83816-56-2Relevant academic research and scientific papers
Radioiodine-Labeled N,N-Dimethyl-N'-(2-hydroxy-3-alkyl-5-iodobenzyl)-1,3-propanediamines for Brain Perfusion Imaging
Tramposch, Kenneth M.,Kung, Hank F.,Blau, Monte
, p. 121 - 125 (2007/10/02)
In developing new brain-imaging agents for single photon emission computed tomography (SPECT), we synthesized five radioiodinated N,N-dimethyl-N'-(2-hydroxy-3-alkyl-5-iodobenzyl)-1,3-propanediamines (12-16).The appropriate o-alkylphenol was formylated via a tin(IV) chloride catalyzed reaction.Iodination with iodine monochloride gave the required 3-alkyl-5-iodosalicylaldehyde, which was reductively aminated with 3-(dimethylamino)propylamine and sodium borohydride.The radioactive labeling (>95percent yield) can be achieved by a rapid aqueous exchange reaction in a serum vial at 100 deg C.Biodistribution in rats exhibited high initial brain uptake (0.9 to 1.8percent dose in brain at 2 min), and the brain activity remained about the same at 1 h for all the compounds.The best brain-imaging agent was N,N-dimethyl-N'-(2-hydroxy-3-methyl-5-iodobenzyl)-1,3-propanediamine (12), which showed the highest uptake of 1.80 and 2.02percent dose in brain at 2 min and 1 h, respectively.The brain uptake increases when the specific activity of 125I-labeled 12 decreases.An imaging study of 12 in a monkey showed high initial brain uptake as well as high uptake in lungs and liver.The brain uptake persists for at least 1 h.Autoradiography of rat brain sections showed a regional distribution that reflects the cerebral perfusion pattern (high activity in gray matter and low activity in white matter).It is apparent that 12 is readily prepared and is potentially useful for brain perfusion imaging in conjunction with SPECT devices.
