Synthesis, characterization and biological activity of hydroxyl-bisphosphonic analogs of bile acids

Eur J Med Chem. 2012 Jun:52:221-9. doi: 10.1016/j.ejmech.2012.03.020. Epub 2012 Mar 19.

Abstract

Bisphosphonates (BPs) are now the most widely used drugs for diseases associated with increased bone resorption, such as osteoporosis, and tumor bone diseases. A significant drawback of the BPs is their poor oral absorption that is enhanced by the presence of bile acid substituents in the bisphosphonate framework, with no toxic effects. A straightforward synthesis of bile acid-containing hydroxy-bisphosphonates and a full characterization of these pharmaceutically important molecules, including an evaluation of affinity and the mechanism of binding to hydroxyapatite, is presented. The biological activity of bile acid-containing bisphosphonate salts was determined using the neutral-red assay on the L929 cell line and primary cultures of osteoclasts. The bioactivity of the new compounds was found superior than bisphosphonates of established activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absorption
  • Animals
  • Apoptosis / drug effects
  • Bile Acids and Salts / chemistry*
  • Cell Line
  • Chemistry Techniques, Synthetic*
  • Diphosphonates / chemical synthesis*
  • Diphosphonates / chemistry
  • Diphosphonates / metabolism
  • Diphosphonates / pharmacology*
  • Durapatite / metabolism
  • Gastrointestinal Tract / metabolism
  • Hydrophobic and Hydrophilic Interactions
  • Hydroxides / chemistry*
  • Mice
  • Osteoclasts / cytology
  • Osteoclasts / drug effects
  • Osteogenesis / drug effects

Substances

  • Bile Acids and Salts
  • Diphosphonates
  • Hydroxides
  • hydroxide ion
  • Durapatite