Potential tumor- or organ-imaging agents. 23. Sterol esters of iopanoic acid

A series of sterol esters of iopanoic acid was synthesized and evaluated for their potential to selectively localize in liver and steroid-secreting tissues for possible application in either computed tomography or nuclear medicine imaging. Unlike free iopanoic acid (1), which was rapidly cleared fol...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1982-12, Vol.25 (12), p.1500-1503
Main Authors: Seevers, R. H, Groziak, M. P, Weichert, J. P, Schwendner, S. W, Szabo, S. M, Longino, M. A, Counsell, R. E
Format: Article
Language:English
Subjects:
Animals
Blood Protein Electrophoresis
Contrast Media - chemical synthesis
Dogs
Female
Iopanoic Acid - analogs & derivatives
Iopanoic Acid - chemical synthesis
Iopanoic Acid - metabolism
Neoplasms - diagnostic imaging
Rabbits
Radiography
Radionuclide Imaging
Rats
Rats, Inbred Strains
Tissue Distribution
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Summary:A series of sterol esters of iopanoic acid was synthesized and evaluated for their potential to selectively localize in liver and steroid-secreting tissues for possible application in either computed tomography or nuclear medicine imaging. Unlike free iopanoic acid (1), which was rapidly cleared following intravenous administration to rats, cholesteryl iopanoate (2) was found to accumulate in liver, adrenal cortex, and ovary. At 24 h, the ovary was found to contain the highest concentration of 2. The ability of 2 to accumulate in the above tissues was attributed to its resistance to hydrolysis. Pregnenolone iopanoate (3) and dehydroepiandrosterone iopanoate (4), on the other hand, were shown to reach unusually high concentrations in the adrenal cortex within 0.5 h of administration but declined to much lower levels by 24 h. Lipid extraction of tissues showed 3 and 4 to be susceptible to in vivo hydrolysis, which undoubtedly was a major factor in their clearance from adrenal tissue.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00354a022