title: Photoswitchable Spiropyran Dyads for Biological Imaging.
abstract: The synthesis of a small-molecule dyad consisting of a far-red-emitting silicon rhodamine dye that is covalently linked to a photochromic spironaphthothiopyran unit, which serves as a photoswitchable quencher, is reported. This system can be switched reversibly between the fluorescent and nonfluorescent states using visible light at wavelengths of 405 and 630 nm, respectively, and it works effectively in aqueous solution. Live-cell imaging demonstrates that this dyad has several desirable features, including excellent membrane permeability, fast and reversible modulation of fluorescence by visible light, and good contrast between the bright and dark states.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, U.K.
authors.forename: Yaoyao
authors.initials: Y
authors.lastname: Xiong
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, U.K.
authors.forename: Pablo
authors.initials: P
authors.lastname: Rivera-Fuentes
authors.affiliation: MRC Human Immunology Unit and Wolfson Imaging Centre Oxford, Weatherall Institute of Molecular Medicine, University of Oxford , Oxford OX3 9DS, U.K.
authors.forename: Erdinc
authors.initials: E
authors.lastname: Sezgin
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, U.K.
authors.forename: Andreas
authors.initials: A
authors.lastname: Vargas Jentzsch
authors.affiliation: MRC Human Immunology Unit and Wolfson Imaging Centre Oxford, Weatherall Institute of Molecular Medicine, University of Oxford , Oxford OX3 9DS, U.K.
authors.forename: Christian
authors.initials: C
authors.lastname: Eggeling
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, U.K.
authors.forename: Harry L
authors.initials: HL
authors.lastname: Anderson
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D002470:Cell Survival; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods*; D055668:Photochemical Processes; D012235:Rhodamines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001578:Benzopyrans; D005456:Fluorescent Dyes; D007211:Indoles; D009574:Nitro Compounds; D012235:Rhodamines; C088184:spiropyran