title: An ICT-based approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells.
abstract: We present the synthesis, properties, and biological applications of Peroxy Lucifer 1 (PL1), a new fluorescent probe for imaging hydrogen peroxide produced in living cells by a ratiometric response. PL1 utilizes a chemoselective boronate-based switch to detect hydrogen peroxide by modulation of internal charge transfer (ICT) within a 1,8-naphthalimide dye. PL1 features high selectivity for hydrogen peroxide over similar reactive oxygen species, including superoxide, and nitric oxide, and a 65 nm shift in emission from blue-colored fluorescence to green-colored fluorescence upon reaction with peroxide. Two-photon confocal microscopy experiments in live macrophages show that PL1 can ratiometrically visualize localized hydrogen peroxide bursts generated in living cells at immune response levels.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Duangkhae
authors.initials: D
authors.lastname: Srikun
authors.forename: Evan W
authors.initials: EW
authors.lastname: Miller
authors.forename: Dylan W
authors.initials: DW
authors.lastname: Domaille
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Chang
mesh_terms: D000818:Animals; D002219:Carbamates / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000494:pharmacology; D006861:Hydrogen Peroxide / Q000032:analysis / Q000378:metabolism*; D007546:Isoquinolines / Q000737:chemistry; D008264:Macrophages / Q000378:metabolism*; D051379:Mice; D018613:Microscopy, Confocal / Q000379:methods; D013050:Spectrometry, Fluorescence
chemical_list: D002219:Carbamates; D005456:Fluorescent Dyes; D007546:Isoquinolines; C017475:lucifer yellow; D006861:Hydrogen Peroxide