Reactivity and selectivity of F2 towards 3,4,6-tri-O-acetyl-D-glucal in anhydrous HF: Synthesis of [18F]-2-fluoro-2-deoxy-ß-D-allose ([18F]2-FDßA) for the detection of breast tumor

FLUO 19

Raman Chirakal, chiraklr@mcmaster.ca1, Gary J. Schrobilgen, schrobil@mcmaster.ca2, Rezwan Ashique, ashique@hhsc.ca1, Donald W. Hughes, hughesd@mcmaster.ca2, Troy Farncombe, farncomb@hhsc.ca1, Chantal Saab1, Tracey Truman3, and Renee Labiris, labir@mcmaster.ca3. (1) Department of Nuclear Medicine, Hamilton Health Sciences, 1200 Main Street West, Hamilton, ON L8N 3Z5, Canada, (2) Department of Chemistry, McMaster University, 1280 Main St. West, Hamilton, ON L8S 4M1, Canada, (3) Department of Medicine, McMaster University, 1280 Main St. West, Hamilton, ON L8S 4L8, Canada
There has been a growing interest in the investigation of the biological properties of rare sugars, which are monosaccharides that are rarely distributed in nature. D-allose, a rare sugar and a C3 epimer of D-glucose, has been shown to have an inhibitory effect on the production of reactive oxygen species and on the cancer cell proliferation. We have developed two-step, regio- and stereoselective syntheses of [19F]- and [18F]-2-fluoro-2-deoxy-ß-D-allose by the direct fluorination of 3,4,6-tri-O-acetyl-D-glucal in anhydrous HF at -60 °C. We report in this paper the chromatographic properties of 2-FDßA and its characterization by 1H, 13C, and 19F NMR spectroscopy as well as by 2D-NMR spectroscopy. We will also present the biodistribution data of [18F]2-FDßA in FVB mice (controls) and a murine tumor model (Polynoma Middle T) showing that [18F]2-FDßA might be an alternative positron emission tomography (PET) radiotracer to [18F]2-fluoro-2-deoxy-D-glucose (2-FDG) for the diagnosis of human breast cancer.
 

Fluorinated Heterocycles
1:30 PM-4:55 PM, Monday, 11 September 2006 San Francisco Marriott -- Salon 5, Oral

Division of Fluorine Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006