [ 22 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

“…The skin permeability coefficient K p is connected with the chromatographic retention parameters log k or R M 0 (obtained for column and thin layer chromatography, respectively) via linear or reverse parabolic relationships [ 22 , 26 ]. Chromatographic retention parameters are used either as sole skin permeability predictors, or they are combined with additional descriptors (log P ow , V M , M w or M Pt ) [ 23 , 24 , 28 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

RP-18 TLC Chromatographic and Computational Study of Skin Permeability of Steroids

2021

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The skin permeability of steroids, as investigated in this study, is important because some of these compounds are, or could, be used in preparations applied topically. Several models of skin permeability, involving thin layer chromatographic and calculated descriptors, were generated and validated using Kp reference values obtained in silico and then tested on a group of solutes whose experimental Kp values could be found (log Kpexp). The study established that the most applicable log Kp model is based on RP-18 thin layer chromatographic data (RM) and the calculated descriptors VM (molar volume) and PSA (polar surface area). Two less efficient, yet simple, equations based on PSA or VM combined with HD (H-donor count) can be used with caution for rapid, rough estimations of compounds’ skin permeability prior to their chemical synthesis.

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Evaluation of the suitability of chromatographic systems to predict human skin permeation of neutral compounds

Cited by 27 publications

References 50 publications

Determination of the retention factor of ionizable compounds in microemulsion electrokinetic chromatography

Determination of the retention factor of ionizable compounds in microemulsion electrokinetic chromatography

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis

RP-18 TLC Chromatographic and Computational Study of Skin Permeability of Steroids

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