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    AuthorCosentino, L. (1)Errington, R.J. (1)Lizano, E. (1)
    Pors, Klaus (1)
    Pujol, M.D. (1)Ribeiro Morais, Goreti (1)Sadiq, M. (1)Sadiq, O. (1)Sini, Marcella (1)Wiltshire, M. (1)Subject
    Anthraquinone (1)
    Cancer (1)
    CYP1A2 (1)
    Cytochrome P450 (1)
    DRAQ5 (1)Fluorophore (1)MMDX (1)Nemorubicin (1)View MoreDate Issued
    2018 (1)

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    Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones

    Errington, R.J.; Sadiq, M.; Cosentino, L.; Wiltshire, M.; Sadiq, O.; Sini, Marcella; Lizano, E.; Pujol, M.D.; Ribeiro Morais, Goreti; Pors, Klaus (2018-05-01)
    Structural features from the anticancer prodrug nemorubicin (MMDX) and the DNA-binding molecule DRAQ5™ were used to prepare anthraquinone-based compounds, which were assessed for their potential to interrogate cytochrome P450 (CYP) functional activity and localisation. 1,4-disubstituted anthraquinone 8 was shown to be 5-fold more potent in EJ138 bladder cancer cells after CYP1A2 bioactivation. In contrast, 1,5-bis((2-morpholinoethyl)amino) substituted anthraquinone 10 was not CYP-bioactivated but was shown to be fluorescent and subsequently photo-activated by a light pulse (at a bandwidth 532–587 nm), resulting in punctuated foci accumulation in the cytoplasm. It also showed low toxicity in human osteosarcoma cells. These combined properties provide an interesting prospective approach for opto-tagging single or a sub-population of cells and seeking their location without the need for continuous monitoring.
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