Hydrophobicity and haemolytic potential of oxo derivatives of cholic, deoxycholic and chenodeoxycholic acids.
The objective of this work was to study the effect of structure of bile acids on their membranolytic potential and extent of overlapping of the information about the membranolytic potential of bile acids and their physico-chemical parameters, namely: retention index R(M0) (as a measure of bile acid hydrophobicity, reversed-phase thin-layer chromatography (RPTLC)), lecithin solubilisation (measure of the interaction of bile acids with phospholipids) and critical micellar concentration (CMC). It was found that bile acid concentrations at 100% lysis of erythrocyte membranes is described best by their CMC values, whereas at 50% lysis the parameter used is lecithin solubilisation. This indicates that different mixed micelles are formed in the membrane lysis at lower and higher concentrations of bile acids. Replacement of the hydroxyl (OH) group in the bile acid molecule with an oxo group yields derivatives with lowered hydrophobicity, power of lecithin solubilisation, tendency for self-aggregation as well as the membranolytic activity.
Posa
Mihalj
M
Department of Pharmacy, Faculty of Medicine, University of Novi Sad, Hajduk Veljka 3, 21000 Novi Sad, Serbia. mihaljp@uns.ac.rs
Kuhajda
Ksenija
K
D000818:Animals; D002635:Chenodeoxycholic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002756:Cholagogues and Choleretics / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019826:Cholic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003840:Deoxycholic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004912:Erythrocytes / Q000166:cytology / Q000187:drug effects; D005765:Gastrointestinal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006461:Hemolysis / Q000187:drug effects*; D057927:Hydrophobic and Hydrophilic Interactions; D054709:Lecithins / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011817:Rabbits
D002756:Cholagogues and Choleretics; D005765:Gastrointestinal Agents; D054709:Lecithins; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D019826:Cholic Acid