Fluorination in aqueous media with elemental fluorine: The synthesis of (F-18)2-FDG

Journal Article · Sun Jan 01 04:00:00 EST 1984 · J. Nucl. Med.; (United States)

OSTI ID:6793583

Bida, G T; Satyamurthy, N; Barrio, J R

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), Journal Name: J. Nucl. Med.; (United States) Vol. 25:5; ISSN JNMEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202 -- Isotope Effects
Isotope Exchange
& Isotope Separation
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
AMBIENT TEMPERATURE
ANTIMETABOLITES
AQUEOUS SOLUTIONS
AROMATICS
BENZENE
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
COMPUTERIZED TOMOGRAPHY
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DISPERSIONS
DRUGS
EMISSION COMPUTED TOMOGRAPHY
FLUORINATION
FLUORINE 18
FLUORINE ISOTOPES
FLUORODEOXYGLUCOSE
HALOGENATION
HOURS LIVING RADIOISOTOPES
HYDROCARBONS
HYDROLYSIS
ISOTOPES
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
LYSIS
METABOLISM
MIXTURES
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
POSITRON COMPUTED TOMOGRAPHY
RADIOCHEMISTRY
RADIOISOTOPES
RADIOPHARMACEUTICALS
SEPARATION PROCESSES
SOLUTIONS
SOLVOLYSIS
SPECTRA
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TOMOGRAPHY
YIELDS