Synthesis of a fluorine-18 labeled hypoxic cell sensitizer
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-; TRN: 87-018884
- Journal Information:
- J. Nucl. Med.; (United States), Vol. 25:5; Conference: 31. annual meeting of the Society of Nuclear Medicine, Los Angeles, CA, USA, 5 Jun 1984
- Country of Publication:
- United States
- Language:
- English
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38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
FLUORINE 18
RADIOCHEMISTRY
NEOPLASMS
RADIOSENSITIVITY
RADIOPHARMACEUTICALS
CHEMICAL PREPARATION
RADIOSENSITIZERS
ALKYLATED AROMATICS
ANOXIA
BRAIN
EPOXIDES
HEART
ISCHEMIA
ORGANIC FLUORINE COMPOUNDS
RADIOTHERAPY
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
CARDIOVASCULAR DISEASES
CARDIOVASCULAR SYSTEM
CENTRAL NERVOUS SYSTEM
CHEMISTRY
DISEASES
DRUGS
FLUORINE ISOTOPES
HOURS LIVING RADIOISOTOPES
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MEDICINE
NERVOUS SYSTEM
NUCLEAR MEDICINE
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANS
RADIOISOTOPES
RADIOLOGY
SYNTHESIS
THERAPY
VASCULAR DISEASES
550601* - Medicine- Unsealed Radionuclides in Diagnostics
400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials