3-O-phosphate ester conjugates of 17-β-O-{1-[2-carboxy-(2-hydroxy-4-methoxy-3-carboxamido)anilido]ethyl}1,3,5(10)-estratriene as novel bone-targeting agents

Bioorg Med Chem Lett. 2010 Dec 15;20(24):7450-3. doi: 10.1016/j.bmcl.2010.10.023. Epub 2010 Oct 13.

Abstract

A series of 3-O-phosphorylated analogs (4-10) of a novel bone-targeting estradiol analog (3) were synthesized after a thorough study of the reaction of 3 with a selection of phosphoryl chlorides under a variety of reaction conditions. Evaluation of these novel phosphate analogs for affinity for hydroxyapatite revealed that they bind with equal or higher affinity when compared to the bone tissue accumulator, tetracycline.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bone and Bones / chemistry*
  • Durapatite / chemistry
  • Esters
  • Estradiol / analogs & derivatives*
  • Estradiol / chemical synthesis
  • Estradiol / pharmacology
  • Estrenes / chemistry*
  • Phosphates / chemistry*
  • Tetracycline / chemistry

Substances

  • 17-beta-O-(1-(2-carboxy-(2-hydroxy-4-methoxy-3-carboxamido)anilido)ethyl)1,3,5(10)-estratriene
  • Esters
  • Estrenes
  • Phosphates
  • Estradiol
  • Durapatite
  • Tetracycline