Synthesis and radioiodination of a nido-1,2-carboranyl derivative of 2-nitroimidazole.
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.
Wilbur
D S
DS
Department of Radiation Oncology, University of Washington, Seattle 98195, USA.
Hamlin
D K
DK
Livesey
J C
JC
Srivastava
R R
RR
Laramore
G E
GE
Griffin
T W
TW
D001896:Boron Compounds / Q000138:chemical synthesis*; D016754:Boron Neutron Capture Therapy; D002851:Chromatography, High Pressure Liquid; D007457:Iodine Radioisotopes / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods*; D008920:Misonidazole / Q000031:analogs & derivatives*; D009593:Nitroimidazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001896:Boron Compounds; D007457:Iodine Radioisotopes; D009593:Nitroimidazoles; C107827:1-(3'-nido-carboranyl-2'-hydroxy)propyl-2-nitroimidazole; D008920:Misonidazole