RT Journal Article
T1 Highly Hydrophilic and Lipophilic Derivatives of Bile Salts
A1 Vázquez Tato, María del Pilar
A1 Seijas Vázquez, Julio Antonio
A1 Meijide del Río, Francisco Ángel
A1 Fraga López, Francisco
A1 Frutos del Río, Santiago de
A1 Miragaya Otero, Javier
A1 Trillo Novo, Juan Ventura
A1 Jover Ramos, Aida
A1 Soto Tellini, Victor Hugo
A1 Vázquez Tato, José
K1 Bile acids and salts
K1 Partition coefficient
K1 Isothermal titration calorimetry
K1 Hydrophilic-lipophilic balance
K1 Lipophilicity
K1 Demicellization thermodynamics
AB Lipophilicity of 15 derivatives of sodium cholate, defined by the octan-1-ol/water partition coefficient (log P), has been theoretically determined by the Virtual log P method. These derivatives bear highly hydrophobic or highly hydrophilic substituents at the C3 position of the steroid nucleus, being linked to it through an amide bond. The difference between the maximum value of log P and the minimum one is enlarged to 3.5. The partition coefficient and the critical micelle concentration (cmc) are tightly related by a double-logarithm relationship (VirtuallogP=−(1.00±0.09)log(cmcmM)+(2.79±0.09)), meaning that the Gibbs free energies for the transfer of a bile anion from water to either a micelle or to octan-1-ol differ by a constant. The equation also means that cmc can be used as a measurement of lipophilicity. The demicellization of the aggregates formed by three derivatives of sodium cholate bearing bulky hydrophobic substituents has been studied by surface tension and isothermal titration calorimetry. Aggregation numbers, enthalpies, free energies, entropies, and heat capacities, ΔCP,demic, were obtained. ΔCP,demic, being positive, means that the interior of the aggregates is hydrophobic
PB MDPI
YR 2021
FD 2021
LK http://hdl.handle.net/10347/26740
UL http://hdl.handle.net/10347/26740
LA eng
NO Int. J. Mol. Sci. 2021, 22(13), 6684; https://doi.org/10.3390/ijms22136684
NO This work was funded by the Ministerio de Ciencia y Tecnología, Spain (Project MAT2017-86109P)
DS Minerva
RD 22 abr 2026