Preparation and evaluation of reagents for tagging amino and thiol groups with fluorous stannanes. A convenient method for producing radioiodinated compounds in high effective specific activity

Abstract Building on the previously reported fluorous labeling strategy (FLS), a new approach for preparing molecular imaging and therapy agents derived from radioiodine in high purity without the need to employ HPLC was developed. A series of novel reagents containing a fluorous arylstannane, including fluorous benzaldehydes ( 1a/b ) and an aryl‐iodoacetamide ( 2 ), were prepared so that the FLS could be used to label and purify targeting vectors that contain free amines or thiol groups. The reagents were conjugated to model amines and thiols in generally high yields (79–95%) under mild conditions. The fully characterized products were radiolabeled with Na[ 125 I] in the presence of iodogen and the products were purified using fluorous solid‐phase extraction to yield the desired iodinated products in high yield (>83%) and high effective specific activity (ESA). The work reported creates a convenient and flexible means of preparing targeted molecular imaging and therapy agents derived from radioisotopes of iodine in high ESA. Copyright © 2010 John Wiley & Sons, Ltd.