Biopartitioning micellar chromatography under different conditions: Insight into the retention mechanism and the potential to model biological processes

Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry

“…For all compounds under study, the log k MLC values were higher than log k W-IAM but lower than log k W . In another example, the lipophilicity of a set of 88 compounds was evaluated using IAM and MLC [203]. Here, the obtained log k MLC values covered a narrower range than the obtained log k W-IAM values (log k W-IAM range: from −1.15 to 3.98, log k MLC range: from 1.84 to 3.98).…”

“…In MLC, the micellar aggregates act as partition sites in the mobile phase, while the surfactant monomers present in the mobile phase modify the stationary phase either by both hydrophobic and/or silanophilic adsorption [203]. Due to the amphiphilic character of surfactants, the micellar mobile phase mimics the phospholipidic bilayer structure of biological membranes, while the modified stationary phase mimics not only the ordered array of the hydrophobic chains of phospholipids, mainly through the C18 carbon chains but also the polar heads of phospholipids, mainly through the adsorbed surfactant monomers [214].…”

“…During the elution, the solute can establish interactions with the micellar core, the micellar surface, the polar head of the surfactant bound to the stationary phase, and the alkyl chains bound to the stationary [194]. Therefore, solute retention involves the establishment of two different equilibriums: one between the bulk aqueous phase and the surfactant-coated stationary phase and another between the aqueous phase and the micelles [203]. The outcome index of MLC (log k MLC ) is a metric of anisotropic lipophilicity as it depends on hydrophobic, electronic, and steric interactions [215].…”

“…The outcome index of MLC (log k MLC ) is a metric of anisotropic lipophilicity as it depends on hydrophobic, electronic, and steric interactions [215]. Due to its similarity with biological membranes and extracellular fluids, MLC is also known as biopartitioning micellar chromatography [203].…”

Quantitative Retention (Structure)–Activity Relationships in Predicting the Pharmaceutical and Toxic Properties of Potential Pesticides

“…Surfactant monomers modify the surface phase as a result of the hydrophobic interactions between the tail of the surfactant and the alkyl chain. Molecular interactions present in this system, i.e., solute association with the polar head of the surfactant, solute penetration into the micelle core, and solute interactions with adsorbed surfactant and alkyl chains, affect retention by three different equilibria, which are (1) the solute distribution between the micelle (micellar pseudophase) and the bulk phase, (2) the solute partition between the stationary phase modified by the surfactant and the bulk phase, and (3) the direct transfer of solute molecules between the surfactant-modified surface and the micelle [ 17 , 18 , 19 , 20 , 21 ].…”