Synthesis and radioiodination of 7-(3′-ammoniopropyl)-7,8-dicarba-nido-undecaborate(-1), (ANC)

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 47; no. 9; pp. 557 - 569
• Main Authors: Ghirmai, Senait, Malmquist, Jonas, Lundquist, Hans, Tolmachev, Vladimir, Sjöberg, Stefan
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.08.2004; Wiley
• Subjects: 125I; 7-(3′-Ammoniopropyl)-7; 7‐(3′‐Ammoniopropyl)‐7,8‐dicarba‐nido‐undecaborate(‐1); 8-dicarba-nido-undecaborate(-1); ANC; Biological and medical sciences; chloramine-T; Contrast media. Radiopharmaceuticals; Medical sciences; Pharmacology. Drug treatments; radioiodination; Organic borate; Iodine 125; Cage compound; Radiolabelling; Betaine; Ammonium compound; Boron Organic compounds; Carborane; Iodine Isotopes; Chemical synthesis; Boron neutron capture therapy
• ISSN: 0362-4803; 1099-1344; 1099-1344
• DOI: 10.1002/jlcr.840

Derivatives of nido‐carborate have potential use in tumour targeting as hydrophilic boron‐rich compounds for boron neutron capture therapy (BNCT) and as pendant groups for attachment of radiohalogens to tumour‐seeking molecules. For this purpose, functionalized derivatives of nido‐carborates that can be conjugated to biomolecules should be synthesized and evaluated. In this study, racemic 1, 7‐(3′‐ammoniopropyl)‐7,8‐dicarba‐nido‐undecaborate(‐1) (acronym ANC) was obtained by degradation of the corresponding aminopropyl‐o‐carborane, which was synthesized in three steps from 1‐tert‐butyldimethylsilyl‐2‐(3‐bromopropyl)‐o‐carborane, with sodium hydroxide in absolute ethanol. The racemate 1 was radioiodinated (125I) using the Chloramine‐T method. Radio‐TLC results showed that radiolabelling with 125I was achieved in a yield greater than 95%. Copyright © 2004 John Wiley & Sons, Ltd.