Premium
Synthesis, Characterisation, and Biodistribution of Radioiodinated C‐Hydroxy‐Carboranes
Author(s) -
ElZaria Mohamed E.,
Janzen Nancy,
Blacker Megan,
Valliant John F.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200833
Subject(s) - biodistribution , chemistry , bifunctional , ligand (biochemistry) , radiochemistry , yield (engineering) , carboxylic acid , nuclear chemistry , stereochemistry , organic chemistry , in vitro , biochemistry , materials science , receptor , metallurgy , catalysis
The synthesis, radiolabelling and biodistribution of iodinated C‐hydroxy‐ nido ‐carborane ligands is described. Microwave heating by using NaF in aqueous ethanol was used to prepare {sodium [7‐hydroxy‐7,8‐dicarba‐ nido ‐undecaborate], nido ‐carboranol} and {sodium [7‐hydroxy‐7,8‐dicarba‐ nido ‐undecaborate‐8‐carboxylic acid], nido ‐salborin} in 97 and 90 % yield, respectively. Radioiodination of these nido ‐carboranes was completed by using both 125 I and 123 I, and the products were obtained in high radiochemical purity (>99 %) and yield (72 to 87 %). The structures of the radiolabelled products were validated through comparison to authentic standards. Biodistribution studies in BALB/c mice showed low accumulation of the labelled compounds in the liver and intestines, which are sites where labelled carboranes typically localise. The labelled cluster bearing hydroxy and carboxylic acid groups on the two carbon vertices demonstrated preferential clearance through the kidneys and low thyroid uptake. This compound had substantially reduced non‐specific binding than the deshydroxy analogue making it an attractive bifunctional ligand for preparing targeted molecular imaging and therapy agents.