title: New Red-Emitting Tetrazine-Phenoxazine Fluorogenic Labels for Live-Cell Intracellular Bioorthogonal Labeling Schemes.
abstract: The synthesis of a set of tetrazine-bearing fluorogenic dyes suitable for intracellular labeling of proteins in live cells is presented. The red excitability and emission properties ensure minimal autofluorescence, while through-bond energy-transfer-based fluorogenicity reduces nonspecific background fluorescence of unreacted dyes. The tetrazine motif efficiently quenches fluorescence of the phenoxazine core, which can be selectively turned on chemically upon bioorthogonal inverse-electron-demand Diels-Alder reaction with proteins modified genetically with strained trans-cyclooctenes.
authors.affiliation: Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: Gergely
authors.initials: G
authors.lastname: Knorr
authors.affiliation: Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: Eszter
authors.initials: E
authors.lastname: Kozma
authors.affiliation: Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary.
authors.forename: András
authors.initials: A
authors.lastname: Herner
authors.affiliation: Structural and Computational Biology Unit, Cell Biology and Biophysics Unit, European Molecular Biology Laboratory, Meyerhofstrasse 1, 69117, Heidelberg, Germany.
authors.forename: Edward A
authors.initials: EA
authors.lastname: Lemke
authors.affiliation: Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary. kele.peter@ttk.mta.hu.
authors.forename: Péter
authors.initials: P
authors.lastname: Kele
mesh_terms: D061565:Cycloaddition Reaction; D005456:Fluorescent Dyes / Q000737:chemistry; D049452:Green Fluorescent Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D057809:HEK293 Cells; D006571:Heterocyclic Compounds / Q000737:chemistry; D006801:Humans; D018613:Microscopy, Confocal; D010078:Oxazines / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D006571:Heterocyclic Compounds; D010078:Oxazines; D049452:Green Fluorescent Proteins; C039203:phenoxazine
keywords: dyes/pigments; energy transfer; fluorescent probes; imaging agents; proteins