New myocardial imaging agents: stabilization of radioiodine as a terminal vinyl iodide moiety on tellurium fatty acids

J Med Chem. 1983 Sep;26(9):1293-300. doi: 10.1021/jm00363a014.

Abstract

To determine the myocardial uptake and retention properties of radioiodinated tellurium fatty acids, we prepared two new tellurium fatty acids in which iodine-125 has been chemically stabilized by attachment as a trans-vinyl iodide (I-CH = CH-R-Te-R'-COOH) and evaluated them in rats. Fabrication of 18-iodo-13-tellura-17-octadecenoic acid was accomplished by coupling 1,5-diiodo-1-pentene with sodium 12-(methoxycarbonyl)-n-dodecan-1-yl telluride. The [5-125I]-1,5-diiodo-1-pentene was prepared by an organoborane technique involving 125I+ treatment of 5-iodo-1-penten-1-ylboronic acid [I(CH2)3CH = CHB(OH)2]. The absolute heart uptake of this agent was moderate (1.47-2.52% dose/g after 60 min), but the heart/blood ratios were low (approximately 2.6:1). Only marginal in vivo deiodination occurred, since the thyroid uptake was low (15-18% dose/g after 60 min). The effect of tellurium in position 13 was unexpected. To determine if the low heart specificity and low heart/blood ratios were dependent upon the position of the tellurium, we prepared an analogue with the same chain length, 18-[125I]iodo-7-tellura-17-octadecenoic acid, in the same manner by reaction of [11-125I]-1,11-diiodo-1-undecene with sodium 6-(methoxycarbonyl)-n-hexan-1-yl telluride. This agent showed pronounced heart uptake (2.47-3.94% dose/g after 60 min) and prolonged retention (1.76-3.14% dose/g after 4 h) in rats. Furthermore, the heart/blood ratios remained high for several hours (13:1 after 60 min; 9:1 after 4 h). Iodine-123 labeled 18-iodo-7-tellura-17-octadecenoic acid is an attractive new compound for evaluation as a myocardial imaging agent.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Female
  • Heart / diagnostic imaging*
  • Iodine Radioisotopes
  • Myocardium / metabolism
  • Oleic Acids / chemical synthesis
  • Oleic Acids / metabolism*
  • Radionuclide Imaging
  • Rats
  • Rats, Inbred F344
  • Tellurium / chemical synthesis
  • Tellurium / metabolism*
  • Tissue Distribution

Substances

  • Iodine Radioisotopes
  • Oleic Acids
  • 18-iodo-13-tellura-17-octadecenoic acid
  • 18-iodo-7-tellura-17-octadecenoic acid
  • Tellurium