title: Photoelectrocyclization as an activation mechanism for organelle-specific live-cell imaging probes.
abstract: Photoactivatable fluorophores are useful tools in live-cell imaging owing to their potential for precise spatial and temporal control. In this report, a new photoactivatable organelle-specific live-cell imaging probe based on a 6π electrocyclization/oxidation mechanism is described. It is shown that this new probe is water-soluble, non-cytotoxic, cell-permeable, and useful for mitochondrial imaging. The probe displays large Stokes shifts in both pre-activated and activated forms, allowing simultaneous use with common dyes and fluorescent proteins. Sequential single-cell activation experiments in dense cellular environments demonstrate high spatial precision and utility in single- or multi-cell labeling experiments.
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 (USA).
authors.forename: Mai N
authors.initials: MN
authors.lastname: Tran
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 (USA). dcheno@sas.upenn.edu.
authors.forename: David M
authors.initials: DM
authors.lastname: Chenoweth
mesh_terms: D003500:Cyclization; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D008164:Luminescent Proteins / Q000737:chemistry / Q000378:metabolism; D008856:Microscopy, Fluorescence; D008928:Mitochondria / Q000378:metabolism / Q000473:pathology*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014965:X-Rays
chemical_list: D005456:Fluorescent Dyes; D008164:Luminescent Proteins
keywords: electrocyclization; fluorescent probes; imaging agents; photochemistry