The inverse electron demand Diels-Alder cycloaddition with carbon-11 and fluorine-18: A gateway to pretargeted imaging across the blood-brain barrier

J Labelled Comp Radiopharm. 2023 Jul;66(9):249-268. doi: 10.1002/jlcr.4029. Epub 2023 May 18.

Abstract

There is increased focus on developing tools to image large biomolecules, such as antibodies, within the brain using positron emission tomography (PET). The inverse electron demand Diels-Alder cycloaddition (IEDDA) reaction has offered the greatest prospect of achieving such a feat and has gained much interest over the past decade. The fast reaction kinetics of the IEDDA reaction opens up the possibility of utilising a pretargeted approach, whereby the subject is pretreated with a biomolecule that has high specificity for its target. A radiolabelled second component is then administered to the subject, enabling the biomolecule to be visualised by PET. However, for this to become common practice, there is a need for the development of either radiolabelled trans-cyclooctenes (TCOs) or tetrazines that can cross the blood-brain barrier (BBB). This review highlights the advancements in the development of both radiolabelled TCOs and tetrazines, which have been radiolabelled with either carbon-11 or fluorine-18 and show promise or have been evaluated for use in pretargeted PET imaging across the BBB.

Keywords: blood-brain barrier; carbon-11; inverse electron demand Diels-Alder reaction; pretargeted imaging; tetrazine; trans-cyclooctene.

Publication types

  • Review

MeSH terms

  • Blood-Brain Barrier*
  • Cycloaddition Reaction
  • Electrons*

Substances

  • Fluorine-18
  • Carbon-11