title: Tetrazine-Responsive Self-immolative Linkers.
abstract: Molecules that undergo activation or modulation following the addition of benign external small-molecule chemical stimuli have numerous applications. Here, we report the highly efficient "decaging" of a variety of moieties by activation of a "self-immolative" linker, by application of water-soluble and stable tetrazine, including the controlled delivery of doxorubicin in a cellular context.
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Kevin
authors.initials: K
authors.lastname: Neumann
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Sarthak
authors.initials: S
authors.lastname: Jain
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Alessia
authors.initials: A
authors.lastname: Gambardella
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Walker
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Elsa
authors.initials: E
authors.lastname: Valero
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Annamaria
authors.initials: A
authors.lastname: Lilienkampf
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.
authors.forename: Mark
authors.initials: M
authors.lastname: Bradley
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D061565:Cycloaddition Reaction; D004317:Doxorubicin / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity; D004337:Drug Carriers / Q000737:chemistry*; D065546:Drug Liberation; D057809:HEK293 Cells; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D006801:Humans; D053758:Nanoparticles / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry
chemical_list: D004337:Drug Carriers; D006573:Heterocyclic Compounds, 1-Ring; D011092:Polyethylene Glycols; D004317:Doxorubicin
keywords: Diels-Alder reaction; doxorubicin; nanoparticles; prodrugs; tetrazine