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    Discovery of a Redox-activatable chemical probe for detection of cyclooxygenase-2 in cells and animals

    Date
    2022-07-15
    Author
    Uddin, Md. Jashim
    Lo, Justin Han-Je
    Oltman, Connor G.
    Crews, Brenda C.
    Huda, Tamanna
    Liu, Justin
    Kingsley, Philip J.
    Lin, Shuyang
    Milad, Mathew
    Aleem, Ansari M.
    Asaduzzaman, Abu
    McIntyre, J. Oliver
    Duvall, Craig L.
    Marnett, Lawrence J.
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    Citation
    Uddin, M. J., Lo, J. H.-J., Oltman, C. G., Crews, B. C., Huda, T., Liu, J., . . . Marnett, L. J. (2022). Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals. ACS Chemical Biology, 17(7), 1714-1722. https://doi.org/10.1021/acschembio.1c00961
    Abstract
    Cyclooxygenase-2 (COX-2) expression is up-regulated in inflammatory tissues and many premalignant and malignant tumors. Assessment of COX-2 protein in vivo, therefore, promises to be a powerful strategy to distinguish pathologic cells from normal cells in a complex disease setting. Herein, we report the first redox-activatable COX-2 probe, fluorocoxib Q (FQ), for in vivo molecular imaging of pathogenesis. FQ inhibits COX-2 selectively in purified enzyme and cell-based assays. FQ exhibits extremely low fluorescence and displays time- and concentration-dependent fluorescence enhancement upon exposure to a redox environment. FQ enters the cells freely and binds to the COX-2 enzyme. FQ exhibits high circulation half-life and metabolic stability sufficient for target site accumulation and demonstrates COX-2-targeted uptake and retention in cancer cells and pathologic tissues. Once taken up, it undergoes redox-mediated transformation into a fluorescent compound fluorocoxib Q-H that results in high signal-to-noise contrast and differentiates pathologic tissues from non-pathologic tissues for real-time in vivo imaging.
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    URI
    https://doi.org/10.1021/acschembio.1c00961
    https://soar.wichita.edu/handle/10057/23611
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