Synthesis and radioiodination of a nido-1,2-carboranyl derivative of 2-nitroimidazole

Nucl Med Biol. 1994 May;21(4):601-11. doi: 10.1016/0969-8051(94)90025-6.

Abstract

The synthesis of a nido-carboranyl congener of misonidazole, 1-(3'-nido-carboranyl-2'-hydroxy)propyl-2-nitroimidazole, has been carried out. Alternative methods of preparations were conducted to optimize the chemical yield, with a five step synthesis giving an overall yield (from 1,2-carborane) of 36%. A diastereomeric pair of nido-carboranyl compounds was obtained. The diastereomeric nido-carboranyl misonidazole congeners were (radio)iodinated to yield (> 90%) a mixture of diastereomeric compounds in which the iodine had bonded to a boron atom on the nido-carborane moiety. These compounds will be investigated for their application to boron neutron capture therapy (BNCT) and hypoxia imaging of cancer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Neutron Capture Therapy
  • Chromatography, High Pressure Liquid
  • Iodine Radioisotopes / chemistry*
  • Isotope Labeling / methods*
  • Misonidazole / analogs & derivatives*
  • Nitroimidazoles / chemical synthesis*
  • Stereoisomerism

Substances

  • Boron Compounds
  • Iodine Radioisotopes
  • Nitroimidazoles
  • 1-(3'-nido-carboranyl-2'-hydroxy)propyl-2-nitroimidazole
  • Misonidazole