Syntheses of o-iodobenzyl alcohols‒BODIPY structures as potential precursors of bimodal tags for positron emission tomography and optical imaging. Issue 52 (27th December 2019)

• Record Type: Journal Article
• Authors: Christine, Thifanie; Tabey, Alexis; Cornilleau, Thomas; Fouquet, Eric; Hermange, Philippe
• Is Part Of: Tetrahedron. Volume 75:Issue 52(2019)
• Publication Date: 2019-12-27
• Subjects: Positron emission tomograpy -- Fluorescence imaging -- Multimodal tracer -- BODIPY -- Carbonylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130765
• Languages: English
• ISSNs: 0040-4020

Abstract

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 11 C-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. Graphical abstract: Image 1 Highlights: Design and synthesis of a promising o -iodobenzyl alcohol-BODIPY tag for multimodal imaging (fluorescence / 11 C-labeling).