title: A unique paradigm for a Turn-ON near-infrared cyanine-based probe: noninvasive intravital optical imaging of hydrogen peroxide.
abstract: The development of highly sensitive fluorescent probes in combination with innovative optical techniques is a promising strategy for intravital noninvasive quantitative imaging. Cyanine fluorochromes belong to a superfamily of dyes that have attracted substantial attention in probe design for molecular imaging. We have developed a novel paradigm to introduce a Turn-ON mechanism in cyanine molecules, based on a distinctive change in their π-electrons system. Our new cyanine fluorochrome is synthesized through a simple two-step procedure and has an unprecedented high fluorescence quantum yield of 16% and large extinction coefficient of 52,000 M(-1)cm(-1). The synthetic strategy allows one to prepare probes for various analytes by introducing a specific triggering group on the probe molecule. The probe was equipped with a corresponding trigger and demonstrated efficient imaging of endogenous hydrogen peroxide, produced in an acute lipopolysaccharide-induced inflammation model in mice. This approach provides, for the first time, an available methodology to prepare modular molecular Turn-ON probes that can release an active cyanine fluorophore upon reaction with specific analyte.
authors.affiliation: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.
authors.forename: Naama
authors.initials: N
authors.lastname: Karton-Lifshin
authors.forename: Ehud
authors.initials: E
authors.lastname: Segal
authors.forename: Liora
authors.initials: L
authors.lastname: Omer
authors.forename: Moshe
authors.initials: M
authors.lastname: Portnoy
authors.forename: Ronit
authors.initials: R
authors.lastname: Satchi-Fainaro
authors.forename: Doron
authors.initials: D
authors.lastname: Shabat
mesh_terms: D000818:Animals; D002232:Carbocyanines / Q000378:metabolism*; D005456:Fluorescent Dyes / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000378:metabolism*; D007259:Infrared Rays; D051379:Mice; D057054:Molecular Imaging / Q000379:methods*; D055620:Optical Phenomena
chemical_list: D002232:Carbocyanines; D005456:Fluorescent Dyes; D006861:Hydrogen Peroxide