title: Preparation of an18F-Labeled Hydrocyanine Dye as a Multimodal Probe for Reactive Oxygen Species.
abstract: Hydrocyanine dyes are sensitive "turn-on" type optical probes that can detect reactive oxygen species (ROS). We have developed a method to prepare an18F-labeled hydrocyanine dye as a multi-modal PET and optical "turn-on" probe. A commercially available near infrared (NIR) dye was modified with a fluorinated prosthetic group that did not alter its ROS sensing properties in the presence of superoxide and hydroxyl radicals. The18F-labeled analogue was produced using a single-step terminal fluorination procedure. Positron emission tomography (PET) imaging and quantitative in vivo biodistribution studies indicated this novel probe had remarkably different pharmacokinetics compared to the oxidized cyanine analogue. The chemistry reported enables the use of quantitative and dynamic PET imaging for the in vivo study of hydrocyanine dyes as ROS probes.
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Salma
authors: S
authors: Al-Karmi
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Silvia A
authors: SA
authors: Albu
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Alyssa
authors: A
authors: Vito
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Nancy
authors: N
authors: Janzen
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Shannon
authors: S
authors: Czorny
authors: Centre for Probe Development and Commercialization, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Laura
authors: L
authors: Banevicius
authors: European Molecular Biology Laboratory, Grenoble Outstation, 71 Avenue des Martyrs, CS 90181, 38042, Grenoble Cedex 9, France.
authors: Max
authors: M
authors: Nanao
authors: Department of Chemistry, Syracuse University, Syracuse, NY, 13244, USA.
authors: Jon
authors: J
authors: Zubieta
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: Alfredo
authors: A
authors: Capretta
authors: Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.|Centre for Probe Development and Commercialization, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada.
authors: John F
authors: 0000-0002-1461-552X
authors: JF
authors: Valliant
mesh_terms: D000818:Animals; D002232:Carbocyanines / Q000737:chemistry* / Q000493:pharmacokinetics; D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000493:pharmacokinetics; D005462:Fluorine Radioisotopes / Q000737:chemistry* / Q000493:pharmacokinetics; D054879:Halogenation; D006801:Humans; D051379:Mice; D049268:Positron-Emission Tomography / Q000379:methods*; D017382:Reactive Oxygen Species / Q000032:analysis*; D014018:Tissue Distribution
chemical_list: D002232:Carbocyanines; D005456:Fluorescent Dyes; D005462:Fluorine Radioisotopes; D017382:Reactive Oxygen Species; C000615276:Fluorine-18
keywords: PET; fluorescent probes; fluorine; multimodal; reactive oxygen species