Preparation of an F-18-Labeled Hydrocyanine Dye as a Multimodal Probe for Reactive Oxygen Species

Hydrocyanine dyes are sensitive "turn-on" type optical probes that can detect reactive oxygen species (ROS). We have developed a method to prepare an F-18-labeled hydrocyanine dye as a multi-modal PET and optical "turn-on" probe. A commercially available near infrared (NIR) dye w...

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Published inChemistry : a European journal Vol. 23; no. 2; pp. 254 - 258
Main Authors Al-Karmi, Salma, Albu, Silvia A., Vito, Alyssa, Janzen, Nancy, Czorny, Shannon, Banevicius, Laura, Nanao, Max, Zubieta, Jon, Capretta, Alfredo, Valliant, John F.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.01.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIDATIVE STRESS
SUPEROXIDE
REVERSIBLE FLUORESCENT-PROBE
ACID
multimodal
IMAGING HYDROGEN-PEROXIDE
fluorescent probes
HYDROXYL RADICALS
reactive oxygen species
SELECTIVE DETECTION
HEPTAMETHINE CYANINE DYES
PET
fluorine
LIVING CELLS
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Summary:Hydrocyanine dyes are sensitive "turn-on" type optical probes that can detect reactive oxygen species (ROS). We have developed a method to prepare an F-18-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. The 18F-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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201604473