Diels-Alder Cycloaddition Click Chemistry

Immuno-polymeric nanoparticles by Diels-Alder chemistry.

Diels-Alder cycloaddition strategy for kinetic resolution of chiral pyrazolidinones.

A rare example of the application of a catalytic, enantioselective Diels-Alder cycloaddition to affect a kinetic resolution has been developed. Chiral pyrazolidinones are resolved with high selectivity through a process that utilizes a relay of stereochemical information from a permanent chiral center to a fluxional chiral center to enhance the inherent selectivity of the chiral Lewis acid cata...

18F-Based Pretargeted PET Imaging Based on Bioorthogonal Diels–Alder Click Chemistry

A first-of-its-kind (18)F pretargeted PET imaging approach based on the bioorthogonal inverse electron demand Diels-Alder (IEDDA) reaction between tetrazine (Tz) and trans-cyclooctene (TCO) is presented. As proof-of-principle, a TCO-bearing immunoconjugate of the anti-CA19.9 antibody 5B1 and an Al[(18)F]NOTA-labeled tetrazine radioligand were harnessed for the visualization of CA19.9-expressing...

A pretargeted PET imaging strategy based on bioorthogonal Diels-Alder click chemistry.

UNLABELLED The specificity of antibodies have made immunoconjugates promising vectors for the delivery of radioisotopes to cancer cells; however, their long pharmacologic half-lives necessitate the use of radioisotopes with long physical half-lives, a combination that leads to high radiation doses to patients. Therefore, the development of targeting modalities that harness the advantages of ant...

Specific Binding of Liposomal Nanoparticles through Inverse Electron‐Demand Diels–Alder Click Chemistry

Here, we report a method to specifically bind liposomal radiopharmaceuticals to a CoCrMo alloy, which can be used in arterial stents, via an irreversible inverse electron-demand Diels-Alder reaction. Inspired by recent accomplishments in pre-targeted imaging using tetrazine-trans-cyclooctene click chemistry, we synthesized 89Zr-labeled trans-cyclooctene-functionalized liposomal nanoparticles, w...