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Hydrophobicity and haemolytic potential of oxo derivatives of cholic, deoxycholic and chenodeoxycholic acids

Authors
Journal
Steroids
0039-128X
Publisher
Elsevier
Publication Date
Volume
75
Issue
6
Identifiers
DOI: 10.1016/j.steroids.2010.02.008
Keywords
  • Oxo Derivatives Of Bile Acids
  • Haemolytic Potential
  • Hydrophobicity
  • Critical Micellar Concentration
Disciplines
  • Chemistry

Abstract

Abstract 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.

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