title: Global optimization of cholic acid aggregates.
abstract: In spite of recent investigations into the potential pharmaceutical importance of bile acids as drug carriers, the structure of bile acid aggregates is largely unknown. Here, we used global optimization techniques to find the lowest energy configurations for clusters composed between 2 and 10 cholate molecules, and evaluated the relative stabilities of the global minima. We found that the energetically most preferred geometries for small aggregates are in fact reverse micellar arrangements, and the classical micellar behaviour (efficient burial of hydrophobic parts) is achieved only in systems containing more than five cholate units. Hydrogen bonding plays a very important part in keeping together the monomers, and among the size range considered, the most stable structure was found to be the decamer, having 17 hydrogen bonds. Molecular dynamics simulations showed that the decamer has the lowest dissociation propensity among the studied aggregation numbers.
authors.affiliation: Department of Chemical Informatics, Faculty of Education, University of Szeged, Boldogasszony sgt. 6, H-6725, Szeged, Hungary.
authors.forename: Balázs
authors.initials: B
authors.lastname: Jójárt
authors.affiliation: Department of Chemical Informatics, Faculty of Education, University of Szeged, Boldogasszony sgt. 6, H-6725, Szeged, Hungary.
authors.forename: Béla
authors.initials: B
authors.lastname: Viskolcz
authors.affiliation: University of Novi Sad, Faculty of Medicine, Department of Pharmacy, Novi Sad, Serbia.
authors.forename: Mihalj
authors.initials: M
authors.lastname: Poša
authors.affiliation: Department of Chemical Informatics, Faculty of Education, University of Szeged, Boldogasszony sgt. 6, H-6725, Szeged, Hungary.
authors.forename: Szilard N
authors.initials: SN
authors.lastname: Fejer
mesh_terms: D001647:Bile Acids and Salts / Q000737:chemistry*; D019826:Cholic Acid / Q000737:chemistry*; D004337:Drug Carriers; D006801:Humans; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D056004:Molecular Dynamics Simulation
chemical_list: D001647:Bile Acids and Salts; D004337:Drug Carriers; D008823:Micelles; D019826:Cholic Acid