Effect of tellurium position on the myocardial uptake of radioiodinated 18-iodotellura-17-octadecenoic acid analogues

Journal Article · Sat Dec 31 23:00:00 EST 1983 · J. Med. Chem.; (United States)

DOI:https://doi.org/10.1021/jm00367a011· OSTI ID:6549123

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

The effect of tellurium (Te) position on myocardial specificity and retention of fatty acids in which radioiodide is stabilized as a trans-(E)-vinyl iodide has been evaluated in rats. Five analogues of 18-iodo-17-octadecenoic acid (ICH . CH-R-Te-R'-COOH) with Te at positions 5, 7, 9, 11, and 13 were prepared by coupling of a trans-diiodoalkene (ICH . CH-R-I) with the requisite sodium ((alkoxycarbonyl)alkyl)telluride substrate (NaTe-R'-COOR''; R'' . Me or Et), followed by basic hydrolysis. By varying R and R', a series of analogues with a chain length of 18 carbon atoms was prepared. The telluride substrates were generated in situ by NaBH4 reduction of the corresponding ditellurides, and the diiodoalkenes were prepared by sodium iodide-chloramine-T treatment of the corresponding vinylboronic acids ((HO)2BCH . CH-R-I)). The vinylboronic acids were prepared by treatment of the terminal acetylenes (HC identical to C-R-I), synthesized from commercially available materials, with catecholborane. All new compounds were analyzed by TLC, NMR, MS, and elemental analyses. The /sup 125/I analogues ((E)-/sup 125/ICH . CH-R-Te-R'-COOH) were prepared in the same manner and evaluated in rats (four per group). Heart uptake and retention were dependent upon the Te position. The analogue with Te at position 5 showed the most pronounced (5-min values) heart uptake (3.7-4.1 dose/g), myocardial retention, and heart/blood ratios (37:1) and is a candidate for radiolabeling with /sup 123/I and further evaluation as a myocardial imaging agent.

• Research Organization: Oak Ridge National Lab., TN
• OSTI ID: 6549123
• Journal Information: J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 27:1; ISSN JMCMA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550501 -- Metabolism-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANIMALS
BETA DECAY RADIOISOTOPES
BODY
CARBOXYLIC ACIDS
CARDIOVASCULAR SYSTEM
CHEMICAL PREPARATION
CHEMISTRY
DAYS LIVING RADIOISOTOPES
DRUGS
ELECTRON CAPTURE RADIOISOTOPES
ELEMENTS
EVALUATION
HEART
HOURS LIVING RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINE 123
IODINE 125
IODINE ISOTOPES
ISOTOPES
LABELLED COMPOUNDS
LABELLING
MAMMALS
MUSCLES
MYOCARDIUM
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RADIOCHEMISTRY
RADIOISOTOPES
RADIONUCLIDE KINETICS
RADIOPHARMACEUTICALS
RATS
RETENTION
RODENTS
SEMIMETALS
SYNTHESIS
TELLURIUM
UPTAKE
VERTEBRATES