title: Copper Catalysis in Living Systems and In Situ Drug Synthesis.
abstract: The copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has proven to be a pivotal advance in chemical ligation strategies with applications ranging from polymer fabrication to bioconjugation. However, application in vivo has been limited by the inherent toxicity of the copper catalyst. Herein, we report the application of heterogeneous copper catalysts in azide-alkyne cycloaddition processes in biological systems ranging from cells to zebrafish, with reactions spanning from fluorophore activation to the first reported in situ generation of a triazole-containing anticancer agent from two benign components, opening up many new avenues of exploration for CuAAC chemistry.
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, EH9 3FJ, Edinburgh, UK.
authors.forename: Jessica
authors.initials: J
authors.lastname: Clavadetscher
authors.affiliation: University of Edinburgh/BHF Centre for Cardiovascular Science, Queen's Medical Research Institute, 47 Little France Crescent, EH16 4TJ, Edinburgh, UK.
authors.forename: Scott
authors.initials: S
authors.lastname: Hoffmann
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, EH9 3FJ, Edinburgh, UK.
authors.forename: Annamaria
authors.initials: A
authors.lastname: Lilienkampf
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, EH9 3FJ, Edinburgh, UK.
authors.forename: Logan
authors.initials: L
authors.lastname: Mackay
authors.affiliation: School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600, Bangi, Selangor, Malaysia.
authors.forename: Rahimi M
authors.initials: RM
authors.lastname: Yusop
authors.affiliation: University of Edinburgh/BHF Centre for Cardiovascular Science, Queen's Medical Research Institute, 47 Little France Crescent, EH16 4TJ, Edinburgh, UK.
authors.forename: Sebastien A
authors.initials: SA
authors.lastname: Rider
authors.affiliation: University of Edinburgh/BHF Centre for Cardiovascular Science, Queen's Medical Research Institute, 47 Little France Crescent, EH16 4TJ, Edinburgh, UK.
authors.forename: John J
authors.initials: JJ
authors.lastname: Mullins
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, EH9 3FJ, Edinburgh, UK.
authors.forename: Mark
authors.initials: M
authors.lastname: Bradley
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002460:Cell Line; D057930:Click Chemistry / Q000379:methods*; D003300:Copper; D061565:Cycloaddition Reaction / Q000379:methods*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D053768:Metal Nanoparticles / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*; D015027:Zebrafish
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D001386:Azides; D005456:Fluorescent Dyes; D014230:Triazoles; D003300:Copper
keywords: bioorthogonal chemistry; copper; heterogeneous catalysis; prodrugs