Synthesis and evaluation of 24-(isopropyl[75Se]seleno)chol-5-en-3β-ol

• Published in: Journal of medicinal chemistry 1983-10, Vol.26 (10), p.1538-1541
• Main Authors: KNAPP, F. F. JR, BUTLER, T. A, FERREN, L. A, CALLAHAN, A. P, GUYER, C. E, COFFEY, J. L
• Format: Article
• Language: English
• Subjects: Adrenal Glands - metabolism; Alicyclic compounds, terpenoids, prostaglandins, steroids; Animals; Chemistry; Cholenes - chemical synthesis; Cholenes - metabolism; Exact sciences and technology; Female; Indicators and Reagents; Kidney - metabolism; Kinetics; Liver - metabolism; Mass Spectrometry; Organic chemistry; Organoselenium Compounds; Ovary - metabolism; Preparations and properties; Radioisotopes; Radionuclide Imaging - methods; Rats; Selenium - chemical synthesis; Selenium - metabolism; Spectrophotometry, Infrared; Steroids; Tissue Distribution
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00364a035

Selenium-75-labeled 24-(isopropylseleno)chol-5-en-3 beta-ol (4) has been prepared by reaction of sodium isopropyl-[75Se]selenol [( 75Se]2) with 3 beta-acetoxy-24-bromochol-5-ene (3). This new 75Se-labeled adrenal imaging agent shows pronounced adrenal uptake in rats. The concentration of radioactivity in rat adrenals increased steadily from 1 to 24 h after injection and then decreased slowly over the 21-day period. After 3 days the adrenal/blood and adrenal/liver ratios were 85:1 and 32:1, respectively, which are sufficient for adrenal imaging by single photon techniques. After 6 h the adrenal/blood ratio was 17:1 and the adrenal/liver ratio was 7:1. We propose that these ratios are sufficiently high for positron emission tomography of the adrenals. The absorbed radiation dose values to human organs have been estimated for the 75Se- and 73Se-labeled agent.