Improved synthesis of 17β-hydroxy-16α-iodo-wortmannin, 17β-hydroxy-16α-iodoPX866, and the [(131)I] analogue as useful PET tracers for PI3-kinase

Bioorg Med Chem. 2013 Sep 1;21(17):5182-7. doi: 10.1016/j.bmc.2013.06.036. Epub 2013 Jun 27.

Abstract

An improved method for the synthesis of 17β-hydroxy-16α-iodo-wortmannin along with the first synthesis of 17β-hydroxy-16α-iodoPX866 and [(131)I] radiolabeled 17β-hydroxy-16α-[(131)I]iodo-wortmannin, as potential PET tracers for PI3K was also described. The differences between wortmannin and its iodo analogue were compared by covalently docking each structure to L833 in PI3K.

Keywords: 17β-Hydroxy-16α-[(131)I]iodowortmannin; 17β-Hydroxy-16α-iodoPX866; 17β-Hydroxy-16α-iodowortmannin; LYDLNTRBZQFQTG-RUXBYQPCSA-N; OWEYHVVHIWKFGJ-TUYZGLGGSA-N; PI3 kinase; Positron emission tomography (PET) imaging.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Androstadienes / chemical synthesis*
  • Androstadienes / chemistry*
  • Binding Sites
  • Gonanes / chemical synthesis*
  • Gonanes / chemistry
  • Iodine Radioisotopes / chemistry
  • Isotope Labeling
  • Molecular Docking Simulation
  • Phosphatidylinositol 3-Kinase / chemistry
  • Phosphatidylinositol 3-Kinase / metabolism
  • Positron-Emission Tomography
  • Protein Structure, Tertiary
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Wortmannin

Substances

  • 17beta-hydroxy-16alpha-iodo-wortmannin
  • 17beta-hydroxy-16alpha-iodoPX866
  • Androstadienes
  • Gonanes
  • Iodine Radioisotopes
  • Radiopharmaceuticals
  • Phosphatidylinositol 3-Kinase
  • Wortmannin