title: Synthesis, aggregation behavior and cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid).
abstract: Synthesis, aggregation behavior and in vitro cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid, EPCA) are reported. The synthesis of this unnatural epimer of pythocholic acid (3 alpha,12 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, PCA) involves a series of simple and selective chemical transformations with an overall yield of 21% starting from readily available cholic acid (CA). The critical micellar concentration (CMC) of 16-epi-pythocholate in aqueous media was determined using pyrene as a fluorescent probe. In vitro cholesterol solubilization ability was evaluated using anhydrous cholesterol and results were compared with those of other natural di- and trihydroxy bile acids. These studies showed that 16-epi-pythocholic acid (16 beta-hydroxy-deoxycholic acid) behaves similar to cholic acid (CA) and avicholic acid (3 alpha,7 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, ACA) in its aggregation behavior and cholesterol dissolution properties.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. nonappa@jyu.fi
authors.lastname: Nonappa
authors.forename: Uday
authors.initials: U
authors.lastname: Maitra
mesh_terms: D001647:Bile Acids and Salts / Q000138:chemical synthesis* / Q000737:chemistry*; D002784:Cholesterol / Q000737:chemistry*; D019826:Cholic Acid / Q000737:chemistry*; D002793:Cholic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012995:Solubility
chemical_list: C551522:3,12,16-trihydroxycholan-24-oic acid; D001647:Bile Acids and Salts; D002793:Cholic Acids; D002784:Cholesterol; D019826:Cholic Acid