title: Carbofluoresceins and carborhodamines as scaffolds for high-contrast fluorogenic probes.
abstract: Fluorogenic molecules are important tools for advanced biochemical and biological experiments. The extant collection of fluorogenic probes is incomplete, however, leaving regions of the electromagnetic spectrum unutilized. Here, we synthesize green-excited fluorescent and fluorogenic analogues of the classic fluorescein and rhodamine 110 fluorophores by replacement of the xanthene oxygen with a quaternary carbon. These anthracenyl "carbofluorescein" and "carborhodamine 110" fluorophores exhibit excellent fluorescent properties and can be masked with enzyme- and photolabile groups to prepare high-contrast fluorogenic molecules useful for live cell imaging experiments and super-resolution microscopy. Our divergent approach to these red-shifted dye scaffolds will enable the preparation of numerous novel fluorogenic probes with high biological utility.
authors.affiliation: Janelia Farm Research Campus, Howard Hughes Medical Institute , Ashburn, Virginia, 20147, United States.
authors.forename: Jonathan B
authors.initials: JB
authors.lastname: Grimm
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Sung
authors.forename: Wesley R
authors.initials: WR
authors.lastname: Legant
authors.forename: Phuson
authors.initials: P
authors.lastname: Hulamm
authors.forename: Sylwia M
authors.initials: SM
authors.lastname: Matlosz
authors.forename: Eric
authors.initials: E
authors.lastname: Betzig
authors.forename: Luke D
authors.initials: LD
authors.lastname: Lavis
mesh_terms: D002244:Carbon / Q000737:chemistry; D002470:Cell Survival; D019793:Fluorescein / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D018613:Microscopy, Confocal; D012235:Rhodamines / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D014966:Xanthenes / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D012235:Rhodamines; D014966:Xanthenes; C049025:rhodamine 110; D002244:Carbon; D019793:Fluorescein
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