Syntheses of o-iodobenzyl alcohols‒BODIPY structures as potential precursors of bimodal tags for positron emission tomography and optical imaging

Abstract

Aiming the faster development from bench to bedside of new potential tracers, multimodal tracers for positron emission tomography (PET) and optical imaging (OI) have emerged as a very promising tool. Indeed, they combine the simplicity of use of optical techniques for in vitro/in vivo pre-clinical studies with the various clinical possibilities offered by PET imaging using their radioactive versions. In this context, the preparation of new tags detectable by fluorescence imaging and potentially suitable for PET imaging after a last-step 11C-labeling of the corresponding precursor has been investigated. Various designs and syntheses were explored by linking o-iodobenzyl alcohols and tetramethyl-BODIPY moieties together. Among them, the most promising structure was produced in 30% yield over five steps from a commercially available and inexpensive starting material.