Synthesis of a fluorine-18 labeled hypoxic cell sensitizer

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

OSTI ID:6591487

Jerabek, P A; Dischino, D D; Kilbourn, M R; Welch, M J

The objective of this work was to synthesize a positron emitting radiosensitizing agent as a potential in vivo marker of hypoxic regions within tumors, and ischemic areas of the heart and brain. The method involved radiochemical synthesis of fluorine-18 labeled 1-(2-nitro-imidazolyl)-3-fluoro-2-propanol via nucleophilic ring opening of 1-(2,3-epoxypropyl)2-nitro-imidzole by fluorine-18 labeled tetrabutylammonium fluoride (TBAF). Fluroine-18 TBAF was prepared by the exchange reaction of TBAF with aqueous flourine-18 produced by proton bombardment of enriched oxygen-18 water. The aqueous solution was evaporated carefully by azeotropic distillation with acetonitrile. The fluorine-18 labeled TBAF was taken up in N,N-dimethylacetamide or dimethysulfoxide, then reacted with the episode at 60C for 30 minutes. Separation and identification of the fluorine-18 labeled products by high performance liquid chromatography showed a radioactive peak with a retention time identical to that of 1-(2-nitro-1-imidazolyl)-3-fluoro-2-propanol and a second radioactive peak with a retention time three minutes longer in addition to unreacted fluorine-18 labeled TBAF. The second radioactive peak may represent fluorine-18 labeled 1-2-nitro-1-imidazolyl)-2-fluoro-3-propanol. The average radiochemical yield from reactions run in N,N-dimethylacetamide using 20 micromoles of TBAF and 1-2 mg of the epoxide was l7% in a synthesis time of about 40 minutes. The synthesis of fluorohydrins by the reaction of fluorine-18 labeled TBAF on epoxides represents a new method for the preparation of fluorine-18 labeled fluorohydrins.

• Research Organization: Washington Univ. School of Medicine, St. Louis, MO
• OSTI ID: 6591487
• Report Number(s): CONF-840619-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 25:5
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ALKYLATED AROMATICS
ANOXIA
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
BRAIN
CARDIOVASCULAR DISEASES
CARDIOVASCULAR SYSTEM
CENTRAL NERVOUS SYSTEM
CHEMICAL PREPARATION
CHEMISTRY
DISEASES
DRUGS
EPOXIDES
FLUORINE 18
FLUORINE ISOTOPES
HEART
HOURS LIVING RADIOISOTOPES
ISCHEMIA
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MEDICINE
NEOPLASMS
NERVOUS SYSTEM
NUCLEAR MEDICINE
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANS
RADIOCHEMISTRY
RADIOISOTOPES
RADIOLOGY
RADIOPHARMACEUTICALS
RADIOSENSITIVITY
RADIOSENSITIZERS
RADIOTHERAPY
SYNTHESIS
THERAPY
VASCULAR DISEASES