Synthesis of new hypoxia markers EF1 and [18F]-EF1.
We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N- (3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120 degrees C. Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET).
Kachur
A V
AV
Department of Radiation Oncology, University of Pennsylvania, Philadelphia 19104, USA.
Dolbier
W R
WR
Evans
S M
SM
Shiue
C Y
CY
Shiue
G G
GG
Skov
K A
KA
Baird
I R
IR
James
B R
BR
Li
A R
AR
Roche
A
A
Koch
C J
CJ
D015415:Biomarkers / Q000032:analysis; D005462:Fluorine Radioisotopes / Q000737:chemistry; D000860:Hypoxia / Q000175:diagnosis* / Q000378:metabolism; D007553:Isotope Labeling / Q000379:methods; D009593:Nitroimidazoles / Q000138:chemical synthesis*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D014055:Tomography, Emission-Computed
C402596:2-(2-nitroimidazol-1H-yl)-N-(3-fluoropropyl)acetamide; D015415:Biomarkers; D005462:Fluorine Radioisotopes; D009593:Nitroimidazoles; D019275:Radiopharmaceuticals