Myocardial imaging agents: synthesis, characterization, and evaluation of (Z)- and (Z,E)-18-/sup 82/Brbromo-5-tellura-17-octadecenoic acids

Journal Article · Mon Apr 01 04:00:00 EST 1985 · J. Med. Chem.; (United States)

DOI:https://doi.org/10.1021/jm00382a003· OSTI ID:5650322

Srivastava, P C; Knapp, Jr, F F; Callahan, A P; Owen, B A; Kabalka, G W; Sastry, K A

The effects of replacement of radioiodide with radiobromide on the biological properties of a model vinyl halide substituted tellurium fatty acid have been evaluated. The use of a facile radiobromination method involving the reaction of (/sup 82/Br)Br/sub 2/ with vinylmercuric bromide substrates has been investigated. Unexpectedly, both the cis- and trans- vinyl bromide products are formed as confirmed by chromatographic and spectral studies. With use of this technique, (E,Z)-1-(/sup 82/Br)bromo-13- iodo-1-tridecene was prepared and used as the substrate to prepare (E,Z)- 18-(/sup 82/Br)bromo-5-tellura-17-octadecenoic acid (13-E,Z), which was evaluated in rats. Both (/sup 82/Br)-13-E,Z and (/sup 82/Br)-13-Z, prepared by an established procedure using N-chorosuccinimide-Br- reaction with the trans-boronovinyl substrates, showed tissue distribution properties similar to those of (E)-18-(/sup 125/I)iodo-5-tellura-17-octadecenoic acid. These results demonstrate that replacement of I with Br and also the stereochemistry about the olefinic bond do not drastically affect heart uptake and retention.

• Research Organization: Oak Ridge National Lab., TN
• OSTI ID: 5650322
• Journal Information: J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 28:4; ISSN JMCMA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
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550601 -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ANIMALS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
BODY
BROMINE 82
BROMINE COMPOUNDS
BROMINE ISOTOPES
CARBOXYLIC ACIDS
CARDIOVASCULAR SYSTEM
CHEMICAL PREPARATION
CHEMISTRY
COMPARATIVE EVALUATIONS
COUNTING TECHNIQUES
DAYS LIVING RADIOISOTOPES
DISTRIBUTION
DRUGS
EVALUATION
HALOGEN COMPOUNDS
HEART
INTERMEDIATE MASS NUCLEI
ISOTOPES
LABELLED COMPOUNDS
MAMMALS
MONOCARBOXYLIC ACIDS
MUSCLES
MYOCARDIUM
NUCLEI
OCTADECANOIC ACID
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RADIOCHEMISTRY
RADIOISOTOPE SCANNING
RADIOISOTOPES
RADIOPHARMACEUTICALS
RATS
RETENTION
RODENTS
STEREOCHEMISTRY
SYNTHESIS
TELLURIUM COMPOUNDS
TISSUE DISTRIBUTION
UPTAKE
VERTEBRATES