Fluorination in aqueous media with elemental fluorine: The synthesis of (F-18)2-FDG
Continued emphasis on the use of F-18 labeled 2-deoxy-2-fluor-D-glucose (2-FDG) for the determination of local organ glucose metabolism in normal and diseased states with PET provides the impetus for investigation of more facile procedures for synthesizing this important radiopharmaceutical. The authors report herein the regio- and stereo-selective addition of fluorine across a double bond, i.e. D-glucal (1), in aqueous media to yield 2-FDG. 2-FDG was prepared by bubbling 0.2% fluorine in neon into an aqueous solution containing an equimolar amount of glucal at room temperature. Hydrolysis of the resultant fluorinated product mixture with 1 N HCL (120/sup 0/C, 15m) followed by chromatographic purification, using an ion retardation resin-alumina column gave 2-FDG in about 60% yield. The final product was identified by TLC, /sup 19/F NMR (94.1 MHz, deuterium oxide, hexafluorobezene (external standard) delta + 32.81 ppm (..cap alpha..-anomer, 48.5%) and + 32.51 ppm (..beta..-anomer, 51.5%)), and by its conversion to the corresponding 6-phosphate with yeast hexokinase as shown by HPLC. This method was extended to the synthesis of (F-18)2-FDG. (F-18)2-FDG was similarly prepared as described above from (F-18)fluorine in radiochemical yields of 25-30% (50-60% of theoretical maximum) with a processing time of 30 min after EOB. This synthesis of (F-18)2-FDG provides simplification, reduced processing time, and a radiochemical yield that is competitive with other methods recently described.
- Research Organization:
- UCLA School of Medicine, Los Angeles, CA
- OSTI ID:
- 6793583
- Journal Information:
- J. Nucl. Med.; (United States), Vol. 25:5
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
FLUORINE 18
RADIOCHEMISTRY
FLUORODEOXYGLUCOSE
CHEMICAL PREPARATION
LABELLING
AMBIENT TEMPERATURE
AQUEOUS SOLUTIONS
BENZENE
CHEMICAL REACTION YIELD
FLUORINATION
HYDROLYSIS
LIQUID COLUMN CHROMATOGRAPHY
METABOLISM
NMR SPECTRA
POSITRON COMPUTED TOMOGRAPHY
RADIOPHARMACEUTICALS
THIN-LAYER CHROMATOGRAPHY
ANTIMETABOLITES
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
COMPUTERIZED TOMOGRAPHY
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DISPERSIONS
DRUGS
EMISSION COMPUTED TOMOGRAPHY
FLUORINE ISOTOPES
HALOGENATION
HOURS LIVING RADIOISOTOPES
HYDROCARBONS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
LYSIS
MIXTURES
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
RADIOISOTOPES
SEPARATION PROCESSES
SOLUTIONS
SOLVOLYSIS
SPECTRA
SYNTHESIS
TOMOGRAPHY
YIELDS
550601* - Medicine- Unsealed Radionuclides in Diagnostics
400202 - Isotope Effects
Isotope Exchange
& Isotope Separation